methyl (S)-3-(benzo[b]thiophen-3-yl)-2-(benzyloxycarbonylamino)propanoate

Base Information

• Chemical Name: methyl (S)-3-(benzo[b]thiophen-3-yl)-2-(benzyloxycarbonylamino)propanoate
• CAS No.: 1379685-76-3
• Molecular Formula: C₂₀H₁₉NO₄S
• Molecular Weight: 369.441

Synonyms:methyl (S)-3-(benzo[b]thiophen-3-yl)-2-(benzyloxycarbonylamino)propanoate

Chemical Property of methyl (S)-3-(benzo[b]thiophen-3-yl)-2-(benzyloxycarbonylamino)propanoate

Chemical Property:

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Technology Process of methyl (S)-3-(benzo[b]thiophen-3-yl)-2-(benzyloxycarbonylamino)propanoate

There total 2 articles about methyl (S)-3-(benzo[b]thiophen-3-yl)-2-(benzyloxycarbonylamino)propanoate 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: 94.0%

C20H17NO4S (1379685-75-2) → methyl (S)-3-(benzo[b]thiophen-3-yl)-2-(benzyloxycarbonylamino)propanoate (1379685-76-3)

Guidance literature:

With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; at 70 ℃; for 15h; under 15001.5 Torr; optical yield given as %ee; enantioselective reaction;

DOI:10.1016/j.tetlet.2012.04.055

Reference yield:

benzothiophene-3-carboxaldehyde (5381-20-4) → methyl (S)-3-(benzo[b]thiophen-3-yl)-2-(benzyloxycarbonylamino)propanoate (1379685-76-3)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N,N',N'-tetramethylguanidine / dichloromethane / 3.5 h / -30 - 20 °C

2: bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / 15 h / 70 °C / 15001.5 Torr

With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; N,N,N',N'-tetramethylguanidine; In dichloromethane; 1: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetlet.2012.04.055

Reference yield: 100.0%

methyl (S)-3-(benzo[b]thiophen-3-yl)-2-(benzyloxycarbonylamino)propanoate (1379685-76-3) → C19H19NO3S (1379685-77-4)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; methanol; at 20 ℃; for 5h;

DOI:10.1016/j.tetlet.2012.04.055

upstream raw materials:

benzothiophene-3-carboxaldehyde

C₂₀H₁₇NO₄S

Downstream raw materials:

C₁₉H₁₉NO₃S

C₂₀H₁₄F₃NO₂S

C₂₀H₁₇NO₃S

C₁₉H₁₄N₂O₄S

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