(R)-4-(BOC-AMINO)-5-TBDPS-PENTANOIC ACID

Base Information

• Chemical Name: (R)-4-(BOC-AMINO)-5-TBDPS-PENTANOIC ACID
• CAS No.: 138629-31-9
• Molecular Formula: C16H33NO4Si
• Molecular Weight: 471.669
• Mol file: 138629-31-9.mol

Synonyms:(R)-4-(BOC-AMINO)-5-TBDPS-PENTANOIC ACID;(R)-4-(TERT-BUTOXYCARBONYLAMINO)-5-(TERT-BUTYLDIPHENYLSILYLOXY) PENTANOIC ACID

Chemical Property of (R)-4-(BOC-AMINO)-5-TBDPS-PENTANOIC ACID

Chemical Property:

• PSA: 84.86000
• LogP: 4.71200

Purity/Quality:

(R)-4-(TERT-BUTOXYCARBONYLAMINO)-5-(TERT-BUTYLDIPHENYLSILYLOXY) PENTANOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-4-(BOC-AMINO)-5-TBDPS-PENTANOIC ACID

There total 6 articles about (R)-4-(BOC-AMINO)-5-TBDPS-PENTANOIC ACID 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:

ethyl (R)-2-pyrrolidone-5-carboxylate (68766-96-1) → (R)-4-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid (138629-31-9)

Guidance literature:

Multi-step reaction with 4 steps

1: LiBH₄

2: Et₃N, 4-dimethylaminopyridine

3: Et₃N, 4-dimethylaminopyridine

4: LiOOH, H₂O

With dmap; lithium borohydride; lithium hydroperoxide; water; triethylamine;

DOI:10.1021/ja00030a063

Reference yield:

(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester (138629-30-8) → (R)-4-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid (138629-31-9)

Guidance literature:

With lithium hydroperoxide; water;

DOI:10.1021/ja00030a063

Reference yield:

D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (R)-4-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid (138629-31-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / SOCl₂, KOH / 150 °C

2: LiBH₄

3: Et₃N, 4-dimethylaminopyridine

4: Et₃N, 4-dimethylaminopyridine

5: LiOOH, H₂O

With dmap; potassium hydroxide; lithium borohydride; thionyl chloride; lithium hydroperoxide; water; triethylamine;

DOI:10.1021/ja00030a063

upstream raw materials:

(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester

D-Glutamic acid

(R)-5-hydroxymethylpyrrolidin-2-one

(R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-2-one

Downstream raw materials:

[(R)-4-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-1-(tert-butyl-diphenyl-silanyloxymethyl)-4-oxo-butyl]-carbamic acid tert-butyl ester

(S)-4-[(R)-4-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-1-(tert-butyl-diphenyl-silanyloxymethyl)-4-oxo-butylcarbamoyl]-2-tert-butoxycarbonylamino-butyric acid benzyl ester

(S)-4-{1-Benzyl-4-[3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propyl]-1H-imidazol-2-yl}-2-tert-butoxycarbonylamino-butyric acid benzyl ester

(S)-4-[4-((S)-2-Acetylamino-2-methoxycarbonyl-ethyl)-1-benzyl-1H-imidazol-2-yl]-2-tert-butoxycarbonylamino-butyric acid benzyl ester

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