Reduction of Acylated Aldono-γ-lactones to Aldofuranose Derivatives. A New Synthetic Pathway to Nucleosides

Kohn, Paul M.; Samaritano, Rita H.; Lerner, Léon M.

doi:10.1021/ja01061a054

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2010

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Cited by 13 publications

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“…The distortion is likely to take the form of a flattening of the A ring in order to relieve the C-4-C-10 1,3-diaxial interaction of the two methyl groups. 4 The result of such flattening is an increase in the C-3-C-5 distance.…”

Section: Resultsmentioning

confidence: 99%

The Solvolysis of 4α- and 4α-Methylcholesteryl p-Toluenesulfonates. A Kinetic Study. II^1,2

Sousa¹,

Moriarty²

1965

J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

The Solvolysis of 4α- and 4α-Methylcholesteryl p-Toluenesulfonates. A Kinetic Study. II^1,2

Sousa¹,

Moriarty²

1965

J. Org. Chem.

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Kiliani‐Fischer Cyanohydrin Synthesis

2010

Comprehensive Organic Name Reactions and Reagents

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The conversion of aldose into two one‐carbon‐higher epimeric homologs, which involves a nucleophilic addition of cyanide to the terminal carbonyl group of an aldose, hydrolysis of cyanohydrin, and reduction of the resulting lactone is generally known as the Kiliani–Fischer cyanohydrin synthesis. The study finds that alkaline conditions are required to maintain high effective concentration of cyanide for the performance of the reaction. This reaction is useful for the preparation of higher‐order aldoses and isotope‐labeled carbohydrates.

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Disiamylborane

Ho¹,

Fieser²,

Fieser³

2006

Fieser and Fieser's Reagents for Organic Synthesis

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Reduction of Acylated Aldono-γ-lactones to Aldofuranose Derivatives. A New Synthetic Pathway to Nucleosides

Cited by 13 publications

References 1 publication

The Solvolysis of 4α- and 4α-Methylcholesteryl p-Toluenesulfonates. A Kinetic Study. II^1,2

The Solvolysis of 4α- and 4α-Methylcholesteryl p-Toluenesulfonates. A Kinetic Study. II^1,2

Kiliani‐Fischer Cyanohydrin Synthesis

Disiamylborane

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Reduction of Acylated Aldono-γ-lactones to Aldofuranose Derivatives. A New Synthetic Pathway to Nucleosides

Cited by 13 publications

References 1 publication

The Solvolysis of 4α- and 4α-Methylcholesteryl p-Toluenesulfonates. A Kinetic Study. II1,2

The Solvolysis of 4α- and 4α-Methylcholesteryl p-Toluenesulfonates. A Kinetic Study. II1,2

Kiliani‐Fischer Cyanohydrin Synthesis

Disiamylborane

Contact Info

Product

Resources

About

The Solvolysis of 4α- and 4α-Methylcholesteryl p-Toluenesulfonates. A Kinetic Study. II^1,2

The Solvolysis of 4α- and 4α-Methylcholesteryl p-Toluenesulfonates. A Kinetic Study. II^1,2