2-O-acetyl-3,4-di-O-benzyl-6-O-methyl-α-D-galactopyranosyl bromide

Base Information

• Chemical Name: 2-O-acetyl-3,4-di-O-benzyl-6-O-methyl-α-D-galactopyranosyl bromide
• CAS No.: 142466-65-7
• Molecular Formula: C₂₃H₂₇BrO₆
• Molecular Weight: 479.368
• Mol file: 142466-65-7.mol

Synonyms:2-O-acetyl-3,4-di-O-benzyl-6-O-methyl-α-D-galactopyranosyl bromide

Chemical Property of 2-O-acetyl-3,4-di-O-benzyl-6-O-methyl-α-D-galactopyranosyl bromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-acetyl-3,4-di-O-benzyl-6-O-methyl-α-D-galactopyranosyl bromide

There total 5 articles about 2-O-acetyl-3,4-di-O-benzyl-6-O-methyl-α-D-galactopyranosyl bromide 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: 79.0%

3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-6-O-methyl-α-D-galactopyranose (142466-30-6,142466-64-6) → 2-O-acetyl-3,4-di-O-benzyl-6-O-methyl-α-D-galactopyranosyl bromide (142466-65-7)

Guidance literature:

With Acetyl bromide; 4 A molecular sieve; tetraethylammonium bromide; In dichloromethane; for 1h;

Reference yield:

6-O-methyl-α/β-D-galactopyranose (10287-49-7,14199-58-7,24436-14-4,27552-12-1,31505-26-7,31505-27-8,31505-28-9,31505-29-0,87936-86-5,87936-87-6) → 2-O-acetyl-3,4-di-O-benzyl-6-O-methyl-α-D-galactopyranosyl bromide (142466-65-7)

Guidance literature:

Multi-step reaction with 5 steps

1: HBr

2: 58 percent / Et₄NBr, sym-collidine / 24 h / 60 °C

3: NaOMe / methanol

4: 1.) NaH / 1.) DMF, 0 deg c, 1 h, 2.) 0 deg C to r.t., 16 h

5: 79 percent / acetyl bromide, Et₄NBr, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h

With 2,4,6-trimethyl-pyridine; Acetyl bromide; 4 A molecular sieve; tetraethylammonium bromide; hydrogen bromide; sodium methylate; sodium hydride; In methanol; dichloromethane;

Reference yield:

(3aR,5R,6R,7S,7aR)-2-Methoxy-5-methoxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol → 2-O-acetyl-3,4-di-O-benzyl-6-O-methyl-α-D-galactopyranosyl bromide (142466-65-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, 0 deg c, 1 h, 2.) 0 deg C to r.t., 16 h

2: 79 percent / acetyl bromide, Et₄NBr, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h

With Acetyl bromide; 4 A molecular sieve; tetraethylammonium bromide; sodium hydride; In dichloromethane;

upstream raw materials:

3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-6-O-methyl-α-D-galactopyranose

6-O-methyl-α/β-D-galactopyranose

3,4-di-O-acetyl-1,2-O-(1-methoxyethylidene)-6-O-methyl-α-D-galactopyranose

Downstream raw materials:

methyl 2-acetamido-3-O-(2-O-acetyl-3,4-di-O-benzyl-6-O-methyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-di-O-benzyl-2-O-methyl-α-L-fucopyranosyl)-3-O-<3,4-di-O-benzyl-6-O-methyl-2-O-(2-O-benzyl-3,4-di-O-methyl-α-L-fucopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside

methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-di-O-benzyl-2-O-methyl-α-L-fucopyranosyl)-3-O-(2-O-acetyl-3,4-di-O-benzyl-6-O-methyl-β-D-galactopyranosyl)-β-D-glucopyranoside

methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-di-O-benzyl-2-O-methyl-α-L-fucopyranosyl)-3-O-(3,4-di-O-benzyl-6-O-methyl-β-D-galactopyranosyl)-β-D-glucopyranoside