75996-21-3

Basic information

• Product Name: methyl-[O²-acetyl-O³-benzoyl-O⁴,O⁶-((R)-benzylidene)-α-D-glucopyranoside]
• CAS NO: 75996-21-3
• Molecular Weight: 428.439
• Mol File: 75996-21-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl-[O²-acetyl-O³-benzoyl-O⁴,O⁶-((R)-benzylidene)-α-D-glucopyranoside](CAS DataBase Reference)
• NIST Chemistry Reference: methyl-[O²-acetyl-O³-benzoyl-O⁴,O⁶-((R)-benzylidene)-α-D-glucopyranoside](75996-21-3)
• EPA Substance Registry System: methyl-[O²-acetyl-O³-benzoyl-O⁴,O⁶-((R)-benzylidene)-α-D-glucopyranoside](75996-21-3)

Safety Data

• Hazardous Substances Data: 75996-21-3(Hazardous Substances Data)

Upstream product

• 2774-23-4 methyl 2-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 98-88-4 benzoyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 33535-04-5 methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 80245-04-1 methyl 3,4,6-tri-O-benzoyl-α-D-glucopyranoside 
• 1313374-91-2 methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-glucopyranoside 
• 1313374-90-1 methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-glucopyranoside 

Relevant articles and documents

Studies on the stereoselective synthesis of a protected α-D-Gal-(1→2)-D-Glc fragment

A novel 1,2-cis stereoselective synthesis of protected α-D-Gal- (1→2)-D-Glc fragments was developed. Methyl 2-O-acetyl-3-O-allyl-4,6-O- benzylidene-α-D-galactopyranosyl-(1→2)-3-O-benzoyl-4, 6-O-benzylidene-α-D-glucopyranoside (13), methyl 2-O-acetyl-3-O-allyl-4,6- O-benzylidene-α-D-galactopyranosyl-(1→2)-3,4,6-tri-O-benzoyl-α- D-glucopyranoside (15), methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-α-D- galactopyranosyl-(1→2)-3-O-benzoyl-4,6-O-benzylidene-β-D- glucopyranoside (17), and methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-α- D-galactopyranosyl-(1→2)-3,4,6-tri-O-benzoyl-β-D-glucopyranoside (19) were favorably obtained by coupling a new donor, isopropyl 2-O-acetyl-3-O-allyl- 4,6-O-benzylidene-1-thio-β-D-galactopyranoside (2), with acceptors, methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside (4), methyl 3,4,6-tri-O-benzoyl-α-D-glucopyranoside (5), methyl 3-O-benzoyl-4,6-O- benzylidene-β-D-glucopyranoside (8), and methyl 3,4,6-tri-O-benzoyl-β- D-glucopyranoside (12), respectively. By virtue of the concerted 1,2-cis α-directing action induced by the 3-O-allyl and 4,6-O-benzylidene groups in donor 2 with a C-2 acetyl group capable of neighboring-group participation, the couplings were achieved with a high degree of α selectivity. In particular, higher α/β stereoselective galactosylation (5.0:1.0) was noted in the case of the coupling of donor 2 with acceptor 12 having a β-CH3 at C-1 and benzoyl groups at C-4 and C-6.