3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane

Base Information

• Chemical Name: 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane
• CAS No.: 218439-10-2
• Molecular Formula: C₃₀H₂₆NO₃P
• Molecular Weight: 479.515
• Mol file: 218439-10-2.mol

Synonyms:3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane

Chemical Property of 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane

There total 6 articles about 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane 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: 75.0%

4S-3-(2-bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone (129549-13-9) + triphenylphosphine (603-35-0) → 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane (218439-10-2)

Guidance literature:

4S-3-(2-bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone; triphenylphosphine; In toluene; at 20 ℃; for 120h;

With sodium hydroxide;

Reference yield: 50.0%

(4S)-(+)-3-(chloroacetyl)-4-(phenylmethyl)-2-oxazolidinone (104324-16-5) + triphenylphosphine (603-35-0) → 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane (218439-10-2)

Guidance literature:

(4S)-(+)-3-(chloroacetyl)-4-(phenylmethyl)-2-oxazolidinone; triphenylphosphine; In dichloromethane; at 20 ℃; for 48h; Inert atmosphere;

With sodium hydroxide; In water; at 50 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1002/ejoc.202100397

Reference yield:

(4S)-4-benzyl-3-<2-(triphenylphosphonio)acetyl>-2-oxazolidinone bromide (139278-12-9) → 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane (218439-10-2)

Guidance literature:

With sodium hydroxide; In diethyl ether; at 25 ℃; for 2h;

DOI:10.1021/jo00108a022

upstream raw materials:

(4S)-4-benzyl-3-<2-(triphenylphosphonio)acetyl>-2-oxazolidinone bromide

4S-3-(2-bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone

triphenylphosphine

(4S)-(+)-3-(chloroacetyl)-4-(phenylmethyl)-2-oxazolidinone

Downstream raw materials:

(4S)-3-[cis-(4-t-butoxycarbonylaminocyclohexyl)propenoyl]-4-phenylmethyl-2-oxazolidinone

(4S)-3-[trans-(4-t-butoxycarbonylaminocyclohexyl)propenoyl]-4-phenylmethyl-2-oxazolidinone

(2R,1'R,2'R,4S)-ethyl N-diphenylmethylidene-2-<2'-<(4-benzyl-2-oxazolidinon-3-yl)carbonyl>-3',3'-difluoro>cyclopropylglycinate

(S)-4-Benzyl-3-[(2S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butyryl]-oxazolidin-2-one

Refernces

• 1、 Noguchi, Hirohide,Aoyama, Toyohiko,Shioiri, Takayuki. "Total synthesis and absolute configuration of radiosumin, a strong trypsin inhibitor from the blue-green alga Plectonema radiosum". . p. 471 - 504. Retrieved 2007/10/03.
• 2、 Nemoto,Satoh,Fukumoto,Kabuto. "A rapid access to both enantiomers of 1,2,3,4-tetranor B-trienic 18,18,18-trifluorosteroids. The first enantiocontrolled total synthesis of 18,18,18-trifluorosteroids". . p. 594 - 600. Retrieved 2007/10/02.