(4S,4aS,7S,8R,8aS)-4-((S)-4-Benzyloxy-3-methyl-butyryl)-8-hydroxy-7-isopropyl-4a-methyl-octahydro-naphthalen-2-one

Base Information

Chemical Name:(4S,4aS,7S,8R,8aS)-4-((S)-4-Benzyloxy-3-methyl-butyryl)-8-hydroxy-7-isopropyl-4a-methyl-octahydro-naphthalen-2-one
CAS No.:160715-33-3
Molecular Formula:C₂₆H₃₈O₄
Molecular Weight:414.585
Hs Code.:

Synonyms:(4S,4aS,7S,8R,8aS)-4-((S)-4-Benzyloxy-3-methyl-butyryl)-8-hydroxy-7-isopropyl-4a-methyl-octahydro-naphthalen-2-one

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Chemical Property of (4S,4aS,7S,8R,8aS)-4-((S)-4-Benzyloxy-3-methyl-butyryl)-8-hydroxy-7-isopropyl-4a-methyl-octahydro-naphthalen-2-one

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Technology Process of (4S,4aS,7S,8R,8aS)-4-((S)-4-Benzyloxy-3-methyl-butyryl)-8-hydroxy-7-isopropyl-4a-methyl-octahydro-naphthalen-2-one

There total 12 articles about (4S,4aS,7S,8R,8aS)-4-((S)-4-Benzyloxy-3-methyl-butyryl)-8-hydroxy-7-isopropyl-4a-methyl-octahydro-naphthalen-2-one 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: 99.0%

: 160797-64-8
(+)-(1R,3S,5S,6R,7R,8S,9S,12S,2'S)-6-(3'-Benzyloxy-2'-methylpropyl)-3-ethoxy-9-methyl-12-isopropyl-2-oxatetracyclo[6.4.0.0^3,7.0^5,9]dodecan-6-ol

: 160715-33-3
(4S,4aS,7S,8R,8aS)-4-((S)-4-Benzyloxy-3-methyl-butyryl)-8-hydroxy-7-isopropyl-4a-methyl-octahydro-naphthalen-2-one

Guidance literature:: With boron trifluoride diethyl etherate; In acetonitrile; at -18 ℃; for 48h;
DOI:10.1007/BF00812715

Reference yield:

: (+/-)-(1S*,3R*,5R*,7R*,8R*,9R*,12R*)-3-Ethoxy-12-isopropyl-9-methyl-2-oxatetracyclo[6.4.0.0^3,7.0^5,9]dodecan-6-on

: 160715-33-3
(4S,4aS,7S,8R,8aS)-4-((S)-4-Benzyloxy-3-methyl-butyryl)-8-hydroxy-7-isopropyl-4a-methyl-octahydro-naphthalen-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: toluene; diethyl ether / 1.) -60 deg C to r.t., 2.) r.t., 22 h

2: 99 percent / acid, LiClO₄ / diethyl ether / 6 h / Ambient temperature

With lithium perchlorate; In diethyl ether; toluene;
DOI:10.1002/(SICI)1521-3773(19980904)37:16<2226::AID-ANIE2226>3.0.CO;2-H

Reference yield:

: 490-91-5
thymoquinone

: 160715-33-3
(4S,4aS,7S,8R,8aS)-4-((S)-4-Benzyloxy-3-methyl-butyryl)-8-hydroxy-7-isopropyl-4a-methyl-octahydro-naphthalen-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: 76 percent / melt / 120 h / 118 °C

2: 45 percent / Zn, CH₃COOH, air / 1 h / 40 °C

3: NaBH₄ / methanol / 0.75 h / Ambient temperature

5: 76 percent / DMAP, pyridine / 16 h / 60 °C

6: 62 percent / Na, ethanol / 2 h / Heating

7: 94 percent / 2percent HCl / H₂O; tetrahydrofuran / 40 h / Ambient temperature

8: 1.) 1.7M t-BuLi / 1.) ether, pentane, -78 deg C, 10 min; r.t., 2 h, 2.) ether, pentane, toluene, -78 deg C, 15 min; r.t., 22 h

9: 99 percent / BF₃*Et₂O / acetonitrile / 48 h / -18 °C

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; air; ethanol; boron trifluoride diethyl etherate; tert.-butyl lithium; sodium; acetic acid; zinc; In tetrahydrofuran; methanol; water; acetonitrile;
DOI:10.1007/BF00812715