Elsevier
Carbohydrate Research
,  volume 152 ,  pages 195-203

Synthesis of methyl 2-O- and 3-O-α-d-talopyranosyl-α-d-mannopyranoside

Surjit S Rana 1
, 
Khushi L. Matta 1
1
 
Department of Gynecologic Oncology, Roswell Park Memorial Institute, New York State Department of Health, Buffalo, New York 14263, U.S.A. | 
Publication type: Journal Article
Publication date: 1986-09-01
Elsevier
scimago Q3
wos Q2
SJR: 0.423
CiteScore: 4.0
Impact factor: 2.5
ISSN: 00086215, 1873426X
Organic Chemistry
Biochemistry
General Medicine
Analytical Chemistry
Abstract
Methyl 3,4,6-tri-O-benzyl-2-O-[6-O-(tert-butyldiphenylsilyl)-alpha-D- mannopyranosyl]-alpha-D-mannopyranoside (2) was synthesized by treatment of methyl 3,4,6-tri-O-benzyl-2-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside with tert-butylchlorodiphenylsilane in the presence of imidazole. Isopropylidenation, followed by oxidation with pyridinium chlorochromate, and stereoselective reduction with sodium borohydride, converted 2 into methyl 3,4,6-tri-O-benzyl-2-O-[6-O-(tert-butyldiphenylsilyl)-2,3-O-isopro pylidene- alpha-D-talopyranosyl]-alpha-D-mannopyranoside (5). Treatment of 5 with a molar solution of tetrabutylammonium fluoride in dry oxolane produced a diol which, on O-de-isopropylidenation followed by catalytic hydrogenolysis, afforded the disaccharide glycoside methyl 2-O-alpha-D-talopyranosyl-alpha-D-mannopyranoside. Synthesis of methyl 3-O-alpha-D-talopyranosyl-alpha-D-mannopyranoside was accomplished by a similar reaction-sequence. The structures of the final disaccharides, and of various other intermediates, were established by 1H- and 13C-n.m.r. spectroscopy.
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Rana S. S., Matta K. L. Synthesis of methyl 2-O- and 3-O-α-d-talopyranosyl-α-d-mannopyranoside // Carbohydrate Research. 1986. Vol. 152. pp. 195-203.
GOST all authors (up to 50) Copy
Rana S. S., Matta K. L. Synthesis of methyl 2-O- and 3-O-α-d-talopyranosyl-α-d-mannopyranoside // Carbohydrate Research. 1986. Vol. 152. pp. 195-203.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/s0008-6215(00)90299-4
UR - https://doi.org/10.1016/s0008-6215(00)90299-4
TI - Synthesis of methyl 2-O- and 3-O-α-d-talopyranosyl-α-d-mannopyranoside
T2 - Carbohydrate Research
AU - Rana, Surjit S
AU - Matta, Khushi L.
PY - 1986
DA - 1986/09/01
PB - Elsevier
SP - 195-203
VL - 152
PMID - 3768907
SN - 0008-6215
SN - 1873-426X
ER -
BibTex
Cite this
BibTex (up to 50 authors) Copy
@article{1986_Rana,
author = {Surjit S Rana and Khushi L. Matta},
title = {Synthesis of methyl 2-O- and 3-O-α-d-talopyranosyl-α-d-mannopyranoside},
journal = {Carbohydrate Research},
year = {1986},
volume = {152},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016/s0008-6215(00)90299-4},
pages = {195--203},
doi = {10.1016/s0008-6215(00)90299-4}
}