Chloro-acetic acid (2S,3S,4S,5R,6R)-2-[(2R,3R,4S,5S,6S)-4-acetoxy-3,5-bis-benzyloxy-6-(4,5-dibromo-pentyloxy)-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Chloro-acetic acid (2S,3S,4S,5R,6R)-2-[(2R,3R,4S,5S,6S)-4-acetoxy-3,5-bis-benzyloxy-6-(4,5-dibromo-pentyloxy)-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 130350-39-9
• Molecular Formula: C₅₆H₆₃Br₂ClO₁₃
• Molecular Weight: 1139.37
• Mol file: 130350-39-9.mol

Synonyms:

Chemical Property of Chloro-acetic acid (2S,3S,4S,5R,6R)-2-[(2R,3R,4S,5S,6S)-4-acetoxy-3,5-bis-benzyloxy-6-(4,5-dibromo-pentyloxy)-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Chloro-acetic acid (2S,3S,4S,5R,6R)-2-[(2R,3R,4S,5S,6S)-4-acetoxy-3,5-bis-benzyloxy-6-(4,5-dibromo-pentyloxy)-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

There total 2 articles about Chloro-acetic acid (2S,3S,4S,5R,6R)-2-[(2R,3R,4S,5S,6S)-4-acetoxy-3,5-bis-benzyloxy-6-(4,5-dibromo-pentyloxy)-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-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:

Acetic acid (2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-hydroxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-4-yl ester (130327-14-9) → Chloro-acetic acid (2S,3S,4S,5R,6R)-2-[(2R,3R,4S,5S,6S)-4-acetoxy-3,5-bis-benzyloxy-6-(4,5-dibromo-pentyloxy)-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (130350-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Br₂, Bu₄NBr

2: NIS/ Et₃SiOTf

With N-iodo-succinimide; tetrabutylammomium bromide; bromine; triethylsilyl trifluoromethyl sulfonate;

DOI:10.1021/jo00312a004

Reference yield:

Acetic acid (2S,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-(4,5-dibromo-pentyloxy)-6-hydroxymethyl-tetrahydro-pyran-4-yl ester (130350-38-8) + Chloro-acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yl ester (123487-57-0) → Chloro-acetic acid (2S,3S,4S,5R,6R)-2-[(2R,3R,4S,5S,6S)-4-acetoxy-3,5-bis-benzyloxy-6-(4,5-dibromo-pentyloxy)-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (130350-39-9)

Guidance literature:

With N-iodo-succinimide; triethylsilyl trifluoromethyl sulfonate;

DOI:10.1021/jo00312a004

Reference yield:

Acetic acid (2S,3S,4S,5R,6R)-3-acetoxy-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-tetrahydro-pyran-4-yl ester (130327-17-2) + Chloro-acetic acid (2S,3S,4S,5R,6R)-2-[(2R,3R,4S,5S,6S)-4-acetoxy-3,5-bis-benzyloxy-6-(4,5-dibromo-pentyloxy)-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (130350-39-9) → C87H100Br2O19Si (130327-15-0)

Guidance literature:

With N-iodo-succinimide; triethylsilyl trifluoromethyl sulfonate; thiourea; Multistep reaction;

DOI:10.1021/jo00312a004

upstream raw materials:

Acetic acid (2S,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-(4,5-dibromo-pentyloxy)-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

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

Acetic acid (2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-hydroxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-4-yl ester

Downstream raw materials:

C₈₇H₁₀₀Br₂O₁₉Si