Synthesis of All Diastereomers of the 2-Deoxypentoses and the 2,6-Dideoxyhexoses from 2-Phenyl-1,3-dioxan-5-one Hydrate

All diastereomers of the 2‐deoxypentoses and the 2,6‐dideoxyhexoses were synthesized from 2‐phenyl‐1,3‐dioxan‐5‐one hydrate (1), by alkylation via the RAMP‐hydrazone (2). Some of the diastereomers were synthesized in the racemic form via the dimethylhydrazone (28). The 2‐deoxypentoses were synthesiz...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2001; no. 17; pp. 3367 - 3374
Main Authors Ulven, Trond, Carlsen, Per H. J.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 01.09.2001
WILEY‐VCH Verlag GmbH
Wiley
Subjects
Alkylations
Asymmetric synthesis
Carbohydrates
Chemistry
Chemistry, Organic
Diastereoselectivity
Hydrazones
Physical Sciences
Science & Technology
carbohydrates
BOIVINOSE
asymmetric synthesis
diastereoselectivity
alkylations
hydrazones
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Summary:All diastereomers of the 2‐deoxypentoses and the 2,6‐dideoxyhexoses were synthesized from 2‐phenyl‐1,3‐dioxan‐5‐one hydrate (1), by alkylation via the RAMP‐hydrazone (2). Some of the diastereomers were synthesized in the racemic form via the dimethylhydrazone (28). The 2‐deoxypentoses were synthesized by alkylation with allyl bromide, followed by stereoselective reduction, ozonolysis, and deprotection. The 2,6‐dideoxypentoses were synthesized by dialkylation with allyl bromide and methyl iodide.
Bibliography:ArticleID:EJOC3367
ark:/67375/WNG-TV1FZD8B-R
istex:A72798A6DFFB2881F0618D820580387D9E5C8C71
ISSN:1434-193X
1099-0690
DOI:10.1002/1099-0690(200109)2001:17<3367::AID-EJOC3367>3.0.CO;2-H