2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylchloride

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylchloride
• CAS No.: 25320-59-6
• Molecular Formula: C34H35 Cl O5
• Molecular Weight: 559.102
• Mol file: 25320-59-6.mol

Synonyms:Glucopyranosylchloride, 2,3,4,6-tetra-O-benzyl-, a-D- (8CI); 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosyl chloride; Tetra-O-benzyl-a-D-glucopyranosyl chloride

Chemical Property of 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylchloride

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.612
• Boiling Point: 663.284°C at 760 mmHg
• Flash Point: 171.477°C
• PSA: 46.15000
• Density: 1.225g/cm³
• LogP: 6.92310
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

Purity/Quality:

98%min ^*data from raw suppliers

2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Chloro 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranoside (cas# 25320-59-6) is a compound useful in organic synthesis.

Technology Process of 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylchloride

There total 70 articles about 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylchloride 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: 98.0%

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → tetra-O-benzyl glucopyranosyl chloride (25320-59-6)

Guidance literature:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose; With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 0.5h; Inert atmosphere;

In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1039/c8ob02413h

Reference yield: 98.0%

2,3,4,6-tetra-O-benzyl-D-galactopyranose (6386-24-9) → (2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran (4291-68-3,25320-59-6,41110-63-8,67068-83-1,67773-44-8,69237-96-3,92470-93-4,93601-69-5,113829-62-2)

Guidance literature:

With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.3762/bjoc.8.46

Reference yield: 97.0%

2,3,4,6-tetra-O-benzyl-α-D-galactopyranose (4132-28-9,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4291-69-4) → (2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran (4291-68-3,25320-59-6,41110-63-8,67068-83-1,67773-44-8,69237-96-3,92470-93-4,93601-69-5,113829-62-2)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/S0008-6215(82)80005-0

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-glucopyranose

(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triol

Downstream raw materials:

O-ethyl S-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl) dithiocarbonate

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl-(1?1)-2,3,4,6-tetra-O-benzyl-D-glucopyranoside

2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

Refernces

• 1、 Chen, Xi,Ding, Ya-Nan,Gou, Xue-Ya,Liang, Yong-Min,Luan, Yu-Yong,Niu, Zhi-Jie,Shi, Wei-Yu,Zhang, Zhe,Zheng, Nian. "Highly regioselective and stereoselective synthesis of C-Aryl glycosidesvianickel-catalyzedortho-C-H glycosylation of 8-aminoquinoline benzamides". supporting information. p. 8945 - 8948. Retrieved 2021/09/10.
• 2、 Choutka, Jan,Kratochvíl, Michal,Parkan, Kamil,Pohl, Radek,Zyka, Jakub. "Straightforward synthesis of protected 2-hydroxyglycals by chlorination-dehydrochlorination of carbohydrate hemiacetals". supporting information. . Retrieved 2020/08/24.