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

Base Information

Chemical Name:(2R,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate
CAS No.:1564245-56-2
Molecular Formula:C₂₁H₃₂BNO₆
Molecular Weight:405.299
Hs Code.:

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

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

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

There total 4 articles about (2R,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenyl-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: 54.0%

: 63658-18-4
methyl (Z)-N-Boc-α,β-didehydrophenylalaninate

: 73183-34-3
bis(pinacol)diborane

: 1564245-55-1
(2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

: 1564245-56-2
(2R,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

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;

methyl (Z)-N-Boc-α,β-didehydrophenylalaninate; With methanol; In toluene; at 20 ℃; for 12h; Reagent/catalyst; Concentration; Time; enantioselective reaction; Schlenk technique; Molecular sieve; Inert atmosphere;
DOI:10.1021/ol500219e

Reference yield:

: 63658-18-4
methyl (Z)-N-Boc-α,β-didehydrophenylalaninate

: 73183-34-3
bis(pinacol)diborane

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

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

: 1564245-55-1
(2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

: 1564245-56-2
(2R,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

Guidance literature:: bis(pinacol)diborane; With (R,R)-(?)-2,3-bis(t-butylmethylphosphino)quinoxaline; copper(l) chloride; sodium t-butanolate; In toluene; at 20 ℃; for 0.5h; Schlenk technique; Molecular sieve; Inert atmosphere;

methyl (Z)-N-Boc-α,β-didehydrophenylalaninate; With methanol; In toluene; at 20 ℃; for 12h; Reagent/catalyst; Overall yield = 51 %; enantioselective reaction; Schlenk technique; Molecular sieve; Inert atmosphere;
DOI:10.1021/ol500219e

Reference yield:

: 121056-95-9,89524-98-1
trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate

: 1564245-55-1
(2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

: 1564245-56-2
(2R,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

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: 12 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