Journal
CARBOHYDRATE RESEARCH
Volume 341, Issue 16, Pages 2658-2668Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2006.08.009
Keywords
enol acetates; aldehydo-suggars; aldehydrol diacetates; photoisomerization; aldehydrols
Funding
- NIGMS NIH HHS [GM11976] Funding Source: Medline
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Acetylation of the 2,3-O-isopropylidene derivative (1) of D-glyceraldehyde with hot acetic anhydride in the presence of sodium acetate give a mixture of (Z)- and (E)-enol acetates (2 and 3). together with the acetylated racemic aldehydrol (4) of 1. Likewise, the acyclic aldehydo 2,3:4,5-diisopropylidene acetals of D- and L-arabinose, D-xylose, and D-ribose underwent conversion into enol acetates, with the (Z) isomers preponderating, and convertible photochernically into the corresponding (E) isomers. Under other conditions of acetylation.. the aldehydo derivatives were converted into the corresponding aldehydrol diacetates. (c) 2006 Elsevier Ltd. All rights reserved.
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