(2R,3S)-4-Bromo-3-hydroxy-2-methyl-pent-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

Base Information

Chemical Name:(2R,3S)-4-Bromo-3-hydroxy-2-methyl-pent-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester
CAS No.:795306-38-6
Molecular Formula:C₃₁H₃₆BrNO₅S
Molecular Weight:614.601
Hs Code.:

Synonyms:(2R,3S)-4-Bromo-3-hydroxy-2-methyl-pent-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

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Chemical Property of (2R,3S)-4-Bromo-3-hydroxy-2-methyl-pent-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

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Technology Process of (2R,3S)-4-Bromo-3-hydroxy-2-methyl-pent-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

There total 2 articles about (2R,3S)-4-Bromo-3-hydroxy-2-methyl-pent-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl 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:

: C₄₀H₅₄BNO₄S

: 14925-39-4
2-bromoacrolein

: 795306-38-6
(2R,3S)-4-Bromo-3-hydroxy-2-methyl-pent-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

Guidance literature:: C₄₀H₅₄BNO₄S; 2-bromoacrolein; In hexane; dichloromethane; at -78 - 20 ℃; for 2h;

With dihydrogen peroxide; In methanol; hexane; dichloromethane; at 20 ℃;
DOI:10.1039/b410092a

Reference yield:

: 187324-66-9
(1R,2S)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate

: 795306-38-6
(2R,3S)-4-Bromo-3-hydroxy-2-methyl-pent-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: Et₃N / CH₂Cl₂; hexane / 2 h / -78 °C

2.1: CH₂Cl₂; hexane / 2 h / -78 - 20 °C

2.2: 5.65 g / aq. H₂O₂ / CH₂Cl₂; hexane; methanol / 20 °C

With triethylamine; In hexane; dichloromethane;
DOI:10.1039/b410092a

Reference yield:

: 795306-38-6
(2R,3S)-4-Bromo-3-hydroxy-2-methyl-pent-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

: 795306-35-3
C₅₂H₇₇BrO₇Si₂

Guidance literature:: Multi-step reaction with 9 steps

1.1: 62 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

2.1: 86 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

3.1: 88 percent / Ph₃P; imidazole; iodine / CH₂Cl₂ / 12 h / 20 °C

4.1: LDA; LiCl / tetrahydrofuran; hexane / 1.33 h / -78 - 20 °C

4.2: 92 percent / tetrahydrofuran; hexane / 18 h / 0 °C

5.1: 84 percent / LDA; borane-ammonia complex / tetrahydrofuran; hexane / 2 h / 20 °C

6.1: 81 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 0.5 h / 20 °C

7.1: n-BuLi / tetrahydrofuran / 0.17 h / -78 °C

7.2: 76 percent / tetrahydrofuran / 0.17 h / -78 °C

8.1: 86 percent / PDC; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

9.1: KHMDS / tetrahydrofuran; toluene / 0.17 h / -78 °C

9.2: 45 percent / tetrahydrofuran; toluene / 15 h / -78 - 20 °C

With 1H-imidazole; ammonia borane; dipyridinium dichromate; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; toluene; 4.2: Myers alkylation;
DOI:10.1039/b410092a