[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tosyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one 1,3-propanedithioketal

Base Information

Chemical Name:[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tosyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one 1,3-propanedithioketal
CAS No.:637033-93-3
Molecular Formula:C₂₆H₄₂O₆S₃Si
Molecular Weight:574.899
Hs Code.:

[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tosyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one 1,3-propanedithioketal

Synonyms:[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tosyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one 1,3-propanedithioketal

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Chemical Property of [3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tosyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one 1,3-propanedithioketal

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Technology Process of [3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tosyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one 1,3-propanedithioketal

There total 1 articles about [3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tosyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one 1,3-propanedithioketal 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: 98.0%

: 98-59-9
p-toluenesulfonyl chloride

: 243978-58-7
[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-hydroxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one 1,3-propanedithioketal

: 637033-93-3
[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tosyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one 1,3-propanedithioketal

Guidance literature:: With dmap; triethylamine; In dichloromethane;
DOI:10.1055/s-2003-37112

Reference yield:

: 637033-93-3
[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tosyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one 1,3-propanedithioketal

: 637034-04-9
[3aS,4R,5S,6S,7aS]-1-benzyl-6-O-tert-butyl(dimethyl)silyl-4,5-O-(1-methylethylidene)-4,5,6-trihydroxyoctahydroindole

Guidance literature:: Multi-step reaction with 4 steps

1.1: 92 percent / dimethylsulfoxide / 4 h / 80 °C

2.1: di-iso-butylaluminium hydride / toluene / 1 h / -78 °C

2.2: 77 percent / phosphate buffer / toluene; acetone; ethyl acetate / 0.33 h / 20 °C / pH 7.2

3.1: 75 percent / N-bromosuccinimide / acetone; H₂O / 0.5 h / -50 °C

4.1: 50 percent / sodium cyanoborohydride; acetic acid / methanol / 24 h / 20 °C

With N-Bromosuccinimide; diisobutylaluminum hydride; sodium cyanoborohydride; acetic acid; In methanol; water; dimethyl sulfoxide; acetone; toluene;
DOI:10.1016/j.tet.2003.09.044

Reference yield:

: 637033-93-3
[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tosyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one 1,3-propanedithioketal

: 637034-24-3
[3aS,4R,5R,6S,7aS]-1-(2'-hydroxyethyl)octahydroindole-4,5,6-triol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 92 percent / dimethylsulfoxide / 4 h / 80 °C

2.1: di-iso-butylaluminium hydride / toluene / 1 h / -78 °C

2.2: 77 percent / phosphate buffer / toluene; acetone; ethyl acetate / 0.33 h / 20 °C / pH 7.2

3.1: 75 percent / N-bromosuccinimide / acetone; H₂O / 0.5 h / -50 °C

4.1: 62 percent / sodium cyanoborohydride; acetic acid / methanol / 24 h / 20 °C

5.1: 98 percent / trifluoroacetic acid / H₂O / 14 h / 20 °C

With N-Bromosuccinimide; diisobutylaluminum hydride; sodium cyanoborohydride; acetic acid; trifluoroacetic acid; In methanol; water; dimethyl sulfoxide; acetone; toluene;
DOI:10.1016/j.tet.2003.09.044