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

Base Information

Chemical Name:[3aS,4R,5S,6S,7aS]-1-benzyl-6-O-tert-butyl(dimethyl)silyl-4,5-O-(1-methylethylidene)-4,5,6-trihydroxyoctahydroindole
CAS No.:637034-04-9
Molecular Formula:C₂₄H₃₉NO₃Si
Molecular Weight:417.664
Hs Code.:

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

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Chemical Property of [3aS,4R,5S,6S,7aS]-1-benzyl-6-O-tert-butyl(dimethyl)silyl-4,5-O-(1-methylethylidene)-4,5,6-trihydroxyoctahydroindole

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Technology Process of [3aS,4R,5S,6S,7aS]-1-benzyl-6-O-tert-butyl(dimethyl)silyl-4,5-O-(1-methylethylidene)-4,5,6-trihydroxyoctahydroindole

There total 5 articles about [3aS,4R,5S,6S,7aS]-1-benzyl-6-O-tert-butyl(dimethyl)silyl-4,5-O-(1-methylethylidene)-4,5,6-trihydroxyoctahydroindole 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: 50.0%

: 100-46-9
benzylamine

: 637033-96-6
[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-formylmethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one

: 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:: With sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 24h;
DOI:10.1055/s-2003-37112

Reference yield:

: 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

: 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 5 steps

1.1: 98 percent / 4-(N,N-dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 14 h / 20 °C

2.1: 92 percent / dimethylsulfoxide / 4 h / 80 °C

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

3.2: 77 percent / phosphate buffer / toluene; acetone; ethyl acetate / 0.33 h / 20 °C / pH 7.2

4.1: 75 percent / N-bromosuccinimide / acetone; H₂O / 0.5 h / -50 °C

5.1: 50 percent / sodium cyanoborohydride; acetic acid / methanol / 24 h / 20 °C

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

Reference yield:

: 637033-95-5
[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-formylmethyl-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 2 steps

1: 75 percent / N-bromosuccinimide / acetone; H₂O / 0.5 h / -50 °C

2: 50 percent / sodium cyanoborohydride; acetic acid / methanol / 24 h / 20 °C

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