methyl-4-benzoyl-3-O-methyl-6-bromo-2,6-dideoxy-α-D-glucopyranoside

Base Information

• Chemical Name: methyl-4-benzoyl-3-O-methyl-6-bromo-2,6-dideoxy-α-D-glucopyranoside
• CAS No.: 18933-65-8
• Molecular Formula: C₁₅H₁₉BrO₅
• Molecular Weight: 359.217
• Mol file: 18933-65-8.mol

Synonyms:methyl-4-benzoyl-3-O-methyl-6-bromo-2,6-dideoxy-α-D-glucopyranoside

Chemical Property of methyl-4-benzoyl-3-O-methyl-6-bromo-2,6-dideoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-4-benzoyl-3-O-methyl-6-bromo-2,6-dideoxy-α-D-glucopyranoside

There total 9 articles about methyl-4-benzoyl-3-O-methyl-6-bromo-2,6-dideoxy-α-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: 71.0%

4,6-O-Benzylidene-2-deoxy-3-O-methyl-α-D-arabino-hexopyranoside (126373-46-4) → methyl-4-benzoyl-3-O-methyl-6-bromo-2,6-dideoxy-α-D-glucopyranoside (18933-65-8)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); barium carbonate; In tetrachloromethane; for 2h;

DOI:10.1016/j.bmcl.2017.06.008

Reference yield:

methyl-[O4,O6-((R)-benzylidene)-O3-methyl-α-D-ribo-2-deoxy-hexopyranoside] (21090-92-6,53131-18-3,66537-93-7,126373-46-4,135818-56-3,138663-50-0) → Methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-3-O-methyl-α-D-ribo-hexopyranoside (18933-65-8,67909-11-9,135708-66-6,61653-42-7)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); barium carbonate; In tetrachloromethane; for 1h; Inert atmosphere; Reflux;

DOI:10.1039/c2cc34404a

Reference yield:

methyl 2-deoxy-4,6-O-benzylidene-α-D-ribo-hexopyranoside (6752-48-3,16718-95-9,18424-62-9,19877-02-2,22886-97-1,52153-29-4,52612-68-7,55331-65-2,64978-95-6,65725-24-8,66512-93-4,67968-51-8,72904-80-4,77481-69-7,131615-73-1,138663-49-7,151214-39-0) → Methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-3-O-methyl-α-D-ribo-hexopyranoside (18933-65-8,67909-11-9,135708-66-6,61653-42-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / tetrahydrofuran / 4.5 h / Cooling; Inert atmosphere

2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); barium carbonate / tetrachloromethane / 1 h / Inert atmosphere; Reflux

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sodium hydride; barium carbonate; In tetrahydrofuran; tetrachloromethane;

DOI:10.1039/c2cc34404a

upstream raw materials:

methyl 2-deoxy-4,6-O-benzylidene-α-D-ribo-hexopyranoside

methyl-[O⁴,O⁶-((R)-benzylidene)-O³-methyl-α-D-ribo-2-deoxy-hexopyranoside]

methyl 4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose

Downstream raw materials:

4-O-acetyl-D-cymaropyranosyl ortho-hexynylbenzoate

methyl 4-O-(2,4-di-O-benzoyl-D-thevetopyranosyl)-β-D-cymaropyranoside

methyl 4-O-(2,4-di-O-benzoyl-D-thevetopyranosyl)-α-D-cymaropyranoside

methyl 2,6-dideoxy-3-O-methyl-α-D-ribo-hexopyranoside