(2S,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(toluene-4-sulfonyl)-pentane-1,2-diol

Base Information

Chemical Name:(2S,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(toluene-4-sulfonyl)-pentane-1,2-diol
CAS No.:333335-30-1
Molecular Formula:C₂₈H₃₆O₅SSi
Molecular Weight:512.742
Hs Code.:

Synonyms:(2S,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(toluene-4-sulfonyl)-pentane-1,2-diol

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Chemical Property of (2S,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(toluene-4-sulfonyl)-pentane-1,2-diol

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Technology Process of (2S,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(toluene-4-sulfonyl)-pentane-1,2-diol

There total 8 articles about (2S,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(toluene-4-sulfonyl)-pentane-1,2-diol 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: 78.0%

: 333335-39-0
tert-Butyl-[(S)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(toluene-4-sulfonyl)-propoxy]-diphenyl-silane

: 333335-30-1
(2S,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(toluene-4-sulfonyl)-pentane-1,2-diol

Guidance literature:: With camphor-10-sulfonic acid; In methanol; at 0 ℃;
DOI:10.1055/s-2001-9717

Reference yield:

: 63305-65-7
3-((4-methylphenyl)sulfonyl)propanal

: 333335-30-1
(2S,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(toluene-4-sulfonyl)-pentane-1,2-diol

Guidance literature:: Multi-step reaction with 8 steps

1: 74 percent / NaH / tetrahydrofuran / 0 °C

2: 90 percent / DIBALH / diethyl ether / -70 °C

3: 84 percent / Ti(Oi-Pr)4; (-)-DIPT; t-BuOOH / 3 Angstroem molecular sieves / CH₂Cl₂

4: 73 percent / Ti(Oi-Pr)4 / CH₂Cl₂

5: p-TsOH / dimethylsulfoxide

6: DIBALH / diethyl ether / -70 °C

7: 92 percent / imidazole / CH₂Cl₂

8: 78 percent / CSA / methanol / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; 3 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; 1: Wittig-Horner reaction / 3: Sharpless asymmetric epoxidation;
DOI:10.1055/s-2001-9717

Reference yield:

: 333335-37-8
(E)-5-(Toluene-4-sulfonyl)-pent-2-en-1-ol

: 333335-30-1
(2S,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(toluene-4-sulfonyl)-pentane-1,2-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / Ti(Oi-Pr)4; (-)-DIPT; t-BuOOH / 3 Angstroem molecular sieves / CH₂Cl₂

2: 73 percent / Ti(Oi-Pr)4 / CH₂Cl₂

3: p-TsOH / dimethylsulfoxide

4: DIBALH / diethyl ether / -70 °C

5: 92 percent / imidazole / CH₂Cl₂

6: 78 percent / CSA / methanol / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; camphor-10-sulfonic acid; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; 3 A molecular sieve; In methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; 1: Sharpless asymmetric epoxidation;
DOI:10.1055/s-2001-9717