methyl (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside

Base Information

• Chemical Name: methyl (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside
• CAS No.: 70144-58-0
• Molecular Formula: C₂₈H₃₆O₁₅
• Molecular Weight: 612.585

Synonyms:methyl (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside

Chemical Property of methyl (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside

Chemical Property:

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Technology Process of methyl (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside

There total 7 articles about methyl (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(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: 83.0%

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5) + 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-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside (70144-58-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1002/ejoc.200500146

Reference yield: 56.0%

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5) + 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-tetra-O-acetyl-D-mannopyranosyl)-(1->2)-4,6-O-benzylidene-α-D-mannopyranoside + methyl (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside (70144-58-0) + methyl (2,3,4,6-tetra-O-acetyl-D-mannopyranosyl)-(1->2)-[2,3,4,6-tetra-O-acetyl-D-mannopyranosyl-(1->3)]-4,6-O-benzylidene-α-D-mannopyranoside

Guidance literature:

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

DOI:10.1002/ejoc.200300651

Reference yield:

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) + acetobromomannose (13242-53-0) → methyl (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside (70144-58-0)

Guidance literature:

With silver trifluoromethanesulfonate; In dichloromethane; at -30 - 20 ℃; regioselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tetlet.2010.01.044

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

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

phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside

acetobromomannose

Downstream raw materials:

C₂₀H₂₈O₁₁

methyl (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside

methyl 3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside

methyl (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-2-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside

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