Document Detail

Convenient preparation of L-arabino-hexos-5-ulose derivatives from lactose.
MedLine Citation:
PMID:  14572719     Owner:  NLM     Status:  MEDLINE    
2,6-di-O-benzyl- (9), 2-O-benzyl-3,4-O-isopropylidene- (19), and 2-O-benzyl-6-O-m-chlorobenzoyl-L-arabino-hexos-5-ulose (20) have been prepared using 4'-deoxy-4'-eno- and 6'-deoxy-5'-eno lactose dimethyl acetal derivatives 7 and 14 as key intermediates. The synthesis of enol ethers 7 and 14 has been performed with good yields by base-promoted elimination of acetone or p-toluenesulfonic acid from 2',6'-di-O-benzyl-, and 6'-O-p-toluenesulfonyl-2,3:5,6:3',4'-tri-O-isopropylidenelactose dimethyl acetal, respectively. The epoxidation with MCPBA of 7 and 14 in methanol or dichloromethane furnishes C-5'-methoxy and C-5'-m-chlorobenzoyloxy derivatives, easily transformed with good yields into L-arabino 5-ketoaldohexoses 9, 19 and 20.
Giorgio Catelani; Antonino Corsaro; Felicia D'Andrea; Manuela Mariani; Venerando Pistarà; Elisa Vittorino
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Carbohydrate research     Volume:  338     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  2003 Oct 
Date Detail:
Created Date:  2003-10-23     Completed Date:  2004-07-02     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  2349-58     Citation Subset:  IM    
Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, I-56126, Pisa, Italy.
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MeSH Terms
Chromatography, Thin Layer
Ketoses / chemical synthesis*,  chemistry*
Lactose / analogs & derivatives,  chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Reg. No./Substance:
0/Ketoses; 26345-59-5/glucosone; 57-15-8/Chlorobutanol; 63-42-3/Lactose

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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