(R)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-ethyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: (R)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-ethyl]-carbamic acid tert-butyl ester
• CAS No.: 197006-05-6
• Molecular Formula: C₂₀H₂₇NO₆
• Molecular Weight: 377.437
• Mol file: 197006-05-6.mol

Synonyms:(R)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-ethyl]-carbamic acid tert-butyl ester

Chemical Property of (R)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-ethyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-ethyl]-carbamic acid tert-butyl ester

There total 6 articles about (R)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-ethyl]-carbamic 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: 87.0%

(S)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (109579-08-0) → (R)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-ethyl]-carbamic acid tert-butyl ester (197006-05-6)

Guidance literature:

With sodium tetrahydroborate; acetic acid; In dichloromethane; at 0 - 25 ℃; for 27h; Inert atmosphere;

Reference yield: 76.0%

cycl-isopropylidene malonate (2033-24-1) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (R)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-ethyl]-carbamic acid tert-butyl ester (197006-05-6)

Guidance literature:

cycl-isopropylidene malonate; N-tert-butoxycarbonyl-L-phenylalanine; With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at -5 - 4 ℃; for 2h; Inert atmosphere;

With sodium tetrahydroborate; acetic acid; In dichloromethane; at -5 ℃; for 17h; Cooling; Inert atmosphere;

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (R)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-ethyl]-carbamic acid tert-butyl ester (197006-05-6)

Guidance literature:

Multi-step reaction with 2 steps

1: DMAP; DCC / CH₂Cl₂ / -5 °C

2: 13.530 g / NaBH₄; AcOH / CH₂Cl₂ / 18 h / -5 °C

With dmap; sodium tetrahydroborate; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/jo050645n

upstream raw materials:

(S)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

L-phenylalanine

di-tert-butyl dicarbonate

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

(R)-2-benzyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

(5R)-5-benzylpyrrolidin-2-one

(4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpentanoic acid

methyl (2S,4R)-4-[(tert-butoxycarbonyl)amino]-2-methyl-5-phenylpentanoate