(S,S)-2-(3-benzyloxycarbonyl-2-tert-butoxycarbonylaminopropionylamino)-3-hydroxybutyric acid methylester

Base Information

• Chemical Name: (S,S)-2-(3-benzyloxycarbonyl-2-tert-butoxycarbonylaminopropionylamino)-3-hydroxybutyric acid methylester
• CAS No.: 946851-36-1
• Molecular Formula: C₂₁H₃₀N₂O₈
• Molecular Weight: 438.478
• Mol file: 946851-36-1.mol

Synonyms:(S,S)-2-(3-benzyloxycarbonyl-2-tert-butoxycarbonylaminopropionylamino)-3-hydroxybutyric acid methylester

Chemical Property of (S,S)-2-(3-benzyloxycarbonyl-2-tert-butoxycarbonylaminopropionylamino)-3-hydroxybutyric acid methylester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,S)-2-(3-benzyloxycarbonyl-2-tert-butoxycarbonylaminopropionylamino)-3-hydroxybutyric acid methylester

There total 2 articles about (S,S)-2-(3-benzyloxycarbonyl-2-tert-butoxycarbonylaminopropionylamino)-3-hydroxybutyric acid methylester 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: 86.0%

L-threonine methyl ester (3373-59-9) + BOC-L-aspartic acid 4-benzyl ester (7536-58-5,98482-77-0) → (S,S)-2-(3-benzyloxycarbonyl-2-tert-butoxycarbonylaminopropionylamino)-3-hydroxybutyric acid methylester (946851-36-1)

Guidance literature:

With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at -25 - 25 ℃; for 16h;

DOI:10.1002/anie.200700684

Reference yield: 84.0%

BOC-L-aspartic acid 4-benzyl ester (7536-58-5,98482-77-0) + L-threonine methyl ester hydrochloride (39994-75-7) → (S,S)-2-(3-benzyloxycarbonyl-2-tert-butoxycarbonylaminopropionylamino)-3-hydroxybutyric acid methylester (946851-36-1)

Guidance literature:

With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at -25 - 20 ℃; for 18h;

DOI:10.1002/chem.200701823

Reference yield:

(S,S)-2-(3-benzyloxycarbonyl-2-tert-butoxycarbonylaminopropionylamino)-3-hydroxybutyric acid methylester (946851-36-1) → C54H58N12O9S6Si

Guidance literature:

Multi-step reaction with 13 steps

1.1: 2-iodoxy benzoic acid / acetonitrile / 3.5 h / Heating

2.1: Lawesson reagent / tetrahydrofuran / 5 h / Heating

3.1: H₂ / Pd(OH)2/C / methanol / 16 h / 60 °C / 760.05 Torr

4.1: isobutyl chloroformate; N-methylmorpholine / tetrahydrofuran; H₂O / 1 h / -25 - 25 °C

5.1: LiOH / methanol / 16 h / 0 - 25 °C

6.1: N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 16 h / -10 - 25 °C

7.1: ethanol / 0 - 25 °C

8.1: N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 16 h / -10 - 25 °C

9.1: 87 percent / tri(2-furyl)phosphate / Pd₂(dibenzylideneacetone)3 / tetrahydrofuran; N,N-dimethyl-acetamide / 16 h / 45 °C

10.1: 48 percent / PdCl₂(PPh₃)2 / N,N-dimethyl-acetamide / 3.5 h / 45 °C

11.1: aq. LiOH / 2-methyl-propan-2-ol; tetrahydrofuran / 1 h / 25 °C

12.1: diphenylphosphoryl azide; iPr₂NEt / dimethylformamide / 16 h / 25 °C

12.2: Pd(PPh₃)4 / toluene / 85 °C

13.1: trifluoroacetic acid / CH₂Cl₂ / 2 h / 25 °C

With Lawessons reagent; 4-methyl-morpholine; lithium hydroxide; 2-iodoxybenzoic acid; diphenylphosphoranyl azide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; isobutyl chloroformate; bis-triphenylphosphine-palladium(II) chloride; palladium dihydroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 9.1: Negishi cross-coupling reaction / 10.1: Negishi cross-coupling reaction / 12.1: Stille coupling reaction;

DOI:10.1002/anie.200700684

upstream raw materials:

L-threonine methyl ester

BOC-L-aspartic acid 4-benzyl ester

L-threonine methyl ester hydrochloride

Downstream raw materials:

C₅₈H₆₆N₁₂O₉S₆Si

C₆₂H₇₁N₁₅O₁₁S₆Si

(S)-2-(2-benzyloxycarbonyl-1-tert-butoxycarbonylaminoethyl)-5-methylthiazole-4-carboxylic acid methyl ester