2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-1-O-methyl-α-D-allopyranoside

Base Information

• Chemical Name: 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-1-O-methyl-α-D-allopyranoside
• CAS No.: 18933-59-0
• Molecular Formula: C₁₄H₁₅BrO₅
• Molecular Weight: 343.174
• Mol file: 18933-59-0.mol

Synonyms:2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-1-O-methyl-α-D-allopyranoside

Chemical Property of 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-1-O-methyl-α-D-allopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-1-O-methyl-α-D-allopyranoside

There total 4 articles about 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-1-O-methyl-α-D-allopyranoside 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: 84.0%

methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside (66537-92-6) → 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-1-O-methyl-α-D-allopyranoside (18933-59-0)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In benzene; at 80 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/anie.201402255

Reference yield: 81.0%

methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside (3150-15-0) → 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-1-O-methyl-α-D-allopyranoside (18933-59-0)

Guidance literature:

With N-Bromosuccinimide; calcium carbonate; In tetrachloromethane; 1,2-dichloro-ethane; for 1h; Heating;

Reference yield:

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-1-O-methyl-α-D-allopyranoside (18933-59-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 96 h / 55 °C / Inert atmosphere

2: sodium methylate / methanol; dichloromethane / 72 h / 0 - 20 °C / Inert atmosphere

3: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / benzene / 0.5 h / 80 °C / Inert atmosphere

With pyridine; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sodium methylate; In methanol; dichloromethane; benzene;

DOI:10.1002/anie.201402255

upstream raw materials:

methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside

methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside

methyl 4,6-di-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside

Downstream raw materials:

methyl 2,3-anhydro-4-O-benzoyl-6-deoxy-6-furfurylthio-α-D-allopyranoside

Benzoic acid (1R,2S,4R,5R,6R)-4-(3-ethoxycarbonyl-but-3-enyl)-2-methoxy-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester

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

methyl 2,3-anhydro-4-O-benzoyl-6-decylsulfonyl-6-deoxy-α-D-allopyranoside