(2S,4S)-1-hydroxy-4-triisopropylsilanyloxy-5-benzyloxycarbonylaminopent-2-ylaminocarboxylic acid tert-butyl ester

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Chemical Name:(2S,4S)-1-hydroxy-4-triisopropylsilanyloxy-5-benzyloxycarbonylaminopent-2-ylaminocarboxylic acid tert-butyl ester
CAS No.:850996-95-1
Molecular Formula:C₂₇H₄₈N₂O₆Si
Molecular Weight:524.773
Hs Code.:

Synonyms:(2S,4S)-1-hydroxy-4-triisopropylsilanyloxy-5-benzyloxycarbonylaminopent-2-ylaminocarboxylic acid tert-butyl ester

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Chemical Property of (2S,4S)-1-hydroxy-4-triisopropylsilanyloxy-5-benzyloxycarbonylaminopent-2-ylaminocarboxylic acid tert-butyl ester

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Technology Process of (2S,4S)-1-hydroxy-4-triisopropylsilanyloxy-5-benzyloxycarbonylaminopent-2-ylaminocarboxylic acid tert-butyl ester

There total 9 articles about (2S,4S)-1-hydroxy-4-triisopropylsilanyloxy-5-benzyloxycarbonylaminopent-2-ylaminocarboxylic acid tert-butyl 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: 76.0%

: 850996-94-0
(4S)-[(2S)-3-benzyloxycarbonylamino-2-triisopropylsilanyloxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 850996-95-1
(2S,4S)-1-hydroxy-4-triisopropylsilanyloxy-5-benzyloxycarbonylaminopent-2-ylaminocarboxylic acid tert-butyl ester

Guidance literature:: With pyridinium p-toluenesulfonate; In methanol; at 60 ℃; for 4.5h;
DOI:10.1021/ol0503182

Reference yield:

: 850996-87-1
(4S)-4-[2-(1-methoxy-1-methylethoxy)ethyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 850996-95-1
(2S,4S)-1-hydroxy-4-triisopropylsilanyloxy-5-benzyloxycarbonylaminopent-2-ylaminocarboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 14.64 g / silica gel / CH₂Cl₂; H₂O / 72 h / 20 °C

2.1: 97 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -60 - 20 °C

3.1: Cu(OAc)2*H₂O; 2,2-bis[(3aS,8aR)-3a,8,8a-3H-indeno[3,2-d]oxazol-2yl]propane / ethanol / 120 h / 20 °C

3.2: 2,6-lutidine / CH₂Cl₂ / 16.5 h / 0 - 20 °C

3.3: HCO₂NH₄ / Pd/C / methanol / 24 h / 20 °C

4.1: 1.445 g / Et₃N / CH₂Cl₂ / 70 h / 20 °C

5.1: 76 percent / pyridinium p-toluene sulfonate / methanol / 4.5 h / 60 °C

With copper diacetate; oxalyl dichloride; 2,2-bis[(3aS,8aR)-3a,8,8a-3H-indeno[3,2-d]oxazol-2yl]propane; pyridinium p-toluenesulfonate; silica gel; dimethyl sulfoxide; triethylamine; In methanol; ethanol; dichloromethane; water; 2.1: Swern oxidation / 3.1: Henry reaction;
DOI:10.1021/ol0503182

Reference yield:

: 4-(3-amino-2-triisopropylsilanyloxy-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 850996-95-1
(2S,4S)-1-hydroxy-4-triisopropylsilanyloxy-5-benzyloxycarbonylaminopent-2-ylaminocarboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.445 g / Et₃N / CH₂Cl₂ / 70 h / 20 °C

2: 76 percent / pyridinium p-toluene sulfonate / methanol / 4.5 h / 60 °C

With pyridinium p-toluenesulfonate; triethylamine; In methanol; dichloromethane;
DOI:10.1021/ol0503182