methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside

Base Information

• Chemical Name: methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside
• CAS No.: 83497-33-0
• Molecular Formula: C₁₄H₁₇BrO₅
• Molecular Weight: 345.19
• Mol file: 83497-33-0.mol

Synonyms:methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside

Chemical Property of methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside

There total 5 articles about methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside 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: 95.0%

methyl 4,6-O-benzylidene-2-deoxy-α-D-altropyranoside (16718-95-9) → methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside (83497-33-0)

Guidance literature:

With N-Bromosuccinimide; barium carbonate; In tetrachloromethane;

DOI:10.1016/S0008-6215(00)80745-4

Reference yield: 65.0%

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-α-D-ribo-hexopyranoside (83497-33-0)

Guidance literature:

With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; at 73 ℃; for 2.6h;

DOI:10.1021/ja0685250

Reference yield:

methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose (63598-31-2) → methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside (83497-33-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / NaBH₄ / tetrahydrofuran; methanol / 1.5 h / 0 - 20 °C

2: 65 percent / N-bromosuccinimide; BaCO₃ / CCl₄ / 2.6 h / 73 °C

With sodium tetrahydroborate; N-Bromosuccinimide; barium carbonate; In tetrahydrofuran; methanol; tetrachloromethane;

DOI:10.1021/ja0685250

upstream raw materials:

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

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

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

benzaldehyde

Downstream raw materials:

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

(2R,3S,4S,6S)-4-hydroxy-6-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate

Benzoic acid (2S,3S,4S,6S)-2-bromomethyl-6-methoxy-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

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