methyl O-<(R)-2,3-di-O-benzoyl-4,6-O-(1-methoxycarbonylethylidene)-β-D-galactopyranosyl>-(1-3)-2,4,6-tri-O-benzoyl-β-D-glucopyranoside

Base Information

• Chemical Name: methyl O-<(R)-2,3-di-O-benzoyl-4,6-O-(1-methoxycarbonylethylidene)-β-D-galactopyranosyl>-(1-3)-2,4,6-tri-O-benzoyl-β-D-glucopyranoside
• CAS No.: 138922-04-0
• Molecular Formula: C₅₂H₄₈O₁₈
• Molecular Weight: 960.942
• Mol file: 138922-04-0.mol

Synonyms:

Chemical Property of methyl O-<(R)-2,3-di-O-benzoyl-4,6-O-(1-methoxycarbonylethylidene)-β-D-galactopyranosyl>-(1-3)-2,4,6-tri-O-benzoyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl O-<(R)-2,3-di-O-benzoyl-4,6-O-(1-methoxycarbonylethylidene)-β-D-galactopyranosyl>-(1-3)-2,4,6-tri-O-benzoyl-β-D-glucopyranoside

There total 5 articles about methyl O-<(R)-2,3-di-O-benzoyl-4,6-O-(1-methoxycarbonylethylidene)-β-D-galactopyranosyl>-(1-3)-2,4,6-tri-O-benzoyl-β-D-glucopyranoside 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%

methyl 2,4,6-tri-O-benzoyl-β-D-glucopyranoside (86394-88-9) + 2,3-di-O-benzoyl-4,6-O-<1-(R)-methoxycarbonyl(ethylidene)>-α-D-galactopyranosyl chloride (138857-92-8) → methyl O-<(R)-2,3-di-O-benzoyl-4,6-O-(1-methoxycarbonylethylidene)-β-D-galactopyranosyl>-(1-3)-2,4,6-tri-O-benzoyl-β-D-glucopyranoside (138922-04-0)

Guidance literature:

With 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate; In dichloromethane; for 0.25h; Ambient temperature;

Reference yield:

1,2,3-tri-O-benzoyl-α-D-galactopyranoside (3253-22-3) → methyl O-<(R)-2,3-di-O-benzoyl-4,6-O-(1-methoxycarbonylethylidene)-β-D-galactopyranosyl>-(1-3)-2,4,6-tri-O-benzoyl-β-D-glucopyranoside (138922-04-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 21 percent / NOBF₄ / CH₂Cl₂ / 4 h / -25 °C

2: 64 percent / Cl₂CHOMe / ZnCl₂ / CHCl₃ / 1 h / 60 °C

3: 70 percent / AgOTf, 2,4,6-trimethylpyridine / CH₂Cl₂ / 0.25 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; Dichloromethyl methyl ether; silver trifluoromethanesulfonate; nitrosonium tetrafluoroborate; zinc(II) chloride; In dichloromethane; chloroform;

Reference yield:

C27H38O8Si2 (138857-61-1) → methyl O-<(R)-2,3-di-O-benzoyl-4,6-O-(1-methoxycarbonylethylidene)-β-D-galactopyranosyl>-(1-3)-2,4,6-tri-O-benzoyl-β-D-glucopyranoside (138922-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) Cl₂CHOMe / 1.) TMSOTf, 2.) ZnCl₂ / 1.) CH₂Cl₂, a) -20 deg C, b) room temperature, 16 h, 2.) CHCl₃, 65 deg C, 13 h

2: 70 percent / AgOTf, 2,4,6-trimethylpyridine / CH₂Cl₂ / 0.25 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; Dichloromethyl methyl ether; silver trifluoromethanesulfonate; trimethylsilyl trifluoromethanesulfonate; zinc(II) chloride; In dichloromethane;

upstream raw materials:

methyl 2,4,6-tri-O-benzoyl-β-D-glucopyranoside

2,3-di-O-benzoyl-4,6-O-<1-(R)-methoxycarbonyl(ethylidene)>-α-D-galactopyranosyl chloride

1,2,3-tri-O-benzoyl-α-D-galactopyranoside

C₂₇H₃₈O₈Si₂