methyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranuronate

Base Information

• Chemical Name: methyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranuronate
• CAS No.: 117780-21-9
• Molecular Formula: C₂₃H₂₅ClO₈
• Molecular Weight: 464.9
• Mol file: 117780-21-9.mol

Synonyms:methyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranuronate

Chemical Property of methyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranuronate

There total 46 articles about methyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranuronate 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:

methyl (allyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosid)uronate (117780-19-5) → (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-(2-chloro-acetoxy)-6-(2-oxo-propoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (117780-22-0) + methyl 2,3-di-O-benzyl-4-O-chloroacetyl-D-galactopyranuronate (93338-32-0,117780-21-9)

Guidance literature:

With sodium acetate; palladium dichloride; In acetic acid; at 30 - 35 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts; ultrasonication;

DOI:10.1016/S0008-6215(00)90828-0

Reference yield:

methyl (allyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosid)uronate (117780-19-5) → (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-(2-chloro-acetoxy)-6-(2-oxo-propoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (117780-22-0) + methyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranuronate (117780-21-9)

Guidance literature:

With sodium acetate; palladium dichloride; In acetic acid; at 30 - 35 ℃; Yields of byproduct given. Title compound not separated from byproducts; ultrasonication;

DOI:10.1016/S0008-6215(00)90828-0

Reference yield:

allyl β-D-galactopyranoside (2595-07-5,821794-45-0) → methyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranuronate (117780-21-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 55.9 percent / p-toluenesulfonic acid / dimethylformamide / 5 h / Ambient temperature

2: 55.7 percent / 60 percent NaH / dimethylformamide / 1.) 1 h; 2.) 0.5 h, 0 deg C; 3.) 2.5 h, RT

3: 1.) t-BuOK; 2.) I₂, pyridine / 1.) DMSO, 60 deg C, 3 h; 2.) aq. THF, 30 min, RT

4: imidazole / dimethylformamide / 7 h / 60 °C

5: 79.3 percent / 80 percent AcOH / tetrahydrofuran / Ambient temperature

7: pyridine

8: benzenesulfonic acid / CHCl₃; methanol

9: oxalyl chloride, Et₃N / CH₂Cl₂; dimethylsulfoxide

10: Jones reagent / acetone

11: diethyl ether

12: 50 percent HF, pyridine / 24 h / Ambient temperature

With pyridine; 1H-imidazole; jones reagent; oxalyl dichloride; hydrogen fluoride; potassium tert-butylate; iodine; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; benzenesulfonic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0008-6215(00)90828-0

upstream raw materials:

methyl (allyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosid)uronate

benzyl bromide

allyl 2,3-di-Ο-benzyl-β-D-galactopyranoside

allyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranoside

Downstream raw materials:

methyl (2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosyl fluoride)uronate

methyl (2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl fluoride)uronate