ERYTHRO-N-BOC-L-HOMOPHENYLALANINE EPOXIDE

Base Information

• Chemical Name: ERYTHRO-N-BOC-L-HOMOPHENYLALANINE EPOXIDE
• CAS No.: 799559-75-4
• Molecular Formula: C16H23NO3
• Molecular Weight: 277.36

Synonyms:(2S,3S)-3-[(t-Butoxycarbonyl)amino]-5-phenyl-1,2-epoxypentane;tert-butyl (S)-1-((S)-oxiran-2-yl)-3-phenylpropylcarbamate;

Chemical Property of ERYTHRO-N-BOC-L-HOMOPHENYLALANINE EPOXIDE

Chemical Property:

• PSA: 50.86000
• LogP: 3.30220

Purity/Quality:

97% ^*data from raw suppliers

erythro-N-Boc-L-homophenylalanine epoxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ERYTHRO-N-BOC-L-HOMOPHENYLALANINE EPOXIDE

There total 4 articles about ERYTHRO-N-BOC-L-HOMOPHENYLALANINE 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: 98.5%

tert-butyl (S)-1-((S)-oxiran-2-yl)-3-phenylprop-2-ynylcarbamate (1174892-63-7) → (S)-[(S)-1-(tert-butoxycarbonylamino)-3-phenylpropyl]oxirane (799559-75-4,1217728-66-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 0.333333h;

DOI:10.1021/jo900643b

Reference yield: 92.0%

(2S,3S)-3-(tert-butoxycarbonylamino)-5-phenyl-1,2-pentanediol (154079-57-9) → (S)-[(S)-1-(tert-butoxycarbonylamino)-3-phenylpropyl]oxirane (799559-75-4,1217728-66-9)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In chloroform; for 20h; Heating;

DOI:10.1021/jo0268456

Reference yield:

(2R,3R)-trans-2,3-epoxy-5-phenyl-1-pentanol (154428-47-4) → (S)-[(S)-1-(tert-butoxycarbonylamino)-3-phenylpropyl]oxirane (799559-75-4,1217728-66-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / Ti(O-i-Pr)4 / CH₂Cl₂ / 20 °C

2: 93 percent / H₂ / Pd(OH)2/C / ethyl acetate / 20 °C

3: 92 percent / Ph₃P; diisopropyl azodicarboxylate / CHCl₃ / 20 h / Heating

With titanium(IV) isopropylate; di-isopropyl azodicarboxylate; hydrogen; triphenylphosphine; palladium dihydroxide; In dichloromethane; chloroform; ethyl acetate; 3: Mitsunobu cyclization;

DOI:10.1021/jo0268456

upstream raw materials:

(2S,3S)-3-(tert-butoxycarbonylamino)-5-phenyl-1,2-pentanediol

(2R,3R)-trans-2,3-epoxy-5-phenyl-1-pentanol

(2S,3S)-3-diphenylmethylamino-5-phenyl-1,2-pentanediol

tert-butyl (S)-1-((S)-oxiran-2-yl)-3-phenylprop-2-ynylcarbamate

Downstream raw materials:

tert-butyl (2S,3S)-2-hydroxy-5-phenyl-1-(phenylthio)pentan-3-ylcarbamate

(2S,3S)-3-(tert-butoxycarbonylamino)-5-phenyl-1-(2-naphthylthio)-2-pentanol

(2S,3S)-3-(tert-butoxycarbonylamino)-5-phenyl-1-(2-naphthylsulfonyl)-2-pentanol

(2S,3S)-3-(tert-butoxycarbonylamino)-5-phenyl-1-phenylsulfonyl-2-pentanol

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