(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3S)-2-hydroxy-3-{[N-(methylsulfonyl)-S-(naphthalen-2-yl)-D-cysteinyl]amino}-4-phenylbutyl]decahydroisoquinoline-3-carboxamide

Base Information

• Chemical Name: (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3S)-2-hydroxy-3-{[N-(methylsulfonyl)-S-(naphthalen-2-yl)-D-cysteinyl]amino}-4-phenylbutyl]decahydroisoquinoline-3-carboxamide
• CAS No.: 159878-29-2
• Molecular Formula: C38H52 N4 O5 S2
• Molecular Weight: 708.9733
• Mol file: 159878-29-2.mol

Synonyms:

Chemical Property of (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3S)-2-hydroxy-3-{[N-(methylsulfonyl)-S-(naphthalen-2-yl)-D-cysteinyl]amino}-4-phenylbutyl]decahydroisoquinoline-3-carboxamide

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.27g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3S)-2-hydroxy-3-{[N-(methylsulfonyl)-S-(naphthalen-2-yl)-D-cysteinyl]amino}-4-phenylbutyl]decahydroisoquinoline-3-carboxamide

There total 6 articles about (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3S)-2-hydroxy-3-{[N-(methylsulfonyl)-S-(naphthalen-2-yl)-D-cysteinyl]amino}-4-phenylbutyl]decahydroisoquinoline-3-carboxamide 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:

N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane (128018-44-0) → (3S,4aS,8aS)-2-{(2R,3S)-2-Hydroxy-3-[(S)-2-methanesulfonylamino-3-(naphthalen-2-ylsulfanyl)-propionylamino]-4-phenyl-butyl}-decahydro-isoquinoline-3-carboxylic acid tert-butylamide (159878-29-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 60.3 percent / propan-2-ol / 5 h / Heating

2.1: m-cresol; thioanisole; 1,2-ethanedithiol / TFA; TMSBr / 2 h / 0 °C

3.1: HOBt; BOP; DIPEA / dimethylformamide / 0.17 h / 0 °C

3.2: Et₃N / dimethylformamide / 0 - 20 °C

4.1: HCl / dioxane / 0 - 20 °C

5.1: DIPEA / dimethylformamide / 0 - 20 °C

With hydrogenchloride; methyl-phenyl-thioether; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; ethane-1,2-dithiol; 3-methyl-phenol; N-ethyl-N,N-diisopropylamine; trimethylsilyl bromide; trifluoroacetic acid; In 1,4-dioxane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm020537i

Reference yield:

(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide (128019-40-9,149510-73-6,136465-81-1,168899-60-3) → (3S,4aS,8aS)-2-{(2R,3S)-2-Hydroxy-3-[(S)-2-methanesulfonylamino-3-(naphthalen-2-ylsulfanyl)-propionylamino]-4-phenyl-butyl}-decahydro-isoquinoline-3-carboxylic acid tert-butylamide (159878-29-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 60.3 percent / propan-2-ol / 5 h / Heating

2.1: m-cresol; thioanisole; 1,2-ethanedithiol / TFA; TMSBr / 2 h / 0 °C

3.1: HOBt; BOP; DIPEA / dimethylformamide / 0.17 h / 0 °C

3.2: Et₃N / dimethylformamide / 0 - 20 °C

4.1: HCl / dioxane / 0 - 20 °C

5.1: DIPEA / dimethylformamide / 0 - 20 °C

With hydrogenchloride; methyl-phenyl-thioether; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; ethane-1,2-dithiol; 3-methyl-phenol; N-ethyl-N,N-diisopropylamine; trimethylsilyl bromide; trifluoroacetic acid; In 1,4-dioxane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm020537i

Reference yield:

2-<3(S)-(Benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide (137431-05-1) → (3S,4aS,8aS)-2-{(2R,3S)-2-Hydroxy-3-[(S)-2-methanesulfonylamino-3-(naphthalen-2-ylsulfanyl)-propionylamino]-4-phenyl-butyl}-decahydro-isoquinoline-3-carboxylic acid tert-butylamide (159878-29-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: m-cresol; thioanisole; 1,2-ethanedithiol / TFA; TMSBr / 2 h / 0 °C

2.1: HOBt; BOP; DIPEA / dimethylformamide / 0.17 h / 0 °C

2.2: Et₃N / dimethylformamide / 0 - 20 °C

3.1: HCl / dioxane / 0 - 20 °C

4.1: DIPEA / dimethylformamide / 0 - 20 °C

With hydrogenchloride; methyl-phenyl-thioether; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; ethane-1,2-dithiol; 3-methyl-phenol; N-ethyl-N,N-diisopropylamine; trimethylsilyl bromide; trifluoroacetic acid; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jm020537i

upstream raw materials:

methanesulfonyl chloride

(3S,4aS,8aS)-2-{(2R,3S)-3-[(S)-2-Amino-3-(naphthalen-2-ylsulfanyl)-propionylamino]-2-hydroxy-4-phenyl-butyl}-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane

(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide

Downstream raw materials:

(3S,4aS,8aS)-2-{(2R,3S)-2-Hydroxy-3-[(S)-2-methanesulfonylamino-3-(naphthalene-2-sulfinyl)-propionylamino]-4-phenyl-butyl}-decahydro-isoquinoline-3-carboxylic acid tert-butylamide