(2S,3S)-2-[(E)-(1S,2R)-4-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-2-methyl-1-phenyl-but-3-enyl]-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester

Base Information

• Chemical Name: (2S,3S)-2-[(E)-(1S,2R)-4-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-2-methyl-1-phenyl-but-3-enyl]-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester
• CAS No.: 164334-44-5
• Molecular Formula: C₃₇H₅₃N₂O₅P
• Molecular Weight: 636.812
• Mol file: 164334-44-5.mol

Synonyms:

Chemical Property of (2S,3S)-2-[(E)-(1S,2R)-4-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-2-methyl-1-phenyl-but-3-enyl]-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-[(E)-(1S,2R)-4-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-2-methyl-1-phenyl-but-3-enyl]-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester

There total 1 articles about (2S,3S)-2-[(E)-(1S,2R)-4-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-2-methyl-1-phenyl-but-3-enyl]-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl 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: 52.0%

(E)-isopropyl cinnamate (60512-85-8) + Lithium; (1Z,5E)-(3S,4R)-1-tert-butoxy-6-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-4-methyl-3-phenyl-hexa-1,5-dien-1-olate → (2S,3S)-2-[(E)-(1S,2R)-4-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-2-methyl-1-phenyl-but-3-enyl]-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester (164334-44-5) + (2S,3R)-2-[(E)-(1S,2R)-4-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-2-methyl-1-phenyl-but-3-enyl]-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester

Guidance literature:

In tetrahydrofuran; hexane; at -78 - -65 ℃; for 1h; Product distribution; Mechanism; further enolates generated from other bicyclic chiral phosphoramide with other cinnamate ester; diastereoselectivity; further quenching agents;

DOI:10.1016/S0040-4039(00)78330-4

Reference yield:

(2S,3S)-2-[(E)-(1S,2R)-4-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-2-methyl-1-phenyl-but-3-enyl]-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester (164334-44-5) → (2S,3S)-2-((1S,2R)-2-Methyl-3-oxo-1-phenyl-propyl)-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester

Guidance literature:

With ozone; In methanol; dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(00)78330-4

Reference yield:

(2S,3S)-2-[(E)-(1S,2R)-4-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-2-methyl-1-phenyl-but-3-enyl]-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester (164334-44-5) → (2S,3S)-2-((1R,2R)-3-Bromo-2-methyl-1-phenyl-propyl)-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: O₃ / CH₂Cl₂; methanol / -78 °C

2: NaBH₄

3: 71 percent / triphenylphosphine, CBr₄

With sodium tetrahydroborate; carbon tetrabromide; ozone; triphenylphosphine; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)78330-4

upstream raw materials:

(E)-isopropyl cinnamate

Downstream raw materials:

(2S,3S)-2-((1S,2R)-3-Hydroxy-2-methyl-1-phenyl-propyl)-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester