ethyl (2S,3S)-2-azido-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-3-hydroxypropanoate

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Chemical Name:ethyl (2S,3S)-2-azido-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-3-hydroxypropanoate
CAS No.:864181-29-3
Molecular Formula:C₁₈H₁₇BrClN₃O₄
Molecular Weight:454.708
Hs Code.:

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

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

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

There total 6 articles about ethyl (2S,3S)-2-azido-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-3-hydroxypropanoate 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: 72.0%

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

: 864181-29-3
ethyl (2S,3S)-2-azido-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-3-hydroxypropanoate

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 65 ℃; for 10h;
DOI:10.1016/j.tetasy.2005.05.023

Reference yield:

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

: 864181-29-3
ethyl (2S,3S)-2-azido-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-3-hydroxypropanoate

Guidance literature:: Multi-step reaction with 4 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

4: 72 percent / NaN₃ / dimethylformamide / 10 h / 65 °C

With palladium diacetate; osmium(VIII) oxide; sodium azide; 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

: 864181-29-3
ethyl (2S,3S)-2-azido-3-[4-(benzyloxy)-3-bromo-5-chlorophenyl]-3-hydroxypropanoate

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 72 percent / NaN₃ / dimethylformamide / 10 h / 65 °C

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