(2S,5R,6S)-6-Allyl-5-hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

Chemical Name:(2S,5R,6S)-6-Allyl-5-hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
CAS No.:865474-08-4
Molecular Formula:C₁₈H₂₃NO₅
Molecular Weight:333.384
Hs Code.:

Synonyms:(2S,5R,6S)-6-Allyl-5-hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,5R,6S)-6-Allyl-5-hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Technology Process of (2S,5R,6S)-6-Allyl-5-hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 1 articles about (2S,5R,6S)-6-Allyl-5-hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl 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: 95.0%

: 824943-45-5
(2S,5R)-5-hydroxy-6-methoxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 762-72-1
allyl-trimethyl-silane

: 865474-08-4
(2S,5R,6S)-6-Allyl-5-hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -30 - 20 ℃;
DOI:10.1021/ol0515715

Reference yield: 98.0%

: 865474-08-4
(2S,5R,6S)-6-Allyl-5-hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 107-30-2
chloromethyl methyl ether

: 1012322-43-8
1-benzyl 2-methyl (5R,6S)-6-allyl-5-(methoxymethoxy)piperidine-1,2-dicarboxylate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1055/s-2007-1000831

Reference yield:

: 865474-08-4
(2S,5R,6S)-6-Allyl-5-hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: C₂₂H₃₁NO₅

Guidance literature:: Multi-step reaction with 5 steps

1.1: N-ethyl-N,N-diisopropylamine / chloroform / 15 h / 0 - 20 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / Inert atmosphere

2.2: 1 h / -78 - 0 °C / Inert atmosphere

3.1: tetrahydrofuran / 1 h / Inert atmosphere

4.1: lithium triethylborohydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

5.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

With oxalyl dichloride; lithium triethylborohydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; chloroform; 3.1: |Michael Addition / 5.1: |Swern Oxidation;
DOI:10.3184/174751917X14967701766987