METHYL-2,3,4-TRI-O-ACETYL-6-BROMO-6-DEOXY-ALPHA-D-GLUCOPYRANOSIDE

Base Information

• Chemical Name: METHYL-2,3,4-TRI-O-ACETYL-6-BROMO-6-DEOXY-ALPHA-D-GLUCOPYRANOSIDE
• CAS No.: 7404-32-2
• Molecular Formula: C13H19BrO8
• Molecular Weight: 383.193
• Mol file: 7404-32-2.mol

Synonyms:Glucopyranoside,methyl 6-bromo-6-deoxy-, triacetate, a-D- (8CI);α-D-Glucopyranoside, methyl 6-bromo-6-deoxy-,triacetate (9CI);Methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-a-D-glucopyranoside;NSC 403466;

Chemical Property of METHYL-2,3,4-TRI-O-ACETYL-6-BROMO-6-DEOXY-ALPHA-D-GLUCOPYRANOSIDE

Chemical Property:

• Vapor Pressure: 1.62E-06mmHg at 25°C
• Refractive Index: 1.496
• Boiling Point: 397.2 °C at 760 mmHg
• Flash Point: 194 °C
• PSA: 97.36000
• Density: 1.158 g/cm³
• LogP: 0.54770

Purity/Quality:

99% ^*data from raw suppliers

METHYL-2,3,4-TRI-O-ACETYL-6-BROMO-6-DEOXY-ALPHA-D-GLUCOPYRANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of METHYL-2,3,4-TRI-O-ACETYL-6-BROMO-6-DEOXY-ALPHA-D-GLUCOPYRANOSIDE

There total 7 articles about METHYL-2,3,4-TRI-O-ACETYL-6-BROMO-6-DEOXY-ALPHA-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: 77.0%

acetic anhydride (108-24-7) + methyl 6-bromo-6-deoxy-α-D-glucopyranoside (7465-44-3) → methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranoside (7404-32-2)

Guidance literature:

With pyridine; for 24h; Ambient temperature;

Reference yield:

methyl-alpha-D-glucopyranoside (97-30-3) → methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranoside (7404-32-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) methanesulfonyl bromide, 2.) sodium methoxide / 1.) DMF, 65 deg C, 19 h, 2.) MeOH

2: 77 percent / pyridine / 24 h / Ambient temperature

With pyridine; methanesulfonyl bromide; sodium methylate;

Reference yield:

methyl-alpha-D-glucopyranoside (97-30-3) → methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranoside (7404-32-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutylammomium bromide; (chloro-phenylthio-methylene)dimethylammonium chloride / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere

2: pyridine

With pyridine; tetrabutylammomium bromide; (chloro-phenylthio-methylene)dimethylammonium chloride; In N,N-dimethyl-formamide;

DOI:10.1002/cjoc.201200211

upstream raw materials:

methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-L-idopyranoside

acetic anhydride

methyl 6-bromo-6-deoxy-α-D-glucopyranoside

methyl-alpha-D-glucopyranoside

Downstream raw materials:

methyl 6-bromo-6-deoxy-α-D-glucopyranoside

methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-L-idopyranoside

methyl 2,3,4-tri-O-acetyl-6-deoxy-6-phenylthio-α-D-glucopyranoside

methyl 2,3,4-tri-O-acetyl-6-deoxy-6-phenylseleno-α-D-glucopyranoside

Refernces

• 1、 Berberan-Santos, Mário N.,Canceill, Josette,Brochon, Jean-Claude,Jullien, Ludovic,Lehn, Jean-Marie,Pouget, Jacques,Tauc, Patrick,Valeur, Bernard. "Multichromophoric Cyclodextrins. 1. Synthesis of O-Naphthoyl-β-cyclodextrins and Investigation of Excimer Formation and Energy Hopping". . p. 6427 - 6436. Retrieved 2007/10/02.