(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-(2-chloro-acetoxy)-6-(2-oxo-propoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-(2-chloro-acetoxy)-6-(2-oxo-propoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 117780-22-0
• Molecular Formula: C₂₆H₂₉ClO₉
• Molecular Weight: 520.964
• Mol file: 117780-22-0.mol

Synonyms:(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-(2-chloro-acetoxy)-6-(2-oxo-propoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-(2-chloro-acetoxy)-6-(2-oxo-propoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-(2-chloro-acetoxy)-6-(2-oxo-propoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 12 articles about (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-(2-chloro-acetoxy)-6-(2-oxo-propoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 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) → (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)

Guidance literature:

Multi-step reaction with 9 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: 92.1 percent / 80 percent aq. AcOH / 1 h / 60 °C

4: pyridine / 3 h / Ambient temperature

5: pyridine / 3.5 h

6: 2 percent benzenesulfonic acid / CHCl₃; methanol / 0.5 h

7: 46 percent / 8 N Jones reagent / acetone / 2 h

8: diethyl ether

9: NaOAc / PdCl₂ / aq. acetic acid / 30 - 35 °C / ultrasonication

With jones reagent; sodium acetate; sodium hydride; toluene-4-sulfonic acid; acetic acid; benzenesulfonic acid; palladium dichloride; In pyridine; methanol; diethyl ether; chloroform; acetic acid; 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

allyl β-D-galactopyranoside

benzyl bromide

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