New route to branched-chain amino sugars by application of modified wittig reaction to ketoses

1969 ◽  
Vol 10 (6) ◽  
pp. 397-400 ◽  
Author(s):  
Alex Rosenthal ◽  
Donald A. Baker
Keyword(s):  
Wittig Reaction ◽  
Amino Sugars ◽  
Branched Chain

The synthesis of branched-chain amino sugars from C-methylene sugars: a re-assignment of structure

1975 ◽  
Vol 44 (2) ◽  
pp. C9-C11 ◽  
Author(s):  
John S. Brimacombe ◽  
J. Allen Miller ◽  
U. Zakir
Keyword(s):  
Amino Sugars ◽  
Branched Chain

Synthesis of new branched-chain amino sugars

2003 ◽  
Vol 338 (7) ◽  
pp. 673-680 ◽  
Author(s):  
João R de Freitas Filho ◽  
Rajendra M Srivastava ◽  
Waldenberg J.P da Silva ◽  
Louis Cottier ◽  
Denis Sinou
Keyword(s):  
Amino Sugars ◽  
Branched Chain

Branched-chain 2-deoxy sugars. V. Application of the Wittig reaction to methyl 3,4-O-isopropylidene-β-D-erythro-pentopyranosid-2-ulose and attempted synthesis of nucleosides of 2-deoxy-2-C-methylpentoses

1970 ◽  
Vol 48 (20) ◽  
pp. 3253-3257 ◽  
Author(s):  
Alex Rosenthal ◽  
Matej Sprinzl
Keyword(s):  
Hydrogen Chloride ◽  
Wittig Reaction ◽  
Yield Reduction ◽  
Ruthenium Tetroxide ◽  
Branched Chain ◽  
Deoxy Sugars

Oxidation of methyl 3,4-O-isopropylidene-β-D-arabinopyranoside (1) with ruthenium tetroxide afforded methyl 3,4-O-isopropylidene-β-D-erythro-pentopyranosid-2-ulose (2) in 78% yield. Condensation of methylenetriphenylphosphorane with 2 in the presence of H-butyllithium yielded methyl 3,4-O-isopropylidene-2-deoxy-2-C-methylene-β-D-erytho-pentopyranoside (3) in 55% yield. Reduction of the latter with 10% palladium-on-charcoal gave a 7:1 mixture of two isomeric 2-deoxy-2-C-methylpentoside derivatives in 95% yield: the preponderant product had the D-ribo configuration. The fully blocked methyl glycosides were de-isopropylidenated with methanolic hydrogen chloride to yield 6 and 7 and these were converted into the p-toluoyl esters (8) and (9). Attempts to utilize the latter in the synthesis of nucleosides of 2-deoxy-2-C-methyl pentoses were unsuccessful.

A route to functionalized branched-chain amino sugars via nitrous acid promoted spiroaziridine formation

1988 ◽  
Vol 53 (19) ◽  
pp. 4616-4618 ◽  
Author(s):  
Ricardo Jose Alves ◽  
Sergio Castillon ◽  
Aimee Dessinges ◽  
Pal Herczegh ◽  
J. Cristobal Lopez ◽  
...  
Keyword(s):  
Nitrous Acid ◽  
Amino Sugars ◽  
Branched Chain

An approach to the synthesis of branched-chain amino sugars from C-methylene sugars

1975 ◽  
Vol 41 (1) ◽  
pp. C3-C5 ◽  
Author(s):  
John S. Brimacombe ◽  
J. Allen Miller ◽  
U. Zakir
Keyword(s):  
Amino Sugars ◽  
Branched Chain
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