(-)-(4aS,6R,8aS)-3.4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-5,5,8a-trimethyl-1(2H)-naphthalenone 1-ethylene ketal

Base Information

Chemical Name:(-)-(4aS,6R,8aS)-3.4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-5,5,8a-trimethyl-1(2H)-naphthalenone 1-ethylene ketal
CAS No.:155393-00-3
Molecular Formula:C₂₂H₃₂O₃
Molecular Weight:344.494
Hs Code.:

Synonyms:(-)-(4aS,6R,8aS)-3.4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-5,5,8a-trimethyl-1(2H)-naphthalenone 1-ethylene ketal

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Chemical Property of (-)-(4aS,6R,8aS)-3.4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-5,5,8a-trimethyl-1(2H)-naphthalenone 1-ethylene ketal

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Technology Process of (-)-(4aS,6R,8aS)-3.4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-5,5,8a-trimethyl-1(2H)-naphthalenone 1-ethylene ketal

There total 2 articles about (-)-(4aS,6R,8aS)-3.4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-5,5,8a-trimethyl-1(2H)-naphthalenone 1-ethylene ketal 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: 92.0%

: 100-39-0
benzyl bromide

: 155486-87-6
(+)-(4aR,6S,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-hydroxy-5,5,8a-trimethyl-1(2H)-naphthalenone 1-ethylene ketal

: 155393-00-3
(-)-(4aS,6R,8aS)-3.4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-5,5,8a-trimethyl-1(2H)-naphthalenone 1-ethylene ketal

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 25 ℃; for 5h;
DOI:10.1248/cpb.41.1698

Reference yield:

: (+)-(4aR,8aR)-3,4,4a,5,8,8a-hexahydro-5,5,8a-trimethyl-1,6(2H,7H)-naphthalenedione 1-ethylene ketal

: 155393-00-3
(-)-(4aS,6R,8aS)-3.4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-5,5,8a-trimethyl-1(2H)-naphthalenone 1-ethylene ketal