tert-butyl (S)-1-((S)-2-((S)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl (S)-1-((S)-2-((S)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate
• CAS No.: 1387565-14-1
• Molecular Formula: C₃₃H₄₈N₃O₇PS₂
• Molecular Weight: 693.866

Synonyms:tert-butyl (S)-1-((S)-2-((S)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

Chemical Property of tert-butyl (S)-1-((S)-2-((S)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

Chemical Property:

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Technology Process of tert-butyl (S)-1-((S)-2-((S)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

There total 10 articles about tert-butyl (S)-1-((S)-2-((S)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate 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: 27.0%

t-Boc-L-valine (13734-41-3) + (2S)-bis(4-(methylthio)phenyl) 2-methyl-1-(pyrrolidine-2-carboxamido)propylphosphonate trifluoroacetate → tert-butyl (S)-1-((S)-2-((R)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (1387564-76-2) + tert-butyl (S)-1-((S)-2-((S)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (1387565-14-1)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃;

DOI:10.1021/acsmedchemlett.7b00533

Reference yield: 17.0%

tert-butyl (S)-1-((S)-2-((R,S)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate → tert-butyl (S)-1-((S)-2-((R)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (1387564-76-2) + tert-butyl (S)-1-((S)-2-((S)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (1387565-14-1)

Guidance literature:

Resolution of racemate;

DOI:10.1021/jm300599x

Reference yield:

(2S)-tert-butyl 2-(1-(bis(4-(methylthio)phenoxy)phosphoryl)-2-methylpropylcarbamoyl)pyrrolidine-1-carboxylate → tert-butyl (S)-1-((S)-2-((R)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (1387564-76-2) + tert-butyl (S)-1-((S)-2-((S)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (1387565-14-1)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 2 h / 20 °C

2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / acetonitrile / 20 °C

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;

DOI:10.1021/acsmedchemlett.7b00533

upstream raw materials:

tris(4-(methylthio)phenyl) phosphite

4-hydroxythioanisole

t-Boc-L-valine

benzyl 1-(bis(4-(methylthio)phenoxy)phosphoryl)-2-methylpropylcarbamate

Downstream raw materials:

bis(4-(methylthio)phenyl) (S)-1-((S)-1-((S)-2-(4-methoxybenzamido)-3-methylbutanoyl)pyrrolidine-2-carboxamido)-2-methylpropylphosphonate

tert-butyl 2-(4-(2-((S)-1-((S)-2-((S)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-2-oxoethoxy)phenoxy)acetate

2-(4-(2-((S)-1-((S)-2-((S)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-2-oxoethoxy)phenoxy)acetic acid

tert-butyl 2-(3-(2-((S)-1-((S)-2-((S)-1-(bis(4-(methylthio)phenoxy)-phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-2-oxoethyl)-2,6-dioxo-2,3-dihydropyrimidin-1(6H)-yl)acetate

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