phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-1-thio-β-D-glucopyranoside
• CAS No.: 904319-28-4
• Molecular Formula: C₂₈H₂₇ClO₆S
• Molecular Weight: 527.038
• Mol file: 904319-28-4.mol

Synonyms:phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-1-thio-β-D-glucopyranoside

There total 4 articles about phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-1-thio-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: 96.0%

phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside (128848-51-1) + chloroacetyl chloride (79-04-9) → phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-1-thio-β-D-glucopyranoside (904319-28-4)

Guidance literature:

In pyridine; dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/j.carres.2006.04.019

Reference yield: 92.0%

C26H26O5S + chloroacetyl chloride (79-04-9) → phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-1-thio-β-D-glucopyranoside (904319-28-4)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.9b04264

Reference yield:

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (71676-30-7,87508-18-7,138922-03-9,87508-17-6) → phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-chloroacetyl-1-thio-β-D-glucopyranoside (904319-28-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-Bu₂SnO / benzene / 5 h / Heating

1.2: 84 percent / n-Bu₄NBr / toluene / 5 h / 60 °C

2.1: 96 percent / CH₂Cl₂; pyridine / 2 h / 0 °C

With di(n-butyl)tin oxide; In pyridine; dichloromethane; benzene;

DOI:10.1016/j.carres.2006.04.019

upstream raw materials:

phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

chloroacetyl chloride

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

benzyl bromide

Downstream raw materials:

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-O-benzoyl-3-O-benzyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-benzyl-β-D-glucopyranoside

benzoic acid 6-benzyloxymethyl-5-(8-benzyloxy-2-phenyl-7-trifluoromethanesulfonyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4-(4-methoxy-benzyloxy)-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-O-benzoyl-3-O-benzyl-β-D-mannopyranosyl-(1->4)-2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzyl-β-D-glucopyranoside

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-3-O-benzyl-β-D-glucopyranosyl-(1->4)-2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzoyl-β-D-glucopyranoside