ethyl (2R,3S)-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]oxy}propanoate

Base Information

Chemical Name:ethyl (2R,3S)-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]oxy}propanoate
CAS No.:864181-28-2
Molecular Formula:C₂₅H₂₄BrClO₇S
Molecular Weight:583.884
Hs Code.:

Synonyms:ethyl (2R,3S)-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]oxy}propanoate

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Chemical Property of ethyl (2R,3S)-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]oxy}propanoate

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Technology Process of ethyl (2R,3S)-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]oxy}propanoate

There total 5 articles about ethyl (2R,3S)-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]oxy}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: 81.0%

: 864181-27-1
ethyl (2R,3S)-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-2,3-dihydroxypropanoate

: 98-59-9
p-toluenesulfonyl chloride

: 864181-28-2
ethyl (2R,3S)-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]oxy}propanoate

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1016/j.tetasy.2005.05.023

Reference yield:

: 864181-25-9
2-(benzyloxy)-1,5-dibromo-3-chlorobenzene

: 864181-28-2
ethyl (2R,3S)-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]oxy}propanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / Pd(OAc)2; TPP; Et₃N / dimethylformamide / 12 h / 100 °C

2: 95 percent / OsO₄; NMO; (DHQ)2PHAL / various solvent(s) / 3 h / 20 °C

3: 81 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

With palladium diacetate; osmium(VIII) oxide; N-methyl-2-indolinone; Hydroquinone 1,4-phthalazinediyl diether; thiamine diphosphate; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1: Heck coupling / 2: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetasy.2005.05.023

Reference yield:

: 864181-26-0
ethyl (2E)-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]acrylate

: 864181-28-2
ethyl (2R,3S)-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]oxy}propanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / OsO₄; NMO; (DHQ)2PHAL / various solvent(s) / 3 h / 20 °C

2: 81 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; Hydroquinone 1,4-phthalazinediyl diether; triethylamine; In dichloromethane; 1: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetasy.2005.05.023