The effect of replacing a 3-O-acetyl group by a 3-O-benzyl group in a methyl 4-O-trityl-β-d-xylopyranoside derivative on the efficiency of 1,2-trans-glycosylation with a d-xylose 1,2-O-(1-cyanoethylidene) derivative

The effect of replacing a 3-O-acetyl group by a 3-O-benzyl group in a methyl 4-O-trityl-β-d-xylopyranoside derivative on the efficiency of 1,2-trans-glycosylation with a d-xylose 1,2-O-(1-cyanoethylidene) derivative Full article

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 1989, Volume: 191, Number: 1, Pages: 13-19 Pages count : 7 DOI: 10.1016/0008-6215(89)85042-6

Authors

Nifant'ev Nikolay E. ¹ , Backinowsky Leon V. ¹ , Kochetkov Nikolay K. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the U.S.S.R., Moscow, U.S.S.R.

Replacement of AcO-3 in methyl 2,3-di-O-acetyl-4-O-trityl-β-d-xylopyranoside with a benzyl group greatly increases the 1,2-trans-stereoselectivity of glycosylation with a d-xylopyranose 1,2-O-(1-cyanoethylidene) derivative. Anomerisation of methyl 2-O-benzyl-β-d-xylopyranoside derivatives occurred under the action of triphenylmethylium perchlorate.

Nifant'ev N.E. , Backinowsky L.V. , Kochetkov N.K.
The effect of replacing a 3-O-acetyl group by a 3-O-benzyl group in a methyl 4-O-trityl-β-d-xylopyranoside derivative on the efficiency of 1,2-trans-glycosylation with a d-xylose 1,2-O-(1-cyanoethylidene) derivative
Carbohydrate Research. 1989. V.191. N1. P.13-19. DOI: 10.1016/0008-6215(89)85042-6 WOS Scopus OpenAlex

≡ Web of science:	WOS:A1989AM14700002
≡ Scopus:	2-s2.0-0039597908
≡ OpenAlex:	W2087444856