(2R,3S,4R)-4-Benzyloxy-2-chloro-3-hydroxy-pentanoic acid (1R,2S)-1-(toluene-4-sulfonylamino)-indan-2-yl ester

Base Information

• Chemical Name: (2R,3S,4R)-4-Benzyloxy-2-chloro-3-hydroxy-pentanoic acid (1R,2S)-1-(toluene-4-sulfonylamino)-indan-2-yl ester
• CAS No.: 745832-02-4
• Molecular Formula: C₂₈H₃₀ClNO₆S
• Molecular Weight: 544.068
• Mol file: 745832-02-4.mol

Synonyms:(2R,3S,4R)-4-Benzyloxy-2-chloro-3-hydroxy-pentanoic acid (1R,2S)-1-(toluene-4-sulfonylamino)-indan-2-yl ester

Chemical Property of (2R,3S,4R)-4-Benzyloxy-2-chloro-3-hydroxy-pentanoic acid (1R,2S)-1-(toluene-4-sulfonylamino)-indan-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-4-Benzyloxy-2-chloro-3-hydroxy-pentanoic acid (1R,2S)-1-(toluene-4-sulfonylamino)-indan-2-yl ester

There total 3 articles about (2R,3S,4R)-4-Benzyloxy-2-chloro-3-hydroxy-pentanoic acid (1R,2S)-1-(toluene-4-sulfonylamino)-indan-2-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: 94.0%

(R)-2-benzyloxypropanal (53346-05-7,41954-96-5,81445-44-5,81445-45-6) + Chloro-acetic acid (1R,2S)-1-(toluene-4-sulfonylamino)-indan-2-yl ester (745831-83-8) → (2R,3S,4R)-4-Benzyloxy-2-chloro-3-hydroxy-pentanoic acid (1R,2S)-1-(toluene-4-sulfonylamino)-indan-2-yl ester (745832-02-4)

Guidance literature:

Chloro-acetic acid (1R,2S)-1-(toluene-4-sulfonylamino)-indan-2-yl ester; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃;

(R)-2-benzyloxypropanal; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.0833333h;

DOI:10.1021/ol0490835

Reference yield: 40.0%

2-(benzyloxy)propanal (53346-05-7) + Chloro-acetic acid (1R,2S)-1-(toluene-4-sulfonylamino)-indan-2-yl ester (745831-83-8) → (S)-2-(benzyloxy)propanal (81445-44-5) + (2R,3R,4S)-4-Benzyloxy-2-chloro-3-hydroxy-pentanoic acid (1R,2S)-1-(toluene-4-sulfonylamino)-indan-2-yl ester (745831-98-5) + (2R,3S,4R)-4-Benzyloxy-2-chloro-3-hydroxy-pentanoic acid (1R,2S)-1-(toluene-4-sulfonylamino)-indan-2-yl ester (745832-02-4)

Guidance literature:

Chloro-acetic acid (1R,2S)-1-(toluene-4-sulfonylamino)-indan-2-yl ester; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃;

2-(benzyloxy)propanal; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1021/ol0490835

Reference yield:

(+)-(1R,2S)-1-(N-tosylamino)-2-indanol (175523-35-0) → (2R,3S,4R)-4-Benzyloxy-2-chloro-3-hydroxy-pentanoic acid (1R,2S)-1-(toluene-4-sulfonylamino)-indan-2-yl ester (745832-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 94 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

2.1: TiCl₄; iPr₂NEt / CH₂Cl₂ / 0 °C

2.2: 94 percent / TiCl₄ / CH₂Cl₂ / 0.08 h / -78 °C

With pyridine; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/ol0490835

upstream raw materials:

2-(benzyloxy)propanal

Chloro-acetic acid (1R,2S)-1-(toluene-4-sulfonylamino)-indan-2-yl ester

(R)-2-benzyloxypropanal

(+)-(1R,2S)-1-(N-tosylamino)-2-indanol