methyl 2,3-di-O-benzyl-4,6-O-<(R)-(1-ethoxycarbonyl)ethylidene>-α-D-mannopyranoside

Base Information

• Chemical Name: methyl 2,3-di-O-benzyl-4,6-O-<(R)-(1-ethoxycarbonyl)ethylidene>-α-D-mannopyranoside
• CAS No.: 118545-17-8
• Molecular Formula: C₂₆H₃₂O₈
• Molecular Weight: 472.535
• Mol file: 118545-17-8.mol

Synonyms:methyl 2,3-di-O-benzyl-4,6-O-<(R)-(1-ethoxycarbonyl)ethylidene>-α-D-mannopyranoside

Chemical Property of methyl 2,3-di-O-benzyl-4,6-O-<(R)-(1-ethoxycarbonyl)ethylidene>-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3-di-O-benzyl-4,6-O-<(R)-(1-ethoxycarbonyl)ethylidene>-α-D-mannopyranoside

There total 4 articles about methyl 2,3-di-O-benzyl-4,6-O-<(R)-(1-ethoxycarbonyl)ethylidene>-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: 34.0%

2-oxo-propionic acid ethyl ester (617-35-6) + methyl 2,3-di-O-benzyl-4,6-bis-O-(tert-butyldimethylsilyl)-α-D-mannopyranoside (118545-11-2) → methyl 2,3-di-O-benzyl-4,6-O-<(R)-(1-ethoxycarbonyl)ethylidene>-α-D-mannopyranoside (118545-17-8) + methyl 2,3-di-O-benzyl-4,6-O-<(S)-(1-ethoxycarbonyl)ethylidene>-α-D-mannopyranoside (118545-22-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at -5 ℃; for 120h;

DOI:10.1016/0008-6215(88)85070-5

Reference yield:

2-oxo-propionic acid ethyl ester (617-35-6) + methyl 2,3-di-O-benzyl-4,6-bis-O-trimethylsilyl-α-D-mannopyranoside → methyl 2,3-di-O-benzyl-4,6-O-<(R)-(1-ethoxycarbonyl)ethylidene>-α-D-mannopyranoside (118545-17-8) + methyl 2,3-di-O-benzyl-4,6-O-<(S)-(1-ethoxycarbonyl)ethylidene>-α-D-mannopyranoside (118545-22-5) + (R)-4-((2R,3S,4S,5S)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-methyl-[1,3]dioxolane-2-carboxylic acid ethyl ester

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at -5 ℃; for 48h;

DOI:10.1016/S0040-4020(01)89567-3

Reference yield:

methyl 2,3-di-O-benzyl-α-D-mannopyranoside (6988-40-5,17791-36-5,29388-46-3,31873-34-4,33164-03-3,52526-60-0,61117-12-2,87392-25-4,117605-35-3,51842-19-4) → methyl 2,3-di-O-benzyl-4,6-O-<(R)-(1-ethoxycarbonyl)ethylidene>-α-D-mannopyranoside (118545-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / imidazole / dimethylformamide / 24 h

2: 28 percent Spectr_. / TMSOTf / diethyl ether / 120 h / -5 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)89567-3

upstream raw materials:

2-oxo-propionic acid ethyl ester

methyl 2,3-di-O-benzyl-4,6-bis-O-(tert-butyldimethylsilyl)-α-D-mannopyranoside

methyl 2,3-di-O-benzyl-α-D-mannopyranoside