(2S,3R)-3-(3-{(R)-1-[(S)-amino-(tert-butoxycarbonylmethylcarbamoyl)methyl]-1-methylprop-2-ynyloxy}-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

Base Information

• Chemical Name: (2S,3R)-3-(3-{(R)-1-[(S)-amino-(tert-butoxycarbonylmethylcarbamoyl)methyl]-1-methylprop-2-ynyloxy}-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester
• CAS No.: 870137-23-8
• Molecular Formula: C₄₁H₅₁N₃O₁₀
• Molecular Weight: 745.87

Synonyms:(2S,3R)-3-(3-{(R)-1-[(S)-amino-(tert-butoxycarbonylmethylcarbamoyl)methyl]-1-methylprop-2-ynyloxy}-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

Chemical Property of (2S,3R)-3-(3-{(R)-1-[(S)-amino-(tert-butoxycarbonylmethylcarbamoyl)methyl]-1-methylprop-2-ynyloxy}-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-(3-{(R)-1-[(S)-amino-(tert-butoxycarbonylmethylcarbamoyl)methyl]-1-methylprop-2-ynyloxy}-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

There total 11 articles about (2S,3R)-3-(3-{(R)-1-[(S)-amino-(tert-butoxycarbonylmethylcarbamoyl)methyl]-1-methylprop-2-ynyloxy}-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl 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:

{[(2S,3S)-3-ethynyl-3-methyl-1-(2-nitrobenzenesulfonyl)-aziridine-2-carbonyl]amino}acetic acid tert-butyl ester (870137-16-9) → (2S,3R)-3-(3-{(R)-1-[(S)-amino-(tert-butoxycarbonylmethylcarbamoyl)methyl]-1-methylprop-2-ynyloxy}-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester (870137-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / CuOAc; DBU / toluene

2: 78 percent / PhSH; Cs₂CO₃ / dimethylformamide

With copper (I) acetate; caesium carbonate; thiophenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2006.06.071

Reference yield:

(2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester (870137-17-0) → (2S,3R)-3-(3-{(R)-1-[(S)-amino-(tert-butoxycarbonylmethylcarbamoyl)methyl]-1-methylprop-2-ynyloxy}-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester (870137-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / CuOAc; DBU / toluene

2: 78 percent / PhSH; Cs₂CO₃ / dimethylformamide

With copper (I) acetate; caesium carbonate; thiophenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2006.06.071

Reference yield:

(4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-3-hydroxy-2-methylaminopropionic acid methyl ester (821006-11-5) → (2S,3R)-3-(3-{(R)-1-[(S)-amino-(tert-butoxycarbonylmethylcarbamoyl)methyl]-1-methylprop-2-ynyloxy}-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester (870137-23-8)

Guidance literature:

Multi-step reaction with 5 steps

1: aq.LiOH

2: DBU

3: 90 percent / CuOAc; DBU / toluene / 2 h / 0 °C

4: 78 percent / PhSH; Cs₂CO₃ / dimethylformamide / 5 h / 20 °C

With lithium hydroxide; copper (I) acetate; caesium carbonate; thiophenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol052287g

upstream raw materials:

{[(2S,3S)-3-ethynyl-3-methyl-1-(2-nitrobenzenesulfonyl)-aziridine-2-carbonyl]amino}acetic acid tert-butyl ester

(2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

(4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-3-hydroxy-2-methylaminopropionic acid methyl ester

(4S,5R)-5-(3-acetoxy-4-benzyloxyphenyl)-2-(4-methoxyphenyl)-3-methyloxazolidine-4-carboxylic acid methyl ester

Downstream raw materials:

(2S,3R)-3-(3-{(R)-1-[(S)-((S)-2-Amino-propionylamino)-(tert-butoxycarbonylmethyl-carbamoyl)-methyl]-1-methyl-propoxy}-4-hydroxy-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-propionic acid

(2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-((S)-2-benzyloxycarbonylamino-4-methylpentyrylamino)-(tert-butoxycarbonylmethylcarbamoyl)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

(2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-((S)-2-benzyloxycarbonylamino-3-phenylpropyrylamino)-(tert-butoxycarbonylmethylcarbamoyl)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

(2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-((S)-2-benzyloxycarbonylamino-3,3-dimethylbutyrylamino)-(tert-butoxycarbonylmethylcarbamoyl)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

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