L-Proline, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-(2S,3S)-3-amino-2-(phenylsel eno)butanoyl-, 2-(trimethylsilyl)ethyl ester

Base Information

• Chemical Name: L-Proline, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-(2S,3S)-3-amino-2-(phenylsel eno)butanoyl-, 2-(trimethylsilyl)ethyl ester
• CAS No.: 190598-42-6
• Molecular Formula: C₂₈H₄₅N₃O₆SeSi
• Molecular Weight: 626.727
• Mol file: 190598-42-6.mol

Synonyms:

Chemical Property of L-Proline, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-(2S,3S)-3-amino-2-(phenylsel eno)butanoyl-, 2-(trimethylsilyl)ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Proline, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-(2S,3S)-3-amino-2-(phenylsel eno)butanoyl-, 2-(trimethylsilyl)ethyl ester

There total 5 articles about L-Proline, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-(2S,3S)-3-amino-2-(phenylsel eno)butanoyl-, 2-(trimethylsilyl)ethyl 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:

L-N-Boc-Ala (15761-38-3) + (S)-1-((2S,3S)-3-Amino-2-phenylselanyl-butyryl)-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester → (S)-1-[(2S,3S)-3-((S)-2-tert-Butoxycarbonylamino-propionylamino)-2-phenylselanyl-butyryl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester (190598-42-6)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 ℃; Yield given;

DOI:10.1016/S0040-4039(97)00612-6

Reference yield:

Phenylselenyl bromide (34837-55-3) → (S)-1-[(2S,3S)-3-((S)-2-tert-Butoxycarbonylamino-propionylamino)-2-phenylselanyl-butyryl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester (190598-42-6)

Guidance literature:

Multi-step reaction with 5 steps

3: 40 percent / PyBOP, DIPEA / acetonitrile / -78 - 0 °C

4: 4 N HCl / dioxane

5: TBTU, DIPEA / acetonitrile / 0 °C

With hydrogenchloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; acetonitrile;

DOI:10.1016/S0040-4039(97)00612-6

Reference yield:

(2S,3S)-3-tert-Butoxycarbonylamino-2-phenylselanyl-butyric acid (190598-38-0) → (S)-1-[(2S,3S)-3-((S)-2-tert-Butoxycarbonylamino-propionylamino)-2-phenylselanyl-butyryl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester (190598-42-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 40 percent / PyBOP, DIPEA / acetonitrile / -78 - 0 °C

2: 4 N HCl / dioxane

3: TBTU, DIPEA / acetonitrile / 0 °C

With hydrogenchloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; acetonitrile;

DOI:10.1016/S0040-4039(97)00612-6

upstream raw materials:

L-N-Boc-Ala

Phenylselenyl bromide

(2S,3S)-3-tert-Butoxycarbonylamino-2-phenylselanyl-butyric acid

(S)-1-((2S,3S)-3-tert-Butoxycarbonylamino-2-phenylselanyl-butyryl)-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

Downstream raw materials:

(S)-1-{(2S,3S)-2-Phenylselanyl-3-[(S)-2-(2,2,2-trifluoro-acetylamino)-propionylamino]-butyryl}-pyrrolidine-2-carboxylic acid ((S)-1-dimethylcarbamoyl-2-methyl-propyl)-amide

((S)-1-{(1S,2S)-3-[(S)-2-((S)-1-Dimethylcarbamoyl-2-methyl-propylcarbamoyl)-pyrrolidin-1-yl]-1-methyl-3-oxo-2-phenylselanyl-propylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester