182187-95-7

Upstream product

• 530-26-7 D-Mannose 
• 41308-76-3 allyl α-D-mannopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 1055301-32-0 allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside 
• 1055301-36-4 allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->4)-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside 
• 1055301-34-2 allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside 
• 1055301-74-0 allyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside 

Relevant academic research and scientific papers

Total Synthesis of 6-Amino-2,6-dideoxy-α-Kdo from d -Mannose

3-Deoxy-d-manno-oct-2-ulosonic acid (Kdo) biosynthetic pathway is a promising target in antibacterial drug discovery. Herein, we report the total synthesis of 6-amino-2,6-dideoxy-α-Kdo in 15 steps from d-mannose as a potential inhibitor of Kdo-processing

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.