S-Phenyl (2S,3S)-2-<(1R)-hydroxyethyl)>-3-N-p-methoxybenzylamino-5-trimethylsilyl-4-pentynethioate

Base Information

• Chemical Name: S-Phenyl (2S,3S)-2-<(1R)-hydroxyethyl)>-3-N-p-methoxybenzylamino-5-trimethylsilyl-4-pentynethioate
• CAS No.: 121651-93-2
• Molecular Formula: C₂₄H₃₁NO₃SSi
• Molecular Weight: 441.667
• Mol file: 121651-93-2.mol

Synonyms:S-Phenyl (2S,3S)-2-<(1R)-hydroxyethyl)>-3-N-p-methoxybenzylamino-5-trimethylsilyl-4-pentynethioate

Chemical Property of S-Phenyl (2S,3S)-2-<(1R)-hydroxyethyl)>-3-N-p-methoxybenzylamino-5-trimethylsilyl-4-pentynethioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of S-Phenyl (2S,3S)-2-<(1R)-hydroxyethyl)>-3-N-p-methoxybenzylamino-5-trimethylsilyl-4-pentynethioate

There total 4 articles about S-Phenyl (2S,3S)-2-<(1R)-hydroxyethyl)>-3-N-p-methoxybenzylamino-5-trimethylsilyl-4-pentynethioate 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: 60.0%

(R)-3-hydroxybutyric acid (625-72-9,26063-00-3,29435-48-1) → (2S,3S)-2-((R)-1-Hydroxy-ethyl)-3-(4-methoxy-benzylamino)-5-trimethylsilanyl-pent-4-ynethioic acid S-phenyl ester (108053-20-9,121651-93-2,131900-51-1)

Guidance literature:

DOI:10.1021/jo00294a002

Reference yield:

3-(trimethylsilyl)prop-2-yn-1-al (2975-46-4) → S-Phenyl (2S,3S)-2-<(1R)-hydroxyethyl)>-3-N-p-methoxybenzylamino-5-trimethylsilyl-4-pentynethioate (121651-93-2)

Guidance literature:

Multi-step reaction with 2 steps

1: MgSO₄ / diethyl ether / 0.5 h / Ambient temperature

2: 1.) 9-borabicyclo<3.3.1>non-9-yl triflate, diisopropylethylamine / 1.) CH₂Cl₂, -78 deg C, 10 min, then -30 deg C, 2 h, 2.) -50 to -30 deg C gradually, then 2 h

With magnesium sulfate; N-ethyl-N,N-diisopropylamine; 9-BBN triflate; In diethyl ether;

DOI:10.1016/S0040-4020(01)87042-3

Reference yield:

4-methoxy-benzylamine (2393-23-9) → S-Phenyl (2S,3S)-2-<(1R)-hydroxyethyl)>-3-N-p-methoxybenzylamino-5-trimethylsilyl-4-pentynethioate (121651-93-2)

Guidance literature:

Multi-step reaction with 2 steps

1: MgSO₄ / diethyl ether / 0.5 h / Ambient temperature

2: 1.) 9-borabicyclo<3.3.1>non-9-yl triflate, diisopropylethylamine / 1.) CH₂Cl₂, -78 deg C, 10 min, then -30 deg C, 2 h, 2.) -50 to -30 deg C gradually, then 2 h

With magnesium sulfate; N-ethyl-N,N-diisopropylamine; 9-BBN triflate; In diethyl ether;

DOI:10.1016/S0040-4020(01)87042-3

upstream raw materials:

(R)-3-hydroxybutyric acid

(R)-3-hydroxybutyrate thiophenyl ester

(4-Methoxy-benzyl)-[3-trimethylsilanyl-prop-2-yn-(Z)-ylidene]-amine

3-(trimethylsilyl)prop-2-yn-1-al

Downstream raw materials:

(3R,4R)-4-Ethynyl-3-((S)-1-hydroxy-ethyl)-1-(4-methoxy-benzyl)-azetidin-2-one

(3S,4S)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-4-phenylsulfanylethynyl-azetidin-2-one

(3S,4S)-4-Ethynyl-3-<(1R)-hydroxyethyl>-N-p-methoxybenzyl-2-azetidinone

(3S,4S)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-4-trimethylsilanylethynyl-azetidin-2-one