2(S)-<(tert-butoxycarbonyl)amino>-3-<4-(phenylmethoxy)phenyl>-1-(phenylsulfonyl)propane

Base Information

• Chemical Name: 2(S)-<(tert-butoxycarbonyl)amino>-3-<4-(phenylmethoxy)phenyl>-1-(phenylsulfonyl)propane
• CAS No.: 108385-54-2
• Molecular Formula: C₂₇H₃₁NO₅S
• Molecular Weight: 481.613
• Mol file: 108385-54-2.mol

Synonyms:2(S)-<(tert-butoxycarbonyl)amino>-3-<4-(phenylmethoxy)phenyl>-1-(phenylsulfonyl)propane

Chemical Property of 2(S)-<(tert-butoxycarbonyl)amino>-3-<4-(phenylmethoxy)phenyl>-1-(phenylsulfonyl)propane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(S)-<(tert-butoxycarbonyl)amino>-3-<4-(phenylmethoxy)phenyl>-1-(phenylsulfonyl)propane

There total 5 articles about 2(S)-<(tert-butoxycarbonyl)amino>-3-<4-(phenylmethoxy)phenyl>-1-(phenylsulfonyl)propane 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: 91.0%

2(S)-<(tert-butoxycarbonyl)amino>-1-(phenylthio)-3-<4-(phenylmethoxy)phenyl>propane (109687-71-0) → 2(S)-<(tert-butoxycarbonyl)amino>-3-<4-(phenylmethoxy)phenyl>-1-(phenylsulfonyl)propane (108385-54-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 25 ℃; for 1h;

DOI:10.1021/jo00226a007

Reference yield:

O-benzyl N-Boc-L-tyrosinol (66605-58-1) → 2(S)-<(tert-butoxycarbonyl)amino>-3-<4-(phenylmethoxy)phenyl>-1-(phenylsulfonyl)propane (108385-54-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / triethylamine / CH₂Cl₂ / 0.33 h / 0 °C

2: 1.) NaOCH₃ / 1.) THF, MeOH, 25 deg C, 0.25 h, 2.) THF, MeOH, 50 deg C, 2.5 h

3: 91 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 1 h / 25 °C

With sodium methylate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jo00226a007

Reference yield:

2(S)-<(tert-butoxycarbinol)amino>-1-<(methylsulfonyl)oxy>-3-<-4-(phenylmethoxy)phenyl>propane (109687-67-4) → 2(S)-<(tert-butoxycarbonyl)amino>-3-<4-(phenylmethoxy)phenyl>-1-(phenylsulfonyl)propane (108385-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaOCH₃ / 1.) THF, MeOH, 25 deg C, 0.25 h, 2.) THF, MeOH, 50 deg C, 2.5 h

2: 91 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 1 h / 25 °C

With sodium methylate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jo00226a007

upstream raw materials:

2(S)-<(tert-butoxycarbonyl)amino>-1-(phenylthio)-3-<4-(phenylmethoxy)phenyl>propane

O-benzyl N-Boc-L-tyrosinol

2(S)-<(tert-butoxycarbinol)amino>-1-<(methylsulfonyl)oxy>-3-<-4-(phenylmethoxy)phenyl>propane

sodium thiophenolate

Downstream raw materials:

5(S)-<(tert-butoxycarbonyl)amino>-2(R)-methyl-6-<4-(phenylmethoxy)phenyl>-trans-3-hexenoic acid

5(S)-<(tert-butoxycarbonyl)amino>-2(R)-methyl-6-<4-(phenylmethoxy)phenyl>-1-<(2-tetrahydropyranyl)oxy>-trans-3-hexene

(E)-(S)-6-(4-Benzyloxy-phenyl)-5-tert-butoxycarbonylamino-2-methyl-hex-3-enoic acid

[(E)-(S)-1-(4-Benzyloxy-benzyl)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-2-enyl]-carbamic acid tert-butyl ester