The Preparation of Glycamines<sup>1</sup>

Kagan, Fred; Rebenstorf, Melvin A.; Heinzelman, R. V.

doi:10.1021/ja01570a063

Cited by 43 publications

(23 citation statements)

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“…Paradoxalement, alors m&me que les amino-sucres sont l'objet d'un grand intCrCt et que de nouveaux sucres carbonyles sont regulierement rendus disponibles, l'amination reductrice n'est pas citke comme technique de preparation des aminosucres dans les revues les plus exhaustives de la question [2]. A notre connaissance, si Yon excepte quelques applications de la technique a la synthese d'aminodesoxyalditols [3] [4], l'amination reductrice n'a pas bte utiliske en chimie des sucres.…”

Section: Discussionunclassified

Utilisation de techniques d'amination réductrice pour la synthèse d'amino‐sucres de différents types. Communication préliminaire

Tronchet

Baehler

Zumwald

1977

Helvetica Chimica Acta

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Synthesis of amino-sugars using reductive amination reactions. Preliminary communication SummaryTreatment of aldehydo-or keto-sugars with primary or secondary amines and hydrogen in the presence of a catalyst (Pd/C) gave with good to excellent yields (67-96%) the expected secondary or tertiary amines. Primary amines can be obtained by using benzylamine, a hydrogenolysis taking place during the reaction. L'amination reductrice ou alkylation reductrice est une methode synthetique [HI bien connue (pour une revue, voir [ 11) repondant au schema suivant: RCOR' + R"NH2 A RCH (R') NHR" . Cette technique de preparation des amines partir d'un compose carbonylt est simple et d'une mise en ceuvre facile.Paradoxalement, alors m&me que les amino-sucres sont l'objet d'un grand intCrCt et que de nouveaux sucres carbonyles sont regulierement rendus disponibles, l'amination reductrice n'est pas citke comme technique de preparation des aminosucres dans les revues les plus exhaustives de la question [2]. A notre connaissance, si Yon excepte quelques applications de la technique a la synthese d'aminodesoxyalditols [3] [4], l'amination reductrice n'a pas bte utiliske en chimie des sucres.Nous nous proposons de montrer ci-dessous que cette methode est plus interessante que les techniques classiques de synthese de sucres portant un groupement amino libre a partir de sucres carbonyles (reduction d'oximes ou d'hydrazones) mais que surtout elle permet d'introduire en un seul stade dans une molecule de sucre toute une varietk de fonctions amine differemment substituees. Pour prouver la generalite de la methode, nous l'avons appliquee a un bon nombre de types de sucres carbonyles. Nous avons ainsi utilisk des derives de pentodialdofurannoses (1 [5] et 2 [6]), d'un desoxy-5-hexodialdofurannose (4), compose nouveau, egalement prepare au laboratoire [7] par d'autres voies de celle mise en ceuvre dans ce travail (reduction en C ( 5 ) et oxydation en C (6) de 3 [8]), d'un hexodialdopyran-I ) Une communication plus detaillee paraitra ultkrieurement.

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Section: Discussionunclassified

Utilisation de techniques d'amination réductrice pour la synthèse d'amino‐sucres de différents types. Communication préliminaire

Tronchet

Baehler

Zumwald

1977

Helvetica Chimica Acta

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“…All the substituted xylamines and glucamines were prepared by following a reported procedure (47) with some variation (34). In general, for Schiff base formation, D-(+)xylose (6) or a-D-(+)-glucose (9) is allowed to react with a slight excess (ca.…”

Section: Methodsmentioning

confidence: 99%

Structural Factors in the In Vivo Chelate Mobilization of Aged Cadmium Deposits

Singh¹,

Jones²,

Jones³

1990

Environmental Health Perspectives

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The role of structural factors in determining the relative efficacy of dithiocarbamates as chelating agents for the in vivo mobilization of aged cadmium deposits is examined for 23 newly synthesized compounds of this type. The critical feature in determining the efficacy of the compounds in mobilizing intracellular cadmium is the balance between hydrophobic and hydrophilic groups. This balance also governs the other properties of these compounds such as the organ specificity of action and the relative propensity to carry cadmium to the brain. The transport of cadmium to the brain by dithiocarbamate can be greatly reduced by the incorporation of appropriate hydrophilic groups that prevent the formation of lipid-soluble cadmium complexes that pass readily into the brain. If the chelating agents carry an additional ionic charge, their ability to pass through cellular membranes and react with intracellular deposits of cadmium is significantly reduced, with other structural factors being equal. The structural features that optimize mobilization of cadmium from the kidney do not appear to be identical with those that optimize its mobilization from the liver. The correlation of cadmiummobilizing properties of these chelating agents with the sum of the Hansch n constants for the parts of the molecular structures other than the dithiocarbamate grouping (lIn) is reasonably good for the removal of renal cadmium by derivatives of D-glucamine and D-xylamine. Another aspect of the molecular structure that appears to play a role is the presence of uncharged polar groups having the ability to form hydrogen bonds. The relevance ofthese factors in designing chelating agents to enhance the excretion of other toxic metals from their intracellular sites is discussed.

