Chloro-acetic acid (2R,3S,4S,5R,6R)-2-acetoxymethyl-6-((2R,3S,4S,5R,6R)-2-acetoxymethyl-6-allyloxy-4,5-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Chloro-acetic acid (2R,3S,4S,5R,6R)-2-acetoxymethyl-6-((2R,3S,4S,5R,6R)-2-acetoxymethyl-6-allyloxy-4,5-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-3-yl ester
• CAS No.: 113765-27-8
• Molecular Formula: C₄₉H₅₅ClO₁₄
• Molecular Weight: 903.42
• Mol file: 113765-27-8.mol

Synonyms:

Chemical Property of Chloro-acetic acid (2R,3S,4S,5R,6R)-2-acetoxymethyl-6-((2R,3S,4S,5R,6R)-2-acetoxymethyl-6-allyloxy-4,5-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Chloro-acetic acid (2R,3S,4S,5R,6R)-2-acetoxymethyl-6-((2R,3S,4S,5R,6R)-2-acetoxymethyl-6-allyloxy-4,5-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-3-yl ester

There total 2 articles about Chloro-acetic acid (2R,3S,4S,5R,6R)-2-acetoxymethyl-6-((2R,3S,4S,5R,6R)-2-acetoxymethyl-6-allyloxy-4,5-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-3-yl 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: 83.0%

allyl 6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside (113765-20-1) + Chloro-acetic acid (2R,3S,4S,5R)-2-acetoxymethyl-4,5-bis-benzyloxy-6-fluoro-tetrahydro-pyran-3-yl ester (113765-16-5,113765-35-8) → Chloro-acetic acid (2R,3S,4S,5R,6R)-2-acetoxymethyl-6-((2R,3S,4S,5R,6R)-2-acetoxymethyl-6-allyloxy-4,5-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-3-yl ester (113765-27-8)

Guidance literature:

In diethyl ether; for 20h; -15 deg C to room temperature;

DOI:10.1016/S0040-4039(00)96193-8

Reference yield:

allyl 2,3-di-Ο-benzyl-β-D-galactopyranoside (97817-99-7) → Chloro-acetic acid (2R,3S,4S,5R,6R)-2-acetoxymethyl-6-((2R,3S,4S,5R,6R)-2-acetoxymethyl-6-allyloxy-4,5-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-3-yl ester (113765-27-8)

Guidance literature:

Multi-step reaction with 2 steps

1: acetylation

2: 83 percent / diethyl ether / 20 h / -15 deg C to room temperature

In diethyl ether;

DOI:10.1016/S0040-4039(00)96193-8

Reference yield:

Chloro-acetic acid (2R,3S,4S,5R,6R)-2-acetoxymethyl-6-((2R,3S,4S,5R,6R)-2-acetoxymethyl-6-allyloxy-4,5-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-3-yl ester (113765-27-8) → C70H80O18 (128745-62-0)

Guidance literature:

Multi-step reaction with 2 steps

1: dechloroacetylation

2: 2.) pyridine / 1.) Et₂O-toluene, -15 deg C, 6 h

With pyridine;

DOI:10.1016/S0040-4039(00)96193-8

upstream raw materials:

allyl 6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside

Chloro-acetic acid (2R,3S,4S,5R)-2-acetoxymethyl-4,5-bis-benzyloxy-6-fluoro-tetrahydro-pyran-3-yl ester

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

Downstream raw materials:

allyl O-(6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl)-(1->4)-6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside

allyl O-(2,3-di-O-benzyl-α-D-galactopyranosyl)-(1->4)-O-(6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl)-(1->4)-6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside

C₇₀H₈₀O₁₈