Trichloro-acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-((2S,3R)-3-methyl-oxiranyl)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Trichloro-acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-((2S,3R)-3-methyl-oxiranyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 131750-95-3
• Molecular Formula: C₂₅H₂₇Cl₃O₇
• Molecular Weight: 545.844
• Mol file: 131750-95-3.mol

Synonyms:

Chemical Property of Trichloro-acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-((2S,3R)-3-methyl-oxiranyl)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Trichloro-acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-((2S,3R)-3-methyl-oxiranyl)-tetrahydro-pyran-3-yl ester

There total 5 articles about Trichloro-acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-((2S,3R)-3-methyl-oxiranyl)-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:

methyl (E)-2,3-di-O-benzyl-6,7,8-trideoxy-α-D-galacto-oct-6-enopyranoside (124780-66-1) → Trichloro-acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-((2S,3R)-3-methyl-oxiranyl)-tetrahydro-pyran-3-yl ester (131750-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Na₂CO₃, m-chloroperbenzoic acid / CH₂Cl₂ / 12 h / Heating

2: 1.) t-BuOK / 1.) THF, 5 min, 2.) 2 d

With potassium tert-butylate; sodium carbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1071/CH9901657

Reference yield:

methyl (E)-4-O-benzoyl-2,3-di-O-benzyl-6,7,8-trideoxy-α-D-galacto-oct-6-enoside (124780-54-7) → Trichloro-acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-((2S,3R)-3-methyl-oxiranyl)-tetrahydro-pyran-3-yl ester (131750-95-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / acetic acid, N-bromosuccinimide / CH₂Cl₂; H₂O / 2 h

2: KOH / methanol / 24 h

3: 1.) t-BuOK / 1.) THF, 5 min, 2.) 2 d

With potassium hydroxide; N-Bromosuccinimide; potassium tert-butylate; acetic acid; In methanol; dichloromethane; water;

DOI:10.1071/CH9901657

Reference yield:

methyl 6,7-anhydro-2,3-di-O-benzyl-4-O-carbamoyl-8-deoxy-α-D-threo-D-galacto-octoside (131751-01-4) → Trichloro-acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-((2S,3R)-3-methyl-oxiranyl)-tetrahydro-pyran-3-yl ester (131750-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / t-BuOK / tetrahydrofuran / 2 h / Heating

2: 1.) t-BuOK / 1.) THF, 5 min, 2.) 2 d

With potassium tert-butylate; In tetrahydrofuran;

DOI:10.1071/CH9901657

upstream raw materials:

methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-α-D-threo-D-galacto-octopyranoside

trichloroacetonitrile

methyl (E)-2,3-di-O-benzyl-6,7,8-trideoxy-α-D-galacto-oct-6-enopyranoside

methyl (E)-4-O-benzoyl-2,3-di-O-benzyl-6,7,8-trideoxy-α-D-galacto-oct-6-enoside