allyl 3-O-benzyl-4,6-O-benzylidene-2-C-dichloromethyl-α-D-glucopyranoside

Base Information

• Chemical Name: allyl 3-O-benzyl-4,6-O-benzylidene-2-C-dichloromethyl-α-D-glucopyranoside
• CAS No.: 344615-42-5
• Molecular Formula: C₂₄H₂₆Cl₂O₆
• Molecular Weight: 481.373
• Mol file: 344615-42-5.mol

Synonyms:allyl 3-O-benzyl-4,6-O-benzylidene-2-C-dichloromethyl-α-D-glucopyranoside

Chemical Property of allyl 3-O-benzyl-4,6-O-benzylidene-2-C-dichloromethyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 3-O-benzyl-4,6-O-benzylidene-2-C-dichloromethyl-α-D-glucopyranoside

There total 3 articles about allyl 3-O-benzyl-4,6-O-benzylidene-2-C-dichloromethyl-α-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: 80.0%

dichloromethane (75-09-2) + allyl 3-O-benzyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose (228565-56-8) → allyl 3-O-benzyl-4,6-O-benzylidene-2-C-dichloromethyl-α-D-glucopyranoside (344615-42-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4020(02)01058-X

Reference yield: 70.0%

(dichloromethyl)lithium (2146-67-0) + allyl 3-O-benzyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose (228565-56-8) → allyl 3-O-benzyl-4,6-O-benzylidene-2-C-dichloromethyl-α-D-glucopyranoside (344615-42-5)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4039(01)00246-5

Reference yield:

allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside (128241-14-5) → allyl 3-O-benzyl-4,6-O-benzylidene-2-C-dichloromethyl-α-D-glucopyranoside (344615-42-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

2: 80 percent / BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1: Swern oxidation;

DOI:10.1016/S0040-4020(02)01058-X

upstream raw materials:

(dichloromethyl)lithium

allyl 3-O-benzyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose

dichloromethane

allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside

Downstream raw materials:

allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-formyl-α-D-mannopyranoside

(2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-4-(p-methoxybenzyloxy)-5-[2-(trimethylsilyl)ethoxymethoxy]hexanoamide

allyl 2-azido-3-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-C-(tert-butyldiphenylsilyloxymethyl)-2-deoxy-4-O-(p-methoxybenzyl)-α-D-mannopyranoside

(2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-4-(p-methoxybenzyloxy)hexanoamide