(2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

Base Information

• Chemical Name: (2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate
• CAS No.: 1564245-73-3
• Molecular Formula: C₂₁H₃₁BClNO₆
• Molecular Weight: 439.744
• Mol file: 1564245-73-3.mol

Synonyms:(2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

Chemical Property of (2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

There total 2 articles about (2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate 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: 50.0%

(Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)acrylate (1254365-39-3) + bis(pinacol)diborane (73183-34-3) → (2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1564245-73-3) + (2R,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1564245-74-4)

Guidance literature:

bis(pinacol)diborane; With (S,Sp)-ip-FOXAP; copper(l) chloride; sodium t-butanolate; In toluene; at 20 ℃; for 0.5h; Schlenk technique; Molecular sieve; Inert atmosphere;

(Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)acrylate; With methanol; In toluene; at 20 ℃; for 11h; enantioselective reaction; Schlenk technique; Molecular sieve; Inert atmosphere;

DOI:10.1021/ol500219e

Reference yield:

trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate (121056-95-9,89524-98-1) + m-Chlorobenzaldehyde (587-04-2) → (2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1564245-73-3) + (2R,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1564245-74-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 20 °C

2.1: (S,Sp)-ip-FOXAP; copper(l) chloride; sodium t-butanolate / toluene / 0.5 h / 20 °C / Schlenk technique; Molecular sieve; Inert atmosphere

2.2: 11 h / 20 °C / Schlenk technique; Molecular sieve; Inert atmosphere

With (S,Sp)-ip-FOXAP; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(l) chloride; sodium t-butanolate; In dichloromethane; toluene;

DOI:10.1021/ol500219e

upstream raw materials:

trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate

m-Chlorobenzaldehyde

(Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)acrylate

bis(pinacol)diborane