88713-99-9

Upstream product

• 88713-96-6 methyl 4,6-di-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-α-D-mannopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 63167-69-1 methyl 2,3-O-isopropylidene-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 182187-84-4 (2R,3R,4S,5S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,5-diol 

Downstream Products

• 88714-03-8 methyl 4,6-di-O-(tert-butyldiphenylsilyl)-2,3-di-O-(trimethylsilyl)-α-D-mannopyranoside 
• 182187-88-8 (2R,3R,4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4,5,6-trimethoxy-tetrahydro-pyran 

Relevant academic research and scientific papers

An efficient approach to partially O-methylated α-D-mannopyranosides using bis-tert-butyldiphenylsilyl ethers as intermediates

Differential migratory aptitudes of secondary tert-butyldiphenylsilyl (DBDPS) groups have been observed for the bis-silylated derivatives of methyl and allyl α-D-mannopyranosides under several basic media. A remarkable variation of the selectivity in the migration of the TBDPS group at position 3 (O-3 → O-2 versus O-3 → O-4) was found by changing the hardness of the base and reaction conditions. This behaviour was directed towards the practical synthesis of the 3,6-, 2,6- and 4,6-bis-TBDPS ethers, 3-5a,b, versatile intermediates for the preparation of other O-substituted derivatives. Their conversion into the methyl and allyl 2,4-, 3,4- and 2,3-di-O-methyl α-D-mannopyranosides (10-12a,b) was successfully achieved.

SYNTHESIS OF METHYL 2,3-O-D-GLYCOPYRANOSYLIDENE α-D-MANNOPYRANOSIDES HAVING VARIOUS SUBSTITUENTS

The title compounds were obtained by condensation of D-glucono-, D-galactono-, or L-glycero-D-gluco-heptono-1,5-lactones with methyl 2,3-di-O-(trimethylsilyl)-α-D-mannopyranosides having various substituents on C-4 and C-6, in the presence of trimethylsil