Hydrazinreaktionen, I. Fragmentierung von α‐Mesyloxy‐carbonsäurehydraziden. Synthese von 5‐Desoxy‐D‐<i>xylo</i>‐hexofuranuronsäurelacton

Paulsen, Hans; Stoye, Dieter

doi:10.1002/cber.19660990328

Cited by 40 publications

(3 citation statements)

References 13 publications

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“…The reaction is believed to proceed via a ketene intermediate. 20 A similar cleavage of the aziridine ring has been observed for N-alkylated aziridines. 21 Treatment of the hydrazide 13 with bromine gave the crystalline 3-amino-2,3-dideoxylactone 14 as the hydrobromide in 74% yield (Scheme 5).…”

supporting

confidence: 58%

A New Method for the Synthesis of 2,3-Aziridino-2,3-dideoxyhexonamides and Their Conversion into 3-Amino-2,3-dideoxyhexonic Acids

Jørgensen¹,

Pedersen²,

Søtofte³

1998

Synthesis

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Two new 2,3-aziridino-2,3-dideoxyhexonamides 3 and 11 were prepared by a three-step procedure from commercially available D-glucono-1,5-lactone and D-gulono-1,4-lactone, respectively. The lactones were converted into methyl 3,4:5,6-di-O-isopropylidene-2-O-mesyl esters 2 and 10, which upon treatment with ammonia formed the title aziridino compounds. These were reductively cleaved by hydrazine to give 3-amino-2,3dideoxyhexonic hydrazides 13 and 15, which were easily converted into the corresponding lactone 14 and acid 16, respectively.

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supporting

confidence: 58%

A New Method for the Synthesis of 2,3-Aziridino-2,3-dideoxyhexonamides and Their Conversion into 3-Amino-2,3-dideoxyhexonic Acids

Jørgensen¹,

Pedersen²,

Søtofte³

1998

Synthesis

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“…The organic solution was washed with brine, dried over sodium sulfate, and filtered. Subsequent filtration through silica gel provided 25 (250 mg, 30% yield). IR (film): 1790, 1387, 1165 cm -1 .…”

Section: Methodsmentioning

confidence: 99%

Regio- and Diastereoselective Allenylation of Aldehydes in Aqueous Media: Total Synthesis of (+)-Goniofufurone¹

Meng

Hua

et al. 1998

J. Org. Chem.

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The regio- and diastereoselectivities of metal-mediated allenylation of carbonyl compounds were investigated in aqueous media. Different metal mediators showed varied regioselectivities on product formation during propargylation-allenylation reactions of carbonyl compounds with simple propargyl bromide. Under the standard reaction conditions, the use of indium provided the highest regioselectivity, with a preference of formation of the homopropargyl alcohol. The use of tin and bismuth as the metal mediator provided slightly lower selectivities with the same preference. The use of zinc and cadmium as the mediators further lowered the product selectivity. The reactions of an aliphatic aldehyde with simple propargyl bromide showed a lower selectivity than the reaction of an aromatic aldehyde in most cases, except for the use of tin or zinc (where comparable selectivities were observed). On the other hand, the reaction of terminal-substituted propargyl bromides with aldehydes mediated by indium showed a high regioselectivity in forming allenylation products. The indium-mediated allenylation of carbonyl compounds bearing an alpha-hydroxyl group also proceeded with a high diastereoselectivity, forming syn-diols predominantly in aqueous ethanol. The high diastereoselectivity in allenylation of alpha-hydroxyl-substituted aldehydes was attributed to the chelation effect exhibited by the alpha-hydroxyl substitutent. Through the use of this highly diastereoselective allenylation, (+)-goniofufurone was synthesized from D-glucurono-6,3-lactone.

