N-[(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-formyl-butyl]-4-methyl-benzenesulfonamide

Base Information

Chemical Name:N-[(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-formyl-butyl]-4-methyl-benzenesulfonamide
CAS No.:132974-89-1
Molecular Formula:C₂₉H₃₇NO₄SSi
Molecular Weight:523.769
Hs Code.:

Synonyms:N-[(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-formyl-butyl]-4-methyl-benzenesulfonamide

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Chemical Property of N-[(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-formyl-butyl]-4-methyl-benzenesulfonamide

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Technology Process of N-[(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-formyl-butyl]-4-methyl-benzenesulfonamide

There total 11 articles about N-[(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-formyl-butyl]-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: 100.0%

: 132992-81-5
C₃₀H₃₇NO₅SSi

: 132974-89-1
N-[(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-formyl-butyl]-4-methyl-benzenesulfonamide

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃;
DOI:10.1016/0040-4039(91)80876-8

Reference yield:

: 132974-83-5
(5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one

: 132974-89-1
N-[(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-formyl-butyl]-4-methyl-benzenesulfonamide

Guidance literature:: Multi-step reaction with 8 steps

1: 1) LiHMDS / 1) THF, -20 deg C, 10 min

2: 1) LiHMDS / 1) THF, -20 deg C, 20 min

3: H₂O₂ / tetrahydrofuran; H₂O

4: 75 percent / diethyl ether / -78 °C

5: 1) NaHMDS 2) trans-2-(phenylsulfonyl)-3-phenyloxaziridine / 1) THF, -78 deg C, 15 min

6: 90 percent / DIBAL / CH₂Cl₂ / -78 deg C to r.t.; or LiAlH₄, THF, 0 deg C to reflux

7: 55 percent / Pb(OAc)4 / benzene / 0.5 h

8: 100 percent / LiOH / tetrahydrofuran; H₂O / 0 °C

With lead(IV) acetate; lithium hydroxide; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; N-(benzenesulfonyl)-3-phenyloxaziridine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water; benzene;
DOI:10.1016/0040-4039(91)80876-8

Reference yield:

: 132974-85-7
(-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosyl-1,5-dihydro-2H-pyrrol-2-one

: 132974-89-1
N-[(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-formyl-butyl]-4-methyl-benzenesulfonamide

Guidance literature:: Multi-step reaction with 5 steps

1: 75 percent / diethyl ether / -78 °C

2: 1) NaHMDS 2) trans-2-(phenylsulfonyl)-3-phenyloxaziridine / 1) THF, -78 deg C, 15 min

3: 90 percent / DIBAL / CH₂Cl₂ / -78 deg C to r.t.; or LiAlH₄, THF, 0 deg C to reflux

4: 55 percent / Pb(OAc)4 / benzene / 0.5 h

5: 100 percent / LiOH / tetrahydrofuran; H₂O / 0 °C

With lead(IV) acetate; lithium hydroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; N-(benzenesulfonyl)-3-phenyloxaziridine; In tetrahydrofuran; diethyl ether; dichloromethane; water; benzene;
DOI:10.1016/0040-4039(91)80876-8