(2'S,3'S)-1D-1-O-[(S)-(+)-O-acetylmandelyl]-3,6-di-O-benzyl-4,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-myo-inositol

Base Information

• Chemical Name: (2'S,3'S)-1D-1-O-[(S)-(+)-O-acetylmandelyl]-3,6-di-O-benzyl-4,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-myo-inositol
• CAS No.: 221462-08-4
• Molecular Formula: C₃₆H₄₂O₁₁
• Molecular Weight: 650.723
• Mol file: 221462-08-4.mol

Synonyms:(2'S,3'S)-1D-1-O-[(S)-(+)-O-acetylmandelyl]-3,6-di-O-benzyl-4,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-myo-inositol

Chemical Property of (2'S,3'S)-1D-1-O-[(S)-(+)-O-acetylmandelyl]-3,6-di-O-benzyl-4,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-myo-inositol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'S,3'S)-1D-1-O-[(S)-(+)-O-acetylmandelyl]-3,6-di-O-benzyl-4,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-myo-inositol

There total 1 articles about (2'S,3'S)-1D-1-O-[(S)-(+)-O-acetylmandelyl]-3,6-di-O-benzyl-4,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-myo-inositol 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: 36.0%

(S)-acetylmandelic acid (7322-88-5) + (2'RS,3'RS)-DL-1,4-di-O-benzyl-5,6-O-(2',3'-dimethoxybutane-2',3'-diyl)-myo-inositol → (2'S,3'S)-1D-1-O-[(S)-(+)-O-acetylmandelyl]-3,6-di-O-benzyl-4,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-myo-inositol (221462-08-4) + (2'R,3'R)-1D-3-O-[(S)-(+)-O-acetylmandelyl]-1,4-di-O-benzyl-5,6-O-(2',3'-dimethoxybutane-2',3'-diyl)-myo-inositol (221462-07-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at -20 ℃; to rt;

DOI:10.1016/S0040-4039(99)00174-4

Reference yield: 95.0%

(2'S,3'S)-1D-1-O-[(S)-(+)-O-acetylmandelyl]-3,6-di-O-benzyl-4,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-myo-inositol (221462-08-4) → (2'S,3'S)-1D-3,6-di-O-benzyl-4,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-myo-inositol (221462-15-3)

Guidance literature:

With sodium hydroxide; In methanol; Heating;

DOI:10.1016/S0040-4039(99)00174-4

Reference yield:

(2'S,3'S)-1D-1-O-[(S)-(+)-O-acetylmandelyl]-3,6-di-O-benzyl-4,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-myo-inositol (221462-08-4) → (2'R)-1D-3,6-di-O-benzyl-1,2-O-[(2'-hydroxy)propane-1',3'-diyl]-myo-inositol (221553-96-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 95 percent / NaOH / methanol / 1 h / Heating

2.1: NaH / dimethylformamide / 0.5 h / 20 °C

2.2: 84 percent / dimethylformamide / 1 h

3.1: 82 percent / NaIO₄; aq. RuCl₃ / ethyl acetate; acetonitrile / 1.5 h / 20 °C

4.1: 67 percent / NaBH₄ / methanol / 0 - 20 °C

5.1: 84 percent / 95percent aq. TFA / CH₂Cl₂ / 0.25 h / 20 °C

With ruthenium trichloride; sodium hydroxide; sodium tetrahydroborate; sodium periodate; sodium hydride; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm0005499

upstream raw materials:

(S)-acetylmandelic acid

Downstream raw materials:

(2'S,3'S)-1D-3,6-di-O-benzyl-4,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-myo-inositol

(2'R)-1D-3,6-di-O-benzyl-1,2-O-[(2'-hydroxy)propane-1',3'-diyl]-myo-inositol

(2'S)-1D-3,6-di-O-benzyl-1,2-O-[(2'-hydroxy)propane-1',3'-diyl]-myo-inositol

(2'S,3'S)-1D-3,6-di-O-benzyl-4,5-(2',3'-dimethoxybutane-2',3'-diyl)-1,2-O-[(2''-oxo)propane-1'',3''-diyl]-myo-inositol