[(1S,2S)-1-Benzyl-3-chloro-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(1S,2S)-1-Benzyl-3-chloro-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester
• CAS No.: 357604-38-7
• Molecular Formula: C₂₀H₃₀ClNO₄
• Molecular Weight: 383.916

Synonyms:[(1S,2S)-1-Benzyl-3-chloro-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester

Chemical Property of [(1S,2S)-1-Benzyl-3-chloro-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of [(1S,2S)-1-Benzyl-3-chloro-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester

There total 3 articles about [(1S,2S)-1-Benzyl-3-chloro-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester 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:

2(R)-((tert-butyloxycarbonyl)amino)-1,4-dichloro-3(S)-hydroxybutane (326479-99-6) → [(1S,2S)-1-Benzyl-3-chloro-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester (357604-38-7)

Guidance literature:

Multi-step reaction with 3 steps

1: p-TsOH*H₂O / CH₂Cl₂

2: NaH / tetrahydrofuran

3: CuBr*SMe₂ / tetrahydrofuran

With copper(I) bromide dimethylsulfide complex; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol016147s

Reference yield:

[(1R,2S)-3-Chloro-1-chloromethyl-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester (357604-36-5) → [(1S,2S)-1-Benzyl-3-chloro-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester (357604-38-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / tetrahydrofuran

2: CuBr*SMe₂ / tetrahydrofuran

With copper(I) bromide dimethylsulfide complex; sodium hydride; In tetrahydrofuran;

DOI:10.1021/ol016147s

Reference yield:

phenyllithium (591-51-5) + (S)-2-[(S)-2-Chloro-1-(tetrahydro-pyran-2-yloxy)-ethyl]-aziridine-1-carboxylic acid tert-butyl ester (357604-37-6) → [(1S,2S)-1-Benzyl-3-chloro-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester (357604-38-7)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran;

DOI:10.1021/ol016147s

upstream raw materials:

phenyllithium

(S)-2-[(S)-2-Chloro-1-(tetrahydro-pyran-2-yloxy)-ethyl]-aziridine-1-carboxylic acid tert-butyl ester

2(R)-((tert-butyloxycarbonyl)amino)-1,4-dichloro-3(S)-hydroxybutane

[(1R,2S)-3-Chloro-1-chloromethyl-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester

Downstream raw materials:

4-nitro-N-((2R(syn),3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzenesulfonamide

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

amprenavir

(2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol

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