methyl (3S)-<3-(2)H>-2,4-di-O-benzoyl-6-bromo-3,6-dideoxy-α-D-ribo-hexopyranoside

Base Information

• Chemical Name: methyl (3S)-<3-(2)H>-2,4-di-O-benzoyl-6-bromo-3,6-dideoxy-α-D-ribo-hexopyranoside
• CAS No.: 127244-73-9
• Molecular Formula: C₂₁H₂₁BrO₆
• Molecular Weight: 450.29
• Mol file: 127244-73-9.mol

Synonyms:methyl (3S)-<3-(2)H>-2,4-di-O-benzoyl-6-bromo-3,6-dideoxy-α-D-ribo-hexopyranoside

Chemical Property of methyl (3S)-<3-(2)H>-2,4-di-O-benzoyl-6-bromo-3,6-dideoxy-α-D-ribo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3S)-<3-(2)H>-2,4-di-O-benzoyl-6-bromo-3,6-dideoxy-α-D-ribo-hexopyranoside

There total 4 articles about methyl (3S)-<3-(2)H>-2,4-di-O-benzoyl-6-bromo-3,6-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: 57.0%

methyl (3S)-<3-(2)H>-2-O-benzoyl-4,6-O-benzylidene-3-deoxy-α-D-ribo-hexopyranoside (127244-72-8) → methyl (3S)-<3-(2)H>-2,4-di-O-benzoyl-6-bromo-3,6-dideoxy-α-D-ribo-hexopyranoside (127244-73-9)

Guidance literature:

With N-Bromosuccinimide; barium carbonate; dibenzoyl peroxide; In tetrachloromethane; Heating;

DOI:10.1016/S0040-4039(00)76182-X

Reference yield:

methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside (3150-15-0) → methyl (3S)-<3-(2)H>-2,4-di-O-benzoyl-6-bromo-3,6-dideoxy-α-D-ribo-hexopyranoside (127244-73-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / MeI, Mg / tetrahydrofuran / Heating

2: Et₃N / DMAP / CH₂Cl₂

3: 94 percent / NaBD₄, NiCl₂*6H₂O / ethanol

4: 57 percent / NBS, BaCO₃ / benzoyl peroxide / CCl₄ / Heating

With N-Bromosuccinimide; sodium borodeuteride; magnesium; triethylamine; barium carbonate; nickel dichloride; methyl iodide; dmap; dibenzoyl peroxide; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)76182-X

Reference yield:

methyl 4,6-O-benzylidene-3-deoxy-3-iodo-α-D-glucopyranoside (90503-12-1) → methyl (3S)-<3-(2)H>-2,4-di-O-benzoyl-6-bromo-3,6-dideoxy-α-D-ribo-hexopyranoside (127244-73-9)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / DMAP / CH₂Cl₂

2: 94 percent / NaBD₄, NiCl₂*6H₂O / ethanol

3: 57 percent / NBS, BaCO₃ / benzoyl peroxide / CCl₄ / Heating

With N-Bromosuccinimide; sodium borodeuteride; triethylamine; barium carbonate; nickel dichloride; dmap; dibenzoyl peroxide; In tetrachloromethane; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)76182-X

upstream raw materials:

methyl (3S)-<3-(2)H>-2-O-benzoyl-4,6-O-benzylidene-3-deoxy-α-D-ribo-hexopyranoside

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

methyl 4,6-O-benzylidene-3-deoxy-3-iodo-α-D-glucopyranoside

methyl 2-O-benzoyl-4,6-O-benzylidene-3-deoxy-3-iodo-α-D-glucopyranoside

Downstream raw materials:

methyl (3S)-<3-(2)H>-2,4-di-O-benzoyl-3,6-dideoxy-α-D-ribo-hexopyranoside