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“…1-A4mino-1-deoxy-~-ribitol was prepared by the reductive alkylation of ammonia method of Kagan et al (5) in which D-ribose (100 g) was dissolved in liquid ammonia and hydrogenated with Raney Nickel catalyst a t 1600 p.s.i. a t 85" for 4 hours.…”

Section: I-aceta17zido-i-deoxy-d-ribitolmentioning

confidence: 99%

SYNTHESIS OF METHYL 4-ACETAMIDO-4-DEOXY-L-ERYTHROFURANOSIDE: A SUGAR WITH NITROGEN IN A FIVE-MEMBERED RING

Szarek¹,

Jones²

1964

Can. J. Chem.

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The synthesis of methyl 4-acetamido-4-deoxy-L-erythrofuranoside from D-ribose is described. The structural features that are believed to be necessary for the replacement of the ring oxygen of sugars by nitrogen are discussed.The replacement of the ring oxygen of sugars by nitrogen has been achieved recently by a number of investigators. In this laboratory 5-acetamido-5-deoxy-L-arabinopyranose* and 5-acetamido-5-deoxy-D-xylopyranose have been synthesized from L-arabinose and D-xylose, respectively (1, 2). The same compounds have been obtained independently by Hanessian and Haskell (3). T h e latter compound has also been synthesized by a somewhat different route by Paulsen in Germany (4). In that work the compound mas named 5-acetamido-5-deoxy-D-xylopiperidinose. Chemical Abstracts recommended the nomenclature used in the present paper.All of the work cited above involved the introduction of nitrogen into pyranose rings. The present publication describes the synthesis of methyl 4-acetamido-4-deoxy-L-erythrofuranoside, a sugar derivative with nitrogen as the hetero atom in a five-membered ring.1-Amino-1-deoxy-D-ribitol was prepared from D-ribose by the reductive alkylation of ammonia method of Kagan et al. (5) and purified through the crystalline salicylidene Schiff base. N-Acetylation of the pure 1-amino-1-deoxy-D-ribitol with aqueous acetic anhydride then gave 1-acetamido-1-deoxy-D-ribitol (I) (6). Schwarz (7) has shown that the oxidation of mannitol, dulcitol, and sorbitol with a limited quantity of sodium metaperiodate involved preferential attack on threo-glycol groups (i.e., "trans1'-glycol groups on t h e Fischer convention). These results suggested that sodium metaperiodate would oxidize 1-acetamido-1-deoxy-D-ribitol (I) initially between C-4 and C-5, and that a large excess of the ribitol derivative would diminish further oxidation of the initial fission product. Consequently, 1 mole of l-acetamido-ldeoxy-D-ribitol was oxidized with 0.1 mole of sodium metaperiodate. Under these conditions 81y0 of the 1-acetamido-1-deoxy-D-ribitol which was oxidized underwent oxidation between C-4 and C-5 as determined by the production of formaldehyde. Clearly, in the major carbohydrate moiety produced in the oxidation, there existed the possibility of formation of a nitrogen-containing furanose ring by ring closure of the terminal aldehyde group on t o the nitrogen atom of the amide group. A large proportion of unreacted 1-acetamido-1-deoxy-D-ribitol was removed by crystallization, and the residual colorless syrup from the periodate oxidation was treated with methanolic hydrogen chloride. Chromatographic examination of the syrupy product indicated that in addition t o 1-acetamido-1-deoxy-D-ribitol one major component and two minor components were present. The major component was separated and obtained as a yellow syrup which was a mixture of two compounds. These were separated by *Nomenclature used by Chemical Abstracts.

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The Preparation of Glycamines¹

Cited by 43 publications

References 0 publications

Utilisation de techniques d'amination réductrice pour la synthèse d'amino‐sucres de différents types. Communication préliminaire

Utilisation de techniques d'amination réductrice pour la synthèse d'amino‐sucres de différents types. Communication préliminaire

Structural Factors in the In Vivo Chelate Mobilization of Aged Cadmium Deposits

SYNTHESIS OF METHYL 4-ACETAMIDO-4-DEOXY-L-ERYTHROFURANOSIDE: A SUGAR WITH NITROGEN IN A FIVE-MEMBERED RING

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The Preparation of Glycamines1

Cited by 43 publications

References 0 publications

Utilisation de techniques d'amination réductrice pour la synthèse d'amino‐sucres de différents types. Communication préliminaire

Utilisation de techniques d'amination réductrice pour la synthèse d'amino‐sucres de différents types. Communication préliminaire

Structural Factors in the In Vivo Chelate Mobilization of Aged Cadmium Deposits

SYNTHESIS OF METHYL 4-ACETAMIDO-4-DEOXY-L-ERYTHROFURANOSIDE: A SUGAR WITH NITROGEN IN A FIVE-MEMBERED RING

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The Preparation of Glycamines¹