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

Base Information

• Chemical Name: (2S,3S)-3-(tert-butoxycarbonylamino)-5-phenyl-1-(2-naphthylthio)-2-pentanol
• CAS No.: 799560-01-3
• Molecular Formula: C₂₆H₃₁NO₃S
• Molecular Weight: 437.603
• Mol file: 799560-01-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (2S,3S)-3-(tert-butoxycarbonylamino)-5-phenyl-1-(2-naphthylthio)-2-pentanol 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: 87.0%

2-Naphthalenethiol (91-60-1) + (S)-[(S)-1-(tert-butoxycarbonylamino)-3-phenylpropyl]oxirane (799559-75-4,1217728-66-9) → (2S,3S)-3-(tert-butoxycarbonylamino)-5-phenyl-1-(2-naphthylthio)-2-pentanol (799560-01-3)

Guidance literature:

With triethylamine; In methanol; for 4h; Heating;

DOI:10.1021/jo0268456

Reference yield:

(2R,3R)-trans-2,3-epoxy-5-phenyl-1-pentanol (154428-47-4) → (2S,3S)-3-(tert-butoxycarbonylamino)-5-phenyl-1-(2-naphthylthio)-2-pentanol (799560-01-3)

Guidance literature:

Multi-step reaction with 4 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

4: 87 percent / Et₃N / methanol / 4 h / Heating

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

DOI:10.1021/jo0268456

Reference yield:

(2S,3S)-3-diphenylmethylamino-5-phenyl-1,2-pentanediol (154079-56-8) → (2S,3S)-3-(tert-butoxycarbonylamino)-5-phenyl-1-(2-naphthylthio)-2-pentanol (799560-01-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / H₂ / Pd(OH)2/C / ethyl acetate / 20 °C

2: 92 percent / Ph₃P; diisopropyl azodicarboxylate / CHCl₃ / 20 h / Heating

3: 87 percent / Et₃N / methanol / 4 h / Heating

With di-isopropyl azodicarboxylate; hydrogen; triethylamine; triphenylphosphine; palladium dihydroxide; In methanol; chloroform; ethyl acetate; 2: Mitsunobu cyclization;

DOI:10.1021/jo0268456

upstream raw materials:

2-Naphthalenethiol

(S)-[(S)-1-(tert-butoxycarbonylamino)-3-phenylpropyl]oxirane

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

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

Downstream raw materials:

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

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