methyl (2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside

Base Information

• Chemical Name: methyl (2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside
• CAS No.: 688014-95-1
• Molecular Formula: C₃₁H₄₀O₁₇
• Molecular Weight: 684.648
• Mol file: 688014-95-1.mol

Synonyms:methyl (2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside

Chemical Property of methyl (2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside

There total 1 articles about methyl (2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl trichloroacetimidate (135296-88-7) + methyl-4,6-O-phenylmethylene-α-D-mannopyranoside (3162-96-7,4148-58-7,4153-17-7,4288-93-1,5328-47-2,6988-39-2,13566-32-0,14155-23-8,27994-50-9,37093-57-5,37093-59-7,57701-27-6,59168-66-0,64552-06-3,65391-13-1,65391-14-2,65530-26-9,66512-65-0,71117-36-7,71117-37-8,71117-41-4,72904-85-9,74560-56-8,79549-74-9,86783-81-5,96093-51-5,98633-13-7,110415-35-5,110415-36-6,110850-29-8,124020-29-7,126924-12-7,129263-21-4,131433-03-9,145920-49-6,146863-04-9) → methyl (2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside (688014-95-1)

Guidance literature:

With 4 Angstroem MS; boron trifluoride diethyl etherate; In dichloromethane; at -10 ℃; for 2h;

DOI:10.1002/ejoc.200300651

Reference yield: 89.0%

acetic anhydride (108-24-7) + methyl (2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside (688014-95-1) → methyl (2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-(1->3)-2-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside (688014-96-2)

Guidance literature:

With dmap; In pyridine; for 16h;

DOI:10.1002/ejoc.200300651

Reference yield:

methyl (2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside (688014-95-1) → methyl (2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside (688014-98-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / 4-dimethylaminopyridine / pyridine / 16 h

2: 88 percent / AcOH; water / 4 h / 70 °C

3: 87 percent / imidazole / dimethylformamide / 20 h / 20 °C

With 1H-imidazole; dmap; water; acetic acid; In pyridine; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200300651

upstream raw materials:

2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl trichloroacetimidate

methyl-4,6-O-phenylmethylene-α-D-mannopyranoside

Downstream raw materials:

methyl (2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-(1->3)-2-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside

methyl (2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside