ERYTHRO-N-BOC-O-BENZYL-L-TYROSINE EPOXIDE

Base Information

• Chemical Name: ERYTHRO-N-BOC-O-BENZYL-L-TYROSINE EPOXIDE
• CAS No.: 162536-84-7
• Molecular Formula: C22H27NO4
• Molecular Weight: 369.461
• Mol file: 162536-84-7.mol

Synonyms:(S)-[1-(S)-N-BOC AMINO-2-[4-(BENZYLOXY)PHENYL]ETHYL]OXIRANE;ERYTHRO-N-T-BUTOXYCARBONYL-O-BENZYL-L-TYROSINE EPOXIDE;ERYTHRO-N-BOC-O-BENZYL-L-TYROSINE EPOXIDE;[2-(4-BENZYLOXY-PHENYL)-1(S)-(S)OXIRANYL-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER;(1S)-[1-(S)-N-T-BUTOXYCARBONYL-AMINO-2-[4-(BENZYLOXY)PHENYL]ETHYL]OXIRANE;(1S)-(1-(S)-N-BOC-AMINO-2-[4-(BENZYLOXY)PHENYL]ETHYL)OXIRANE;(S)-(2S,3R)-3,4-Dihydroxybutan-2-yl 3-(4-(benzyloxy)phenyl)-2-((tert-butoxycarbonyl)aMino)propanoate;(S)-(2S,3R)-3,4-Dihydroxybutan-2-yl 3-(4-(benzyloxy)-phenyl)-2-((tert-butoxycarbonyl)amino)propan

Chemical Property of ERYTHRO-N-BOC-O-BENZYL-L-TYROSINE EPOXIDE

Chemical Property:

• Boiling Point: 528.5±35.0 °C(Predicted)
• PKA: 12.04±0.46(Predicted)
• PSA: 60.09000
• Density: 1.153±0.06 g/cm3(Predicted)
• LogP: 4.49110
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

(S)-(2S,3R)-3,4-Dihydroxybutan-2-yl 3-(4-(benzyloxy)-phenyl)-2-((tert-butoxycarbonyl)amino)propanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ERYTHRO-N-BOC-O-BENZYL-L-TYROSINE EPOXIDE

There total 3 articles about ERYTHRO-N-BOC-O-BENZYL-L-TYROSINE EPOXIDE 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:

(2S,3S)-N-tert-butoxycarbonyl-3-amino-4-(4-benzyloxyphenyl)-1-chloro-2-hydroxybutane (174801-33-3,1059189-63-7) → tert-butyl (1S)-2-[4-(benzyloxy)phenyl]-1-[(2S)-oxiranyl]ethylcarbamate (162536-84-7)

Guidance literature:

With potassium hydroxide; In ethanol;

DOI:10.1016/j.bmcl.2005.05.129

Reference yield:

ethyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-O-(phenylmethyl)-L-tyrosinate (127132-32-5) → tert-butyl (1S)-2-[4-(benzyloxy)phenyl]-1-[(2S)-oxiranyl]ethylcarbamate (162536-84-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / LDA / tetrahydrofuran / -78 °C

2: NaBH₄ / ethanol; tetrahydrofuran

3: KOH / ethanol

With potassium hydroxide; sodium tetrahydroborate; lithium diisopropyl amide; In tetrahydrofuran; ethanol;

DOI:10.1016/j.bmcl.2005.05.129

Reference yield:

(S)-N-[3-Chloro-2-oxo-1-[[4-(phenylmethoxy)phenyl]methyl]propyl]carbamic acid 1,1-dimethylethyl ester (152438-62-5) → tert-butyl (1S)-2-[4-(benzyloxy)phenyl]-1-[(2S)-oxiranyl]ethylcarbamate (162536-84-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / ethanol; tetrahydrofuran

2: KOH / ethanol

With potassium hydroxide; sodium tetrahydroborate; In tetrahydrofuran; ethanol;

DOI:10.1016/j.bmcl.2005.05.129

upstream raw materials:

(2S,3S)-N-tert-butoxycarbonyl-3-amino-4-(4-benzyloxyphenyl)-1-chloro-2-hydroxybutane

ethyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-O-(phenylmethyl)-L-tyrosinate

(S)-N-[3-Chloro-2-oxo-1-[[4-(phenylmethoxy)phenyl]methyl]propyl]carbamic acid 1,1-dimethylethyl ester

Downstream raw materials:

tert-butyl (1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-(isobutylamino)propylcarbamate

(2S,3S)-N-tert-butoxycarbonyl-3-amino-1,2-epoxy-4-(4-hydroxyphenyl)butane

(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-(4-{4-[(tert-butoxycarbonyl)amino]butoxy}benzyl)-2-hydroxypropylcarbamate

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-(4-{3-[(tert-butoxycarbonyl)amino]propoxy}benzyl)-2-hydroxypropylcarbamate

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