(E)-(2S,3R)-2-((S)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenylsulfanyl-pent-4-enoic acid tert-butyl ester

Base Information

• Chemical Name: (E)-(2S,3R)-2-((S)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenylsulfanyl-pent-4-enoic acid tert-butyl ester
• CAS No.: 112020-68-5
• Molecular Formula: C₁₉H₂₇NO₅S
• Molecular Weight: 381.493
• Mol file: 112020-68-5.mol

Synonyms:(E)-(2S,3R)-2-((S)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenylsulfanyl-pent-4-enoic acid tert-butyl ester

Chemical Property of (E)-(2S,3R)-2-((S)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenylsulfanyl-pent-4-enoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,3R)-2-((S)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenylsulfanyl-pent-4-enoic acid tert-butyl ester

There total 2 articles about (E)-(2S,3R)-2-((S)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenylsulfanyl-pent-4-enoic 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:

tert-butyl (R)-3-hydroxybutanoate (110171-06-7) + N-methoxycarbonyl (2-phenylthio)ethenylcarboxaldimine (111970-53-7) → (E)-(R)-2-((R)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenylsulfanyl-pent-4-enoic acid tert-butyl ester (111197-09-2,111266-21-8,112020-63-0,112020-68-5,112020-72-1,112020-75-4,132958-18-0,132958-19-1)

Guidance literature:

With lithium diisopropyl amide; Multistep reaction; 1) THF, -78 to -40 deg C, 1 h, 2) THF, -78 deg C, 1 h;

DOI:10.1016/S0040-4039(00)95651-X

Reference yield:

tert-butyl (S)-3-hydroxybutyrate (82578-45-8) + [(E)-3-Phenylsulfanyl-prop-2-en-(Z)-ylidene]-carbamic acid methyl ester (111197-06-9,111970-53-7,132828-50-3) → (E)-(2S,3R)-2-((S)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenylsulfanyl-pent-4-enoic acid tert-butyl ester (112020-68-5) + (E)-(2S,3S)-2-((S)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenylsulfanyl-pent-4-enoic acid tert-butyl ester (112020-63-0)

Guidance literature:

With lithium chloride; lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, -78 to -50 deg C;

Reference yield: 71.0%

(E)-(2S,3R)-2-((S)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenylsulfanyl-pent-4-enoic acid tert-butyl ester (112020-68-5) → (2S,3S,4S)-4-Methoxycarbonylamino-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-carboxylic acid tert-butyl ester (132894-53-2,132894-61-2)

Guidance literature:

With hydrogenchloride; In dichloromethane; at 0 ℃; for 12h;

upstream raw materials:

tert-butyl (S)-3-hydroxybutyrate

[(E)-3-Phenylsulfanyl-prop-2-en-(Z)-ylidene]-carbamic acid methyl ester

tert-butyl (R)-3-hydroxybutanoate

N-methoxycarbonyl (2-phenylthio)ethenylcarboxaldimine

Downstream raw materials:

(2S,3S,4S)-4-Methoxycarbonylamino-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-carboxylic acid tert-butyl ester

methyl-3-amino-2,3,6-tridesoxy-α-L-arabino-hexopyranoside

methyl 3-benzamido-2,3,6-trideoxy-α-L-arabino-hexopyranoside

C₁₇H₂₀ClNO₈