(2S,3R,6S,E)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-methyl-6-(5-(phenylsulfonyl)pent-4-enyl)piperidine-1-carboxylate

Base Information

Chemical Name:(2S,3R,6S,E)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-methyl-6-(5-(phenylsulfonyl)pent-4-enyl)piperidine-1-carboxylate
CAS No.:906097-71-0
Molecular Formula:C₂₈H₄₇NO₅SSi
Molecular Weight:537.836
Hs Code.:

Synonyms:(2S,3R,6S,E)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-methyl-6-(5-(phenylsulfonyl)pent-4-enyl)piperidine-1-carboxylate

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Chemical Property of (2S,3R,6S,E)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-methyl-6-(5-(phenylsulfonyl)pent-4-enyl)piperidine-1-carboxylate

Chemical Property:

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Technology Process of (2S,3R,6S,E)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-methyl-6-(5-(phenylsulfonyl)pent-4-enyl)piperidine-1-carboxylate

There total 8 articles about (2S,3R,6S,E)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-methyl-6-(5-(phenylsulfonyl)pent-4-enyl)piperidine-1-carboxylate 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:

: 3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(4-oxo-butyl)-piperidine-1-carboxylic acid tert-butyl ester

: 56069-39-7
diethyl phenylsulfonylmethylphosphonate

: 906097-71-0
(2S,3R,6S,E)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-methyl-6-(5-(phenylsulfonyl)pent-4-enyl)piperidine-1-carboxylate

Guidance literature:: diethyl phenylsulfonylmethylphosphonate; With sodium hydride; In tetrahydrofuran; for 0.5h; cooling;

3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(4-oxo-butyl)-piperidine-1-carboxylic acid tert-butyl ester; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ol060960b

Reference yield:

: 906097-67-4
(2S,3R)-tert-butyl 3-(tert-butyldimethylsilyloxy)-6-(4-hydroxybutyl)-2-methyl-3,4-dihydropyridine-1(2H)-carboxylate

: 906097-71-0
(2S,3R,6S,E)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-methyl-6-(5-(phenylsulfonyl)pent-4-enyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 80 percent / sodium cyanoborohydride; trifluoroacetic acid / CH₂Cl₂ / 4 h / -42 °C

2.1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

3.1: sodium hydride / tetrahydrofuran / 0.5 h / cooling

3.2: 47 mg / tetrahydrofuran / 20 °C

With oxalyl dichloride; sodium hydride; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation / 3.2: Wittig reaction;
DOI:10.1021/ol060960b

Reference yield:

: 906097-68-5
(2S,3R,6S)-tert-butyl 3-(tert-butyldimethylsilyloxy)-6-(4-hydroxybutyl)-2-methylpiperidine-1-carboxylate

: 906097-71-0
(2S,3R,6S,E)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-methyl-6-(5-(phenylsulfonyl)pent-4-enyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

2.1: sodium hydride / tetrahydrofuran / 0.5 h / cooling

2.2: 47 mg / tetrahydrofuran / 20 °C

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation / 2.2: Wittig reaction;
DOI:10.1021/ol060960b