methyl 4-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside

Base Information

• Chemical Name: methyl 4-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside
• CAS No.: 109914-58-1
• Molecular Formula: C₁₆H₂₁N₃O₆
• Molecular Weight: 351.359
• Mol file: 109914-58-1.mol

Synonyms:methyl 4-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside

Chemical Property of methyl 4-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside

There total 10 articles about methyl 4-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside 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: 16.0%

methyl 2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside (109914-57-0) + methyl (2,3,4-tetra-O-acetyl-α-L-idopyranosyl bromide)uroate (108032-44-6) → methyl 4-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside (109914-58-1) + methyl 3-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside + methyl 2-azido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-β-D-galactopyranoside (128716-67-6)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; Yield given. Title compound not separated from byproducts; -20 deg C --> -5 deg C, 1 h;

DOI:10.1016/0008-6215(89)85086-4

Reference yield:

(2R,3R,4R,5R,6R)-5-azido-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4-diol (87376-50-9) → methyl 4-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside (109914-58-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 61 percent / toluene-p-sulfonic acid monohydrate / 5 h / Ambient temperature

2: 97 percent / pyridine

3: 1) sodium hydride 2) 90 percent aq. trifluoroacetic acid / 1) N,N-dimethylformamid, stirred for 1 h 2) room temp., 10 min.

4: toluene-p-sulfonic acid monohydrate 2) 80 percent aq. acetic acid / 1) toluene, room temp., 1 h 2) room temp., 10 min.

With pyridine; sodium hydride; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; toluene-4-sulfonic acid;

DOI:10.1016/S0008-6215(00)90218-0

Reference yield:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl nitrate (68733-05-1) → methyl 4-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside (109914-58-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 60 percent / M sodium methoxyde / 1 h / Ambient temperature

2: 61 percent / toluene-p-sulfonic acid monohydrate / 5 h / Ambient temperature

3: 97 percent / pyridine

4: 1) sodium hydride 2) 90 percent aq. trifluoroacetic acid / 1) N,N-dimethylformamid, stirred for 1 h 2) room temp., 10 min.

5: toluene-p-sulfonic acid monohydrate 2) 80 percent aq. acetic acid / 1) toluene, room temp., 1 h 2) room temp., 10 min.

With pyridine; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; toluene-4-sulfonic acid;

DOI:10.1016/S0008-6215(00)90218-0

upstream raw materials:

Trimethyl orthoacetate

methyl 2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside

methyl (2,3,4-tetra-O-acetyl-α-L-idopyranosyl bromide)uroate

(2R,3R,4R,5R,6R)-5-azido-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4-diol

Downstream raw materials:

methyl 2-acetamido-2-deoxy-3-O-(α-L-idopyranosyluronic acid)-4-O-sulfo-β-D-galactopyranoside, disodium salt

methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-benzyl-α-L-idopyranuronate)-β-D-galactopyranoside

methyl 2-acetamido-4-O-acetyl-6-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside

methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-sulfo-3-O-(2,3,4-tri-O-benzyl-β-L-idopyranosyluronic acid)-β-D-galactopyranoside, disodium salt