(2S,3S)-Dimethyl N-(9'-phenylfluoren-9'-yl)-3-hydroxyaspartate

Base Information

• Chemical Name: (2S,3S)-Dimethyl N-(9'-phenylfluoren-9'-yl)-3-hydroxyaspartate
• CAS No.: 144331-15-7
• Molecular Formula: C₂₅H₂₃NO₅
• Molecular Weight: 417.461
• Mol file: 144331-15-7.mol

Synonyms:(2S,3S)-Dimethyl N-(9'-phenylfluoren-9'-yl)-3-hydroxyaspartate

Chemical Property of (2S,3S)-Dimethyl N-(9'-phenylfluoren-9'-yl)-3-hydroxyaspartate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-Dimethyl N-(9'-phenylfluoren-9'-yl)-3-hydroxyaspartate

There total 1 articles about (2S,3S)-Dimethyl N-(9'-phenylfluoren-9'-yl)-3-hydroxyaspartate 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:

dimethyl (S)-N-(9-phenyl-9H-fluoren-9-yl)aspartate (120230-62-8) → (2S,3S)-Dimethyl N-(9'-phenylfluoren-9'-yl)-3-hydroxyaspartate (144331-15-7) + (2S,3R)-Dimethyl N-(9'-phenylfluoren-9'-yl)-3-hydroxyaspartate (144331-16-8)

Guidance literature:

With MoO₅*pyridine*HMPA; lithium hexamethyldisilazane; Product distribution; Mechanism; multistep reaction; chirospecific and stereodivergent synthesis of N-(9-phenylfluorenyl)-3-hydroxyaspartates; other bases, other solvents;

DOI:10.1016/S0040-4039(00)61333-3

Reference yield: 100.0%

phosgene (75-44-5) + (2S,3S)-Dimethyl N-(9'-phenylfluoren-9'-yl)-3-hydroxyaspartate (144331-15-7) → (4S,5S)-2-Oxo-3-(9-phenyl-9H-fluoren-9-yl)-oxazolidine-4,5-dicarboxylic acid dimethyl ester (144331-17-9)

Guidance literature:

With pyridine; dmap; In toluene; at 75 ℃; for 0.416667h;

DOI:10.1021/jo00104a019

Reference yield: 100.0%

N-benzenesulfonyl-L-proline (88425-46-1) + (2S,3S)-Dimethyl N-(9'-phenylfluoren-9'-yl)-3-hydroxyaspartate (144331-15-7) → (2S,3S)-2-((S)-1-Benzenesulfonyl-pyrrolidine-2-carbonyloxy)-3-(9-phenyl-9H-fluoren-9-ylamino)-succinic acid dimethyl ester (144408-12-8)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 2.5h;

DOI:10.1021/jo00104a019

upstream raw materials:

dimethyl (S)-N-(9-phenyl-9H-fluoren-9-yl)aspartate

Downstream raw materials:

(2S,3S)-2-((S)-1-Benzenesulfonyl-pyrrolidine-2-carbonyloxy)-3-(9-phenyl-9H-fluoren-9-ylamino)-succinic acid dimethyl ester

(2S,3S)-2-(1-Benzenesulfonyl-pyrrolidine-2-carbonyloxy)-3-(9-phenyl-9H-fluoren-9-ylamino)-succinic acid dimethyl ester

(4S,5S)-2-Oxo-3-(9-phenyl-9H-fluoren-9-yl)-oxazolidine-4,5-dicarboxylic acid dimethyl ester

methyl (2S,3S)-3,4-dihydroxy-2-(9'-phenylfluoren-9'-ylamino)butyrate

Refernces

• 1、 Sardina, F. Javier,Paz, Manuel M.,Fernandez-Megia, Eduardo,De Boer, Richard F.,Alvarez, M. Pilar. "A stereodivergent chirospecific synthesis of (3R) and (3S) 3-hydroxyaspartates by hydroxylation of aspartate diester enolates". . p. 4637 - 4640. Retrieved 2007/10/02.