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Treatment of methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D- mannopyranoside (1) with tert-butyldiphenylsilyl chloride in N,N-dimethylformamide afforded methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(2,3,4,6-tetra-O-acetyl -alpha-D- mannopyranosyl)-alpha-D-mannopyranoside (2). Oxidation of 2 with pyridinium chlorochromate, followed by reduction of the carbonyl group, and subsequent O-deacetylation afforded methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-alpha-D-mannopyranosyl- alpha-D- talopyranoside (5). Cleavage of the tert-butyldiphenylsilyl group of 5 with tetrabutylammonium fluoride in oxolane, followed by hydrogenolysis, gave methyl 2-O-alpha-D-mannopyranosyl-alpha-D-talopyranoside (7). O-Deacetylation of 1 gave methyl 3-O-benzyl-2-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside (8). Treatment of 8 with tert-butyldiphenylsilyl chloride afforded a 6,6'-disilyl derivative, which was converted into a 2',3'-O-isopropylidene derivative, and then further oxidized with pyridinium chlorochromate. The resulting diketone was reduced and removal of the protecting groups gave methyl 2-O-alpha-D-talopyranosyl-alpha-D-talopyranoside (15). The structures of both 7 and 15 were established by 13C-n.m.r. spectroscopy.
R K Jain, and
R Dubey, and
S A Abbas, and
K L Matta
September 1986,
Carbohydrate research,
R K Jain, and
R Dubey, and
S A Abbas, and
K L Matta
August 1990,
Carbohydrate research,
R K Jain, and
R Dubey, and
S A Abbas, and
K L Matta
December 1979,
Carbohydrate research,
R K Jain, and
R Dubey, and
S A Abbas, and
K L Matta
July 1995,
Carbohydrate research,
R K Jain, and
R Dubey, and
S A Abbas, and
K L Matta
September 1986,
Carbohydrate research,
R K Jain, and
R Dubey, and
S A Abbas, and
K L Matta
September 1992,
Bioscience, biotechnology, and biochemistry,
R K Jain, and
R Dubey, and
S A Abbas, and
K L Matta
May 1976,
Biochimica et biophysica acta,
R K Jain, and
R Dubey, and
S A Abbas, and
K L Matta
October 1972,
Carbohydrate research,
R K Jain, and
R Dubey, and
S A Abbas, and
K L Matta
April 1987,
Carbohydrate research,
R K Jain, and
R Dubey, and
S A Abbas, and
K L Matta
May 1992,
Carbohydrate research,
