methyl 4,6-O-benzylidene-3-O-benzyl-2-O-(methoxycarbonylmethyl)-α-D-mannopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-3-O-benzyl-2-O-(methoxycarbonylmethyl)-α-D-mannopyranoside
• CAS No.: 136632-92-3
• Molecular Formula: C₂₄H₂₈O₈
• Molecular Weight: 444.482
• Mol file: 136632-92-3.mol

Synonyms:methyl 4,6-O-benzylidene-3-O-benzyl-2-O-(methoxycarbonylmethyl)-α-D-mannopyranoside

Chemical Property of methyl 4,6-O-benzylidene-3-O-benzyl-2-O-(methoxycarbonylmethyl)-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-O-benzylidene-3-O-benzyl-2-O-(methoxycarbonylmethyl)-α-D-mannopyranoside

There total 3 articles about methyl 4,6-O-benzylidene-3-O-benzyl-2-O-(methoxycarbonylmethyl)-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:

benzyl bromide (100-39-0) → methyl 4,6-O-benzylidene-3-O-benzyl-2-O-(methoxycarbonylmethyl)-α-D-mannopyranoside (136632-92-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) dibutyltin oxide / 1) MeOH, 60 deg C, 1 h, 2) N,N-dimethylformamide, 100 deg C, 25 min

2: 1) NaH, imidazole, Bu₄NBr / 1) THF, reflux, 0.5 h, 2) reflux, overnight

With 1H-imidazole; tetrabutylammomium bromide; sodium hydride; di(n-butyl)tin oxide;

DOI:10.1016/0008-6215(91)84134-Z

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) → methyl 4,6-O-benzylidene-3-O-benzyl-2-O-(methoxycarbonylmethyl)-α-D-mannopyranoside (136632-92-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) dibutyltin oxide / 1) MeOH, 60 deg C, 1 h, 2) N,N-dimethylformamide, 100 deg C, 25 min

2: 1) NaH, imidazole, Bu₄NBr / 1) THF, reflux, 0.5 h, 2) reflux, overnight

With 1H-imidazole; tetrabutylammomium bromide; sodium hydride; di(n-butyl)tin oxide;

DOI:10.1016/0008-6215(91)84134-Z

Reference yield:

(2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (2774-19-8,14419-69-3,15887-67-9,23392-28-1,57539-08-9,61277-63-2,74410-51-8,76419-48-2,80734-73-2,86363-44-2,89301-79-1,94061-92-4,94062-87-0,108739-92-0,129706-93-0,143005-12-3,65877-21-6) + bromoacetic acid methyl ester (96-32-2) → methyl 4,6-O-benzylidene-3-O-benzyl-2-O-(methoxycarbonylmethyl)-α-D-mannopyranoside (136632-92-3)

Guidance literature:

With 1H-imidazole; tetrabutylammomium bromide; sodium hydride; Yield given. Multistep reaction; 1) THF, reflux, 0.5 h, 2) reflux, overnight;

DOI:10.1016/0008-6215(91)84134-Z

upstream raw materials:

(2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

bromoacetic acid methyl ester

benzyl bromide

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

Downstream raw materials:

methyl 4,6-O-benzylidene-3-O-benzyl-2-O-(2-hydroxyethyl)-α-D-mannopyranoside