2,3,4,6-TETRA-O-BENZOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE

Base Information

• Chemical Name: 2,3,4,6-TETRA-O-BENZOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE
• CAS No.: 14218-11-2
• Molecular Formula: C34H27BrO9
• Molecular Weight: 659.487
• Hs Code.: 29329990
• Mol file: 14218-11-2.mol

Synonyms:Glucopyranosylbromide, tetrabenzoate (7CI);Glucopyranosyl bromide, tetrabenzoate, a-D- (8CI);a-D-Glucopyranosyl bromide,tetrabenzoate (9CI);2,3,4,6-Tetra-O-benzoyl-a-D-glucopyranosyl bromide;Tetra-O-benzoyl-a-D-glucopyranosyl bromide;

Chemical Property of 2,3,4,6-TETRA-O-BENZOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 128-131 °C(lit.)
• Refractive Index: 1.648
• Boiling Point: 729.919 °C at 760 mmHg
• Flash Point: 395.241 °C
• PSA: 114.43000
• Density: 1.48 g/cm³
• LogP: 5.64000
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly)

Purity/Quality:

98%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,3,4,5-Tetra-O-benzoyl-α-D-glucopyranosyl bromide (CAS# 14218-11-2) is a useful carbohydrate used in the synthesis of steviol glycosides, and glycosyl polyethers.

Technology Process of 2,3,4,6-TETRA-O-BENZOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE

There total 63 articles about 2,3,4,6-TETRA-O-BENZOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE 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: 100.0%

1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside (2592-58-7,3006-48-2,3006-49-3,13526-09-5,14679-57-3,22415-91-4,29884-70-6,41545-55-5,41545-56-6,41569-33-9,96996-90-6,121570-85-2,121570-86-3) → 2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2)

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; at 0 - 20 ℃; for 2h;

Reference yield: 100.0%

1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside (2592-58-7,3006-48-2,3006-49-3,13526-09-5,14679-57-3,22415-91-4,29884-70-6,41545-55-5,41545-56-6,41569-33-9,96996-90-6,121570-85-2,121570-86-3) → 2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide (14218-11-2,14218-30-5,61198-88-7,108438-33-1,108836-02-8,114682-36-9,127305-34-4,151377-77-4)

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; at 0 ℃; for 0.75h;

DOI:10.1021/jo051503w

Reference yield: 97.0%

1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose (22415-91-4) → 2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2)

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/acs.orglett.7b02760

upstream raw materials:

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

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

1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside

Benzoyl bromide

Downstream raw materials:

5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyuridine

C₄₆H₄₆O₁₅

Refernces

• 1、 Pestova,Izmest’ev,Rubtsova,Polukeev,Kutchin. "Synthesis of Thioglycosides with Nitrogen-Containing Heterocyclic Fragments". . p. 1041 - 1044. Retrieved 2018.
• 2、 Guo, Mengbi,Wang, Xin,Wang, Yitong,Hou, Zhuang,Guo, Chun,Gong, Ping. "Facile and efficient access to C1-aminosugar derivatives under mild conditions". . . Retrieved 2022/02/02.
• 3、 Zhang, Zuo-Peng,Zhong, Ye,Han, Zhen-Bin,Zhou, Lin,Su, Hua-Sheng,Wang, Jian,Liu, Yang,Cheng, Mao-Sheng. "Synthesis, molecular docking analysis and biological evaluations of saccharide-modified thiadiazole sulfonamide derivatives". . . Retrieved 2021/05/26.