N-{(E)-(R)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-hydroxy-but-2-enyl}-4-methyl-benzenesulfonamide

Base Information

Chemical Name:N-{(E)-(R)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-hydroxy-but-2-enyl}-4-methyl-benzenesulfonamide
CAS No.:220307-03-9
Molecular Formula:C₁₉H₃₃NO₄SSi
Molecular Weight:399.627
Hs Code.:

Synonyms:N-{(E)-(R)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-hydroxy-but-2-enyl}-4-methyl-benzenesulfonamide

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Chemical Property of N-{(E)-(R)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-hydroxy-but-2-enyl}-4-methyl-benzenesulfonamide

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Technology Process of N-{(E)-(R)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-hydroxy-but-2-enyl}-4-methyl-benzenesulfonamide

There total 4 articles about N-{(E)-(R)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-hydroxy-but-2-enyl}-4-methyl-benzenesulfonamide 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: 90.0%

: 220307-00-6
(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(toluene-4-sulfonylamino)-hex-2-enoic acid methyl ester

: 220307-03-9
N-{(E)-(R)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-hydroxy-but-2-enyl}-4-methyl-benzenesulfonamide

Guidance literature:: With diisobutylaluminium hydride; In chloroform; toluene; at -78 ℃; for 1h;
DOI:10.1039/a806882h

Reference yield:

: N-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-propyl]-4-methyl-benzenesulfonamide

: 220307-03-9
N-{(E)-(R)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-hydroxy-but-2-enyl}-4-methyl-benzenesulfonamide

Guidance literature:: Multi-step reaction with 2 steps

1: CHCl₃ / 1 h / 0 - 20 °C

2: 90 percent / DIBAL / toluene; CHCl₃ / 1 h / -78 °C

With diisobutylaluminium hydride; In chloroform; toluene;
DOI:10.1039/a806882h

Reference yield:

: 220306-97-8
N-[(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxymethyl-propyl]-4-methyl-benzenesulfonamide

: 220307-03-9
N-{(E)-(R)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-hydroxy-but-2-enyl}-4-methyl-benzenesulfonamide

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) (COCl)2, DMSO, 2.) (i-Pr)2NEt / 1.) CHCl₃, hexane, -78 deg C, 30 min, 2.) -78 to 0 deg C, 30 min

2: CHCl₃ / 1 h / 0 - 20 °C

3: 90 percent / DIBAL / toluene; CHCl₃ / 1 h / -78 °C

With oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In chloroform; toluene;
DOI:10.1039/a806882h