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

Base Information

Chemical Name:ethyl (2R,3S)-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-2,3-dihydroxypropanoate
CAS No.:864181-27-1
Molecular Formula:C₁₈H₁₈BrClO₅
Molecular Weight:429.695
Hs Code.:

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

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Chemical Property of ethyl (2R,3S)-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-2,3-dihydroxypropanoate

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Technology Process of ethyl (2R,3S)-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-2,3-dihydroxypropanoate

There total 4 articles about ethyl (2R,3S)-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-2,3-dihydroxypropanoate 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: 95.0%

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

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

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; Hydroquinone 1,4-phthalazinediyl diether; In various solvent(s); at 20 ℃; for 3h;
DOI:10.1016/j.tetasy.2005.05.023

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 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

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

Reference yield:

: 95-57-8
2-monochlorophenol

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

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / N-bromosuccinimide / tetrahydrofuran / 0.5 h / 0 °C

2: 92.2 percent / K₂CO₃ / acetone / 3 h / Heating

3: 90 percent / Pd(OAc)2; TPP; Et₃N / dimethylformamide / 12 h / 100 °C

4: 95 percent / OsO₄; NMO; (DHQ)2PHAL / various solvent(s) / 3 h / 20 °C

With palladium diacetate; N-Bromosuccinimide; osmium(VIII) oxide; N-methyl-2-indolinone; Hydroquinone 1,4-phthalazinediyl diether; thiamine diphosphate; potassium carbonate; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; acetone; 3: Heck coupling / 4: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetasy.2005.05.023