(3R,5S)-5-(HYDROXYMETHYL)-1-TOSYLPYRROLIDIN-3-YL 4-METHYLBENZENESULFONATE

Base Information

• Chemical Name: (3R,5S)-5-(HYDROXYMETHYL)-1-TOSYLPYRROLIDIN-3-YL 4-METHYLBENZENESULFONATE
• CAS No.: 118329-82-1
• Molecular Formula: C19H23NO6S2
• Molecular Weight: 425.527
• Mol file: 118329-82-1.mol

Synonyms:(3R,5S)-5-(HYDROXYMETHYL)-1-TOSYLPYRROLIDIN-3-YL 4-METHYLBENZENESULFONATE

Chemical Property of (3R,5S)-5-(HYDROXYMETHYL)-1-TOSYLPYRROLIDIN-3-YL 4-METHYLBENZENESULFONATE

Chemical Property:

• PSA: 117.74000
• LogP: 3.93230

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3R,5S)-5-(HYDROXYMETHYL)-1-TOSYLPYRROLIDIN-3-YL 4-METHYLBENZENESULFONATE

There total 8 articles about (3R,5S)-5-(HYDROXYMETHYL)-1-TOSYLPYRROLIDIN-3-YL 4-METHYLBENZENESULFONATE 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: 91.0%

(2S,4R)-2-ethoxycarbonyl-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine (118329-81-0) → (2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine (118329-82-1)

Guidance literature:

With sodium tetrahydroborate; lithium chloride; In tetrahydrofuran; ethanol; at 0 ℃; for 3.5h;

DOI:10.1016/j.tetlet.2005.06.025 DOI:10.1039/b711994a

Reference yield: 85.0%

N,O-ditosylhydroxy-L-proline (5260-29-7) → (2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine (118329-82-1)

Guidance literature:

With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2010.04.074

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine (118329-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Et₃N, DMAP / CH₂Cl₂ / 48 h / Ambient temperature

2: LiBH₄ / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 1 h

With dmap; lithium borohydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(98)00821-7

upstream raw materials:

N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester

(2S,4R)-2-ethoxycarbonyl-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

4R-4-hydroxyproline

(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid ethyl ester

Downstream raw materials:

(2S,4R)-N-Tosyl-4-tosyloxy-O-benzoylprolinol

Toluene-4-sulfonic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl ester

(2S,4R)-2-(carbamoyloxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

(S)-2-carbamoyloxymethyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole