Sodium Borohydride as a Reducing Agent for Sugar Lactones<sup>1</sup>

Wolfrom, M. L.; Wood, Harry B.

doi:10.1021/ja01150a148

Cited by 97 publications

(18 citation statements)

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“…The removal of carbonyl from heated cellulose was attempted using sodium borohydride and a modification of the method reported by Wolfrom and Wood (11). Preheated cellulose (40 mg) was added to 10 ml of water in which 8.0 mg of sodium borohydride had been dissolved.…”

Section: Reduction Using Sodium Borohydridementioning

confidence: 99%

Competitive Reactions in the Thermal Decomposition of Cellulose

Arseneau¹

1971

Can. J. Chem.

246

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Further evidence is presented to show that when cellulose is heated it undergoes two competitive reactions. The actual sequence of these is clarified, being different from that previously postulated. The natures of these reactions are studied, activation energies are determined, and their possible mechanisms are suggested. The thermogram for levoglucosan decomposition is given and briefly discussed.

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Section: Reduction Using Sodium Borohydridementioning

confidence: 99%

Competitive Reactions in the Thermal Decomposition of Cellulose

Arseneau¹

1971

Can. J. Chem.

246

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“…and treated with sodium borohydride (400 mgm.) (1,19). The resulting solution was kept a t room temperature for 12 hr., then it was acidified with acetic acid, cations were removed with Amberlite IR-120 resin, the solution was concentrated to dryness, and boric acid was removed by repeated addition and distillation of methanol.…”

Section: Measurement Of Oxidation Rates In the Ron-catalyzed Reactionmentioning

confidence: 99%

Further Observations on the Lead Tetraacetate Oxidation of Reducing Disaccharides

Charlson¹,

Perlin²

1956

Can. J. Chem.

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Evidence is presented which supports an earlier suggestion that the linkageposition in a reducing disaccharide may be determined readily by lead tetraacetate oxidation. Compounds examined include alclose and Icetose disaccharides and alclobi~~ronic acids. Two types of reaction-one catalyzed by potassium acetate and the other non-catalyzed-are employed jointly to illustrate oxidation patterns \vhich clearly differentiate each position of the biose linlcage. Partial degradation of reducing disaccharides by lead tetraacetate oxidation is illustrated by the preparation of 2-0-01-and 2-O-8-~-glucopyranosyl-~-erythritol and 4-0-8-D-galactopyra~~osyl-D-erythritol. I n turn, 2-O-~-~-gl~~0pyrall0Syl-~-erythritol is degraded to 2-0-8-D-glucopyranosyl-glycerol.

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“…Prior to the reduction of the carboxylate moiety, compound 3DL was subjected to Fischer methanolysis to give methyl (methyl 5-thiomannopyranosid)uronate 4DL in 62%. 4DL: R f = 0.23 (CHCl 3 -MeOH, 9 : 1), 1 4 , which has been occasionally successful in the reduction of sugar esters [18], to give methyl 5-thiomannopyranoside 5DL in 77%. Spectral data of its tetraacetate were consistent with those reported for D-enantiomer [19].…”

Section: Resultsmentioning

confidence: 99%

Syntheses of 5-Thio-D-Mannose from Petrochemicals and a Disaccharide Analog Containing It

Yuasa

Jouyabu

Mitsuhashi

et al. 2008

Research Letters in Organic Chemistry

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Recommended by Robin PoltPer-O-acetyl-5-thio-DL-mannose was synthesized from petrochemicals in six steps and 9% overall yield. It was then derivatized into glycosyl trichloroacetimidate and subjected to glycosidation reaction with a mannosyl acceptor to give a separatable mixture of disaccharides with 5-thio-D-and L-mannosides. This is the first synthesis of an enantiomerically pure 5-thiosugar derivative from racemic chemicals. The D-glycoside was derivatized into methyl (5-thio-α-D-mannopyranosyl)-2-O-α-D-mannopyranoside 6-phosphate as a potential inhibitor of a golgi α-1,2-mannosidase.

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Sodium Borohydride as a Reducing Agent for Sugar Lactones¹

Cited by 97 publications

References 1 publication

Competitive Reactions in the Thermal Decomposition of Cellulose

Competitive Reactions in the Thermal Decomposition of Cellulose

Further Observations on the Lead Tetraacetate Oxidation of Reducing Disaccharides

Syntheses of 5-Thio-D-Mannose from Petrochemicals and a Disaccharide Analog Containing It

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Sodium Borohydride as a Reducing Agent for Sugar Lactones1

Cited by 97 publications

References 1 publication

Competitive Reactions in the Thermal Decomposition of Cellulose

Competitive Reactions in the Thermal Decomposition of Cellulose

Further Observations on the Lead Tetraacetate Oxidation of Reducing Disaccharides

Syntheses of 5-Thio-D-Mannose from Petrochemicals and a Disaccharide Analog Containing It

Contact Info

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Sodium Borohydride as a Reducing Agent for Sugar Lactones¹