(6S)-7-(tert-butyldimethylsilyloxy)-6-(tert-butoxycarbonylamino)-1-(p-toluenesulfonyl)-4-hepten-3-one

Base Information

Chemical Name:(6S)-7-(tert-butyldimethylsilyloxy)-6-(tert-butoxycarbonylamino)-1-(p-toluenesulfonyl)-4-hepten-3-one
CAS No.:629648-04-0
Molecular Formula:C₂₅H₄₁NO₆SSi
Molecular Weight:511.755
Hs Code.:

Synonyms:(6S)-7-(tert-butyldimethylsilyloxy)-6-(tert-butoxycarbonylamino)-1-(p-toluenesulfonyl)-4-hepten-3-one

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Chemical Property of (6S)-7-(tert-butyldimethylsilyloxy)-6-(tert-butoxycarbonylamino)-1-(p-toluenesulfonyl)-4-hepten-3-one

Chemical Property:

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Technology Process of (6S)-7-(tert-butyldimethylsilyloxy)-6-(tert-butoxycarbonylamino)-1-(p-toluenesulfonyl)-4-hepten-3-one

There total 1 articles about (6S)-7-(tert-butyldimethylsilyloxy)-6-(tert-butoxycarbonylamino)-1-(p-toluenesulfonyl)-4-hepten-3-one 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%

: 124085-68-3
tert-butyl (R)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate

: 205816-66-6
4-[(4'-methylphenyl)sulfonyl]-1-(triphenyphosphoranylidene)-2-butanone

: 629648-04-0
(6S)-7-(tert-butyldimethylsilyloxy)-6-(tert-butoxycarbonylamino)-1-(p-toluenesulfonyl)-4-hepten-3-one

Guidance literature:: In chloroform; at 25 ℃; for 30h;
DOI:10.1016/j.tet.2003.08.060

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 100-46-9
benzylamine

: 629648-04-0
(6S)-7-(tert-butyldimethylsilyloxy)-6-(tert-butoxycarbonylamino)-1-(p-toluenesulfonyl)-4-hepten-3-one

: 629648-08-4
(1S,2'R)-1-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-2-(tert-butyldimethylsilyloxy)ethylcarbamic acid tert-butyl ester

: 629648-13-1
(1S,2'S)-1-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-2-(tert-butyldimethylsilyloxy)ethylcarbamic acid tert-butyl ester

Guidance literature:: benzylamine; (6S)-7-(tert-butyldimethylsilyloxy)-6-(tert-butoxycarbonylamino)-1-(p-toluenesulfonyl)-4-hepten-3-one; In tetrahydrofuran; at 0 ℃; for 120h;

With palladium dihydroxide; hydrogen; In methanol; at 25 ℃; for 20h; under 2585.74 Torr;

benzyl chloroformate; With sodium carbonate; In tetrahydrofuran; water; at 20 ℃; for 12h;
DOI:10.1016/j.tet.2003.08.060

Reference yield:

: 629648-04-0
(6S)-7-(tert-butyldimethylsilyloxy)-6-(tert-butoxycarbonylamino)-1-(p-toluenesulfonyl)-4-hepten-3-one

: 400009-40-7
(2S,2'R)-tert-butoxycarbonylamino-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-acetic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 120 h / 0 °C

1.2: H₂; Pd(OH)2 / methanol / 20 h / 25 °C / 2585.74 Torr

1.3: 0.20 g / Na₂CO₃*10H₂O / tetrahydrofuran; H₂O / 12 h / 20 °C

2.1: 94 percent / Bu₄NF / tetrahydrofuran / 20 °C

3.1: 83 percent / Jones reagent / acetone / 5 h / 0 - 20 °C

With jones reagent; tetrabutyl ammonium fluoride; In tetrahydrofuran; acetone; 1.1: Michael reaction;
DOI:10.1016/j.tet.2003.08.060