1H-Indole-4,5,6-triol, octahydro-1-(2-hydroxyethyl)-, (3aS,4R,5R,6S,7aS)- (9CI)

Base Information

Chemical Name:1H-Indole-4,5,6-triol, octahydro-1-(2-hydroxyethyl)-, (3aS,4R,5R,6S,7aS)- (9CI)
CAS No.:637034-24-3
Molecular Formula:C10H19NO4
Molecular Weight:217.26216
Hs Code.:
Mol file:637034-24-3.mol

Synonyms:1H-Indole-4,5,6-triol, octahydro-1-(2-hydroxyethyl)-, (3aS,4R,5R,6S,7aS)- (9CI)

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 1H-Indole-4,5,6-triol, octahydro-1-(2-hydroxyethyl)-, (3aS,4R,5R,6S,7aS)- (9CI)

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Technology Process of 1H-Indole-4,5,6-triol, octahydro-1-(2-hydroxyethyl)-, (3aS,4R,5R,6S,7aS)- (9CI)

There total 6 articles about 1H-Indole-4,5,6-triol, octahydro-1-(2-hydroxyethyl)-, (3aS,4R,5R,6S,7aS)- (9CI) 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%

: 637034-20-9
[3aS,4R,5S,6S,7aS]-1-(2'-hydroxyethyl)-6-O-tert-butyl(dimethyl)silyl-4,5-O-(1-methylethylidene)-4,5,6-trihydroxyoctahydroindole

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

Guidance literature:: With trifluoroacetic acid;
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

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

Guidance literature:: Multi-step reaction with 6 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: 62 percent / sodium cyanoborohydride; acetic acid / methanol / 24 h / 20 °C

6.1: 98 percent / trifluoroacetic acid / H₂O / 14 h / 20 °C

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

Reference yield:

: 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

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

Guidance literature:: Multi-step reaction with 2 steps

1: 62 percent / sodium cyanoborohydride; acetic acid / methanol / 24 h / 20 °C

2: 98 percent / trifluoroacetic acid / H₂O / 14 h / 20 °C

With sodium cyanoborohydride; acetic acid; trifluoroacetic acid; In methanol; water;
DOI:10.1016/j.tet.2003.09.044