methyl (2R,3S)-3-(acetylthio)-2-((tert-butoxycarbonyl)amino)-3-phenylpropionate

Base Information

Chemical Name:methyl (2R,3S)-3-(acetylthio)-2-((tert-butoxycarbonyl)amino)-3-phenylpropionate
CAS No.:136620-77-4
Molecular Formula:C₁₇H₂₃NO₅S
Molecular Weight:353.439
Hs Code.:

Synonyms:methyl (2R,3S)-3-(acetylthio)-2-((tert-butoxycarbonyl)amino)-3-phenylpropionate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl (2R,3S)-3-(acetylthio)-2-((tert-butoxycarbonyl)amino)-3-phenylpropionate

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Technology Process of methyl (2R,3S)-3-(acetylthio)-2-((tert-butoxycarbonyl)amino)-3-phenylpropionate

There total 8 articles about methyl (2R,3S)-3-(acetylthio)-2-((tert-butoxycarbonyl)amino)-3-phenylpropionate 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: 87.0%

: 136620-76-3
methyl (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-((methanesulfonyl)oxy)-3-phenylpropionate

: 63658-17-3,63658-18-4,63096-26-4
methyl 2-(tert-butoxycarbonylamino)-3-phenylacrylate

: 136620-77-4
methyl (2R,3S)-3-(acetylthio)-2-((tert-butoxycarbonyl)amino)-3-phenylpropionate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; tiolacetic acid; In N,N-dimethyl-formamide; for 30h; Ambient temperature;
DOI:10.1021/jo00038a048

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 136620-77-4
methyl (2R,3S)-3-(acetylthio)-2-((tert-butoxycarbonyl)amino)-3-phenylpropionate

Guidance literature:: Multi-step reaction with 5 steps

2: H₂O₂, HCOOH

3: 1) 2N aq. LiOH / 1) dioxane, RT, overnight, 2a) Et₂O, 0 deg C, 15 min, 2b) RT, 30 min

4: NEt₃ / CH₂Cl₂ / 0.75 h / 0 °C

5: 87 percent / DBU, thiolacetic acid / dimethylformamide / 30 h / Ambient temperature

With lithium hydroxide; formic acid; dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; tiolacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00038a048

Reference yield:

: 100-52-7
benzaldehyde

: 136620-77-4
methyl (2R,3S)-3-(acetylthio)-2-((tert-butoxycarbonyl)amino)-3-phenylpropionate

Guidance literature:: Multi-step reaction with 7 steps

1: 1) Sn(OTf)2, NEt₃

4: H₂O₂, HCOOH

5: 1) 2N aq. LiOH / 1) dioxane, RT, overnight, 2a) Et₂O, 0 deg C, 15 min, 2b) RT, 30 min

6: NEt₃ / CH₂Cl₂ / 0.75 h / 0 °C

7: 87 percent / DBU, thiolacetic acid / dimethylformamide / 30 h / Ambient temperature

With lithium hydroxide; tin(II) trifluoromethanesulfonate; formic acid; dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; tiolacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00038a048