(2R,3R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyryloxy]-3-methyl-pentanoic acid benzyl ester

Base Information

• Chemical Name: (2R,3R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyryloxy]-3-methyl-pentanoic acid benzyl ester
• CAS No.: 182205-76-1
• Molecular Formula: C₂₉H₄₉NO₇Si
• Molecular Weight: 551.796
• Mol file: 182205-76-1.mol

Synonyms:(2R,3R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyryloxy]-3-methyl-pentanoic acid benzyl ester

Chemical Property of (2R,3R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyryloxy]-3-methyl-pentanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyryloxy]-3-methyl-pentanoic acid benzyl ester

There total 1 articles about (2R,3R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyryloxy]-3-methyl-pentanoic 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:

N-(tert-butoxycarbonyl)-3-hydroxy-L-valine (102507-13-1,105504-72-1) → (2R,3R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyryloxy]-3-methyl-pentanoic acid benzyl ester (182205-76-1)

Guidance literature:

Multi-step reaction with 2 steps

2: 40 percent / dicyclohexylcarbodiimide (DCC), DMAP

With dmap; dicyclohexyl-carbodiimide;

DOI:10.1016/0040-4039(96)01199-9

Reference yield: 50.0%

(2R,3R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyryloxy]-3-methyl-pentanoic acid benzyl ester (182205-76-1) + methyl iodide (74-88-4) → (2R,3R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyryloxy]-3-methyl-pentanoic acid benzyl ester (182205-77-2)

Guidance literature:

With silver(l) oxide; In N,N-dimethyl-formamide; for 18h; Ambient temperature;

DOI:10.1016/0040-4039(96)01199-9

Reference yield:

(2R,3R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyryloxy]-3-methyl-pentanoic acid benzyl ester (182205-76-1) → aureobasidin A (127785-64-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 50 percent / Ag₂O / dimethylformamide / 18 h / Ambient temperature

2: H₂ / Pd/C

3: N-methylmorpholine (NMM), bis(2-oxo-3-oxazolidinyl)phosphinic chloride (Bop-Cl)

4: 50percent TFA / CH₂Cl₂

7: H₂ / 10percent Pd/C

8: 1.) 50percent TFA; 2.) 1N HCl / 1.) CH₂Cl₂

9: benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP), DMAP / CH₂Cl₂

With 4-methyl-morpholine; hydrogenchloride; dmap; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; trifluoroacetic acid; silver(l) oxide; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(96)01199-9

upstream raw materials:

N-(tert-butoxycarbonyl)-3-hydroxy-L-valine

Downstream raw materials:

(2R,3R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyryloxy]-3-methyl-pentanoic acid benzyl ester

aureobasidin A

C₇₂H₁₀₈N₈O₁₄

(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyric acid (1R,2R)-1-[((S)-1-benzyloxycarbonyl-2-methyl-propyl)-methyl-carbamoyl]-2-methyl-butyl ester