1-(p-tolylsulfonyl)-4(S)-<(benzyloxy)methyl>cyclopent-5-eno<4,5-d>-(3aR,6aS)-oxazolidin-2-one

Base Information

• Chemical Name: 1-(p-tolylsulfonyl)-4(S)-<(benzyloxy)methyl>cyclopent-5-eno<4,5-d>-(3aR,6aS)-oxazolidin-2-one
• CAS No.: 143729-91-3
• Molecular Formula: C₂₁H₂₁NO₅S
• Molecular Weight: 399.467
• Mol file: 143729-91-3.mol

Synonyms:1-(p-tolylsulfonyl)-4(S)-<(benzyloxy)methyl>cyclopent-5-eno<4,5-d>-(3aR,6aS)-oxazolidin-2-one

Chemical Property of 1-(p-tolylsulfonyl)-4(S)-<(benzyloxy)methyl>cyclopent-5-eno<4,5-d>-(3aR,6aS)-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(p-tolylsulfonyl)-4(S)-<(benzyloxy)methyl>cyclopent-5-eno<4,5-d>-(3aR,6aS)-oxazolidin-2-one

There total 3 articles about 1-(p-tolylsulfonyl)-4(S)-<(benzyloxy)methyl>cyclopent-5-eno<4,5-d>-(3aR,6aS)-oxazolidin-2-one 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:

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol (100021-11-2) + Tosyl isocyanate (4083-64-1) → 1-(p-tolylsulfonyl)-4(R)-<(benzyloxy)methyl>cyclopent-5-eno<4,5-d>-(3aS,6aR)-oxazolidin-2-one + 1-(p-tolylsulfonyl)-4(S)-<(benzyloxy)methyl>cyclopent-5-eno<4,5-d>-(3aR,6aS)-oxazolidin-2-one (143729-91-3)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (S,S)-ANDEN-Phenyl Trost Ligand; In tetrahydrofuran; at 50 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/ja00050a013

Reference yield:

5-(benzyloxymethyl)cyclopentadiene (39939-07-6) → (+/-)-4S-<(benzyloxy)methyl>-1-<(4'-methylphenyl)sulfonyl>cyclopent-5-eno<4,5-d>-3aR,6aS-1,3-oxazolidinone (124583-65-9,143729-91-3,143729-95-7)

Guidance literature:

Multi-step reaction with 2 steps

1: thiourea, O₂, methylene blue / methanol / 0 °C / Irradiation

2: 2.) (dba)3Pd₂*CHCl₃, (i-PrO)3P / 1.) THF, 2.) room temp.

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triisopropyl phosphite; oxygen; methylene blue; thiourea; In methanol;

Reference yield:

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol (100021-11-2) + Tosyl isocyanate (4083-64-1) → (+/-)-4S-<(benzyloxy)methyl>-1-<(4'-methylphenyl)sulfonyl>cyclopent-5-eno<4,5-d>-3aR,6aS-1,3-oxazolidinone (124583-65-9,143729-91-3,143729-95-7)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triisopropyl phosphite; Yield given. Multistep reaction; 1.) THF, 2.) room temp.;

upstream raw materials:

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

Tosyl isocyanate

5-(benzyloxymethyl)cyclopentadiene

Downstream raw materials:

(+/-)-4S-<(benzyloxy)methyl>cyclopent-5-eno<4,5-d>-3aR,6aS-oxazolidin-2-one

(+/-)-4S-<(benzyloxy)methyl>-2-(N,N-dimethylamino)cyclopent-5-eno<4,5-d>-3aS,6aR-oxzoline

((1bR,4aR,5R)-5-Benzyloxymethyl-1b,4a,5,5a-tetrahydro-1aH-1,4-dioxa-2-aza-cyclopropa[a]pentalen-3-yl)-dimethyl-amine

(+/-)-allosamizoline