(S)-Piperidine-1,2-dicarboxylic acid 2-((R)-1-benzyloxycarbonyl-ethyl) ester 1-tert-butyl ester

Base Information

• Chemical Name: (S)-Piperidine-1,2-dicarboxylic acid 2-((R)-1-benzyloxycarbonyl-ethyl) ester 1-tert-butyl ester
• CAS No.: 187851-81-6
• Molecular Formula: C₂₁H₂₉NO₆
• Molecular Weight: 391.464

Synonyms:(S)-Piperidine-1,2-dicarboxylic acid 2-((R)-1-benzyloxycarbonyl-ethyl) ester 1-tert-butyl ester

Chemical Property of (S)-Piperidine-1,2-dicarboxylic acid 2-((R)-1-benzyloxycarbonyl-ethyl) ester 1-tert-butyl ester

Chemical Property:

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Technology Process of (S)-Piperidine-1,2-dicarboxylic acid 2-((R)-1-benzyloxycarbonyl-ethyl) ester 1-tert-butyl ester

There total 4 articles about (S)-Piperidine-1,2-dicarboxylic acid 2-((R)-1-benzyloxycarbonyl-ethyl) ester 1-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: 80.0%

benzyl (S)-Lactate (56777-24-3) + (S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid (26250-84-0) → (S)-Piperidine-1,2-dicarboxylic acid 2-((R)-1-benzyloxycarbonyl-ethyl) ester 1-tert-butyl ester (187851-81-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In diethyl ether; at 20 ℃; for 1h;

DOI:10.1016/S0960-894X(01)00748-X

Reference yield: 80.0%

(S)-2-(benzyloxy)propanoic acid (33106-32-0) + (S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid (26250-84-0) → (S)-Piperidine-1,2-dicarboxylic acid 2-((R)-1-benzyloxycarbonyl-ethyl) ester 1-tert-butyl ester (187851-81-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In diethyl ether; for 1h; Ambient temperature;

DOI:10.1016/S0040-4039(96)02454-9

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (S)-Piperidine-1,2-dicarboxylic acid 2-((R)-1-benzyloxycarbonyl-ethyl) ester 1-tert-butyl ester (187851-81-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / Et₃N / tetrahydrofuran / 2 h / Heating

2: 24 percent / DEAD; Ph₃P / diethyl ether / 1 h / 20 °C

With triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; 2: Mitsunobu reaction;

DOI:10.1021/jm020482k

upstream raw materials:

(S)-2-(benzyloxy)propanoic acid

(S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid

benzyl (S)-Lactate

di-tert-butyl dicarbonate

Downstream raw materials:

benzyl L-pipecolyl-D-lactate

N-methyl-L-leucyl-3-phenyl-D-lactyl-N-methyl-L-leucyl-D-lactyl-N-methyl-L-leucyl-3-phenyl-D-lactyl-L-pipecolyl-D-lactic acid

1-[2-(4-methyl-2-{methyl-[2-(4-methyl-2-{methyl-[2-(4-methyl-2-methylamino-pentanoyloxy)-3-phenyl-propionyl]-amino}-pentanoyloxy)-propionyl]-amino}-pentanoyloxy)-3-phenyl-propionyl]-piperidine-2-carboxylic acid 1-benzyloxycarbonyl-ethyl ester

C₆₃H₈₈N₄O₁₅

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