2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl chloride

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl chloride
• CAS No.: 14262-87-4
• Molecular Formula: C₃₄H₂₇ClO₉
• Molecular Weight: 615.036
• Mol file: 14262-87-4.mol

Synonyms:2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl chloride

Chemical Property of 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl chloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl chloride

There total 5 articles about 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl chloride 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: 94.0%

2,3,4,6-tetra-O-benzoyl-α,β-D-mannospyranose (627466-98-2) → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl chloride (14262-87-4)

Guidance literature:

With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/chem.201905576

Reference yield: 88.0%

C40H31NO11 → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl chloride (14262-87-4)

Guidance literature:

With copper dichloride; In dichloromethane; at 20 ℃; Molecular sieve; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00078

Reference yield: 66.0%

D-Mannose (3458-28-4) + benzoyl chloride (98-88-4) → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl chloride (14262-87-4)

Guidance literature:

With indium(III) triflate; at 20 ℃; for 3h;

DOI:10.1080/00397910903419886

upstream raw materials:

1,2,3,4,6-penta-O-benzoyl-β-D-mannopyranose

benzoyl chloride

D-Mannose

2,3,4,6-tetra-O-benzoyl-α,β-D-mannospyranose

Downstream raw materials:

methyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

2,3,4,6-tetra-O-benzoyl-α,β-D-mannospyranose

2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside

Refernces

• 1、 Balzer, Paul G.,Blaszczyk, Stephanie A.,Duan, Xiyan,Ma, Zhi-Xiong,Simmons, Christopher J.,Stevens, Christopher M.,Tang, Weiping,Wang, Hao-Yuan,Wen, Peng,Ye, Wenjing,Yin, Dan. "Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions". supporting information. . Retrieved 2020/02/28.