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

Base Information

• Chemical Name: methyl 2-acetamido-3-O-(3,4-di-O-benzyl-6-O-methyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 142466-67-9
• Molecular Formula: C₃₇H₄₇NO₁₁
• Molecular Weight: 681.78
• Mol file: 142466-67-9.mol

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

Chemical Property of methyl 2-acetamido-3-O-(3,4-di-O-benzyl-6-O-methyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-acetamido-3-O-(3,4-di-O-benzyl-6-O-methyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 8 articles about methyl 2-acetamido-3-O-(3,4-di-O-benzyl-6-O-methyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-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: 97.0%

methyl 2-acetamido-3-O-(2-O-acetyl-3,4-di-O-benzyl-6-O-methyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside (142466-66-8) → methyl 2-acetamido-3-O-(3,4-di-O-benzyl-6-O-methyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside (142466-67-9)

Guidance literature:

With sodium methylate; In methanol;

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) → methyl 2-acetamido-3-O-(3,4-di-O-benzyl-6-O-methyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside (142466-67-9)

Guidance literature:

Multi-step reaction with 8 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

6: 76 percent / Hg(CN)2, calcium sulfate , 4 Angstroem molecular sieves / toluene; nitromethane / 2 h / Ambient temperature

7: 72 percent / NaBH₃CN, HCl / tetrahydrofuran

8: 97 percent / NaOMe / methanol

With 2,4,6-trimethyl-pyridine; hydrogenchloride; calcium sulfate; Acetyl bromide; 4 A molecular sieve; tetraethylammonium bromide; hydrogen bromide; sodium methylate; mercury(II) cyanide; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; methanol; nitromethane; dichloromethane; toluene;

Reference yield:

(3aR,5R,6R,7S,7aR)-2-Methoxy-5-methoxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol → methyl 2-acetamido-3-O-(3,4-di-O-benzyl-6-O-methyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside (142466-67-9)

Guidance literature:

Multi-step reaction with 5 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

3: 76 percent / Hg(CN)2, calcium sulfate , 4 Angstroem molecular sieves / toluene; nitromethane / 2 h / Ambient temperature

4: 72 percent / NaBH₃CN, HCl / tetrahydrofuran

5: 97 percent / NaOMe / methanol

With hydrogenchloride; calcium sulfate; Acetyl bromide; 4 A molecular sieve; tetraethylammonium bromide; sodium methylate; mercury(II) cyanide; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; methanol; nitromethane; dichloromethane; toluene;

upstream raw materials:

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

6-O-methyl-α/β-D-galactopyranose

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

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

Downstream raw materials:

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