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“…The extract was shaken with charcoal, dried, and filtered through a short alumina column. Concentration of the filtrate gave crystals of thequinoxaline derivative of 2S-methoxytetrahydropyran-3,4-dione (10) (b) The pentopyranosid-2-ulose (1) (1 g) was dissolved in hot ethanol (6 ml), the solution was cooled, and aqueous sodium hydroxide ( 2 . 5 ~; 0.5 ml) was added After 30 sec, phenylhydrazine (0.5 ml) was added and the mixture was boiled vigorously for 2 min.…”

Section: Treatment Of Methyl 34-o-isopropylidene-f3-~-erythro-mentioning

confidence: 99%

Synthesis of 3-amino-3,4-dideoxysugars

Collins¹,

Overend²,

Racz³

1984

J. Chem. Soc., Perkin Trans. 1

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Sequential treatment of methyl 3,4-O-isopropylidencp-L-erythro-pentopyranosidulose (1 ) with aqueous sodium hydroxide and phenylhydrazine results in elimination of acetone and formation of 2s-methoxytetrahydropyran-3,4-dione 4-phenylhydrazone (7) as the main product. Similarly, methyl 6-deoxy-3,4-0-isopropylidene-2-t-lyxo-hexopyranosid -2 -u lose (2) was converted into 2Rmethoxy -6smethyltetrahydropyran -3,4-dione 4-phenylhydrazone (8). The effect of base on the related uloside, methyl 6-deoxy-2,3-O-isopropylidene-a-L-lyxo-hexopyranosid-4-ulose (1 6), resulted in the formation of 3-hydroxy-2-methyl-4H-py~an-4-one (maltol) (1 7). Compounds (7) and (8) have been converted into, respectively, 3-amino-3,4-dideoxy-~-erythro-pentopyranose (22) and 3-amino-3,4,6-trideoxy-~ribo-hexopyranose (25).Methyl glycosiduloses have been used extensively as intermediates in the modification of sugars. Such modification is usua1.l~ at the site of the hydroxy group in a methyl glycoside at which oxidation has been effected to produce the glycosidulose. In this paper, details are provided of a sequence of reactions which results in modification at C-3 and C-4 of a methyl glycopyranosid-2-ulose derivative.' This reaction sequence provides a convenient route for the preparation of aminosugars containing the -CH2CHNH2system, as occurs in some antibiotics.2The 2-ulosides investigated in this work were methyl 3,4-O-isopropylidene-~-~-er~t~r~-pentopyranos~duIose (1) and methyl 6-deoxy-3,4-0-isopropylidene-a-~-f~~xo-hexopyranoid-2-dose (2) which were prepared in good yields by well established procedures from, respectively, L-arabinose and ~-fucose.~ I H A 1 1 ) R 1 = R 2 = H J R 3 = O M e , X = O Configuration a t C-3-C-4, L-erythro 2 1 R' = Me , R2 = OMe , R3 = H X = 0 Configuration a t C-3-C-4, D-erythro ( 3 ) R' = R2 = H , R3 = OMe, X = NNHPhAtom numbering of the compounds in this paper is based on nome:nclature and the 'H n.rn.r. data

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Hydrazinreaktionen, I. Fragmentierung von α‐Mesyloxy‐carbonsäurehydraziden. Synthese von 5‐Desoxy‐D‐xylo‐hexofuranuronsäurelacton

Cited by 40 publications

References 13 publications

A New Method for the Synthesis of 2,3-Aziridino-2,3-dideoxyhexonamides and Their Conversion into 3-Amino-2,3-dideoxyhexonic Acids

A New Method for the Synthesis of 2,3-Aziridino-2,3-dideoxyhexonamides and Their Conversion into 3-Amino-2,3-dideoxyhexonic Acids

Regio- and Diastereoselective Allenylation of Aldehydes in Aqueous Media: Total Synthesis of (+)-Goniofufurone¹

Synthesis of 3-amino-3,4-dideoxysugars

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Hydrazinreaktionen, I. Fragmentierung von α‐Mesyloxy‐carbonsäurehydraziden. Synthese von 5‐Desoxy‐D‐xylo‐hexofuranuronsäurelacton

Cited by 40 publications

References 13 publications

A New Method for the Synthesis of 2,3-Aziridino-2,3-dideoxyhexonamides and Their Conversion into 3-Amino-2,3-dideoxyhexonic Acids

A New Method for the Synthesis of 2,3-Aziridino-2,3-dideoxyhexonamides and Their Conversion into 3-Amino-2,3-dideoxyhexonic Acids

Regio- and Diastereoselective Allenylation of Aldehydes in Aqueous Media: Total Synthesis of (+)-Goniofufurone1

Synthesis of 3-amino-3,4-dideoxysugars

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Regio- and Diastereoselective Allenylation of Aldehydes in Aqueous Media: Total Synthesis of (+)-Goniofufurone¹