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

Base Information

• Chemical Name: (2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-(tert-butoxycarbonylmethylcarbamoyl)-(2-nitrobenzenesulfonylamino)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester
• CAS No.: 870137-15-8
• Molecular Formula: C₄₇H₅₄N₄O₁₄S
• Molecular Weight: 931.03

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 10 articles about (2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-(tert-butoxycarbonylmethylcarbamoyl)-(2-nitrobenzenesulfonylamino)methyl]-1-methylprop-2-ynyloxy}phenyl)-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:

(4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-3-hydroxy-2-methylaminopropionic acid methyl ester (821006-11-5) → (2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-(tert-butoxycarbonylmethylcarbamoyl)-(2-nitrobenzenesulfonylamino)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester (870137-15-8)

Guidance literature:

Multi-step reaction with 4 steps

1: aq.LiOH

2: DBU

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

With lithium hydroxide; copper (I) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene;

DOI:10.1021/ol052287g

Reference yield:

(4S,5R)-5-(3-acetoxy-4-benzyloxyphenyl)-2-(4-methoxyphenyl)-3-methyloxazolidine-4-carboxylic acid methyl ester (821006-10-4) → (2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-(tert-butoxycarbonylmethylcarbamoyl)-(2-nitrobenzenesulfonylamino)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester (870137-15-8)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. HCl

2: aq.LiOH

3: DBU

4: 90 percent / CuOAc; DBU / toluene / 2 h / 0 °C

With hydrogenchloride; lithium hydroxide; copper (I) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene;

DOI:10.1021/ol052287g

Reference yield:

(2R,3R)-2-Amino-3-methyl-pent-4-yne-1,3-diol → (2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-(tert-butoxycarbonylmethylcarbamoyl)-(2-nitrobenzenesulfonylamino)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester (870137-15-8)

Guidance literature:

Multi-step reaction with 5 steps

1: Na₂CO₃

2: TEMPO

3: EDCI; HOBT

4: 84 percent / DEAD; PPh₃ / CH₂Cl₂

5: 90 percent / CuOAc; DBU / toluene / 2 h / 0 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; copper (I) acetate; sodium carbonate; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; diethylazodicarboxylate; In dichloromethane; toluene; 4: Mitsunobu reaction;

DOI:10.1021/ol052287g

upstream raw materials:

(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

(R)-4-((R)-1-hydroxy-1-methylprop-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(1R,2R)-N-(2-hydroxy-1-hydroxymethyl-2-methyl-but-3-ynyl)-2-nitrobenzenesulfonamide

Downstream raw materials:

(2S,3R)-3-(4-Benzyloxy-3-{(R)-1-[(S)-((S)-2-benzyloxycarbonylamino-propionylamino)-(tert-butoxycarbonylmethyl-carbamoyl)-methyl]-1-methyl-prop-2-ynyloxy}-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-propionic acid benzyl ester

(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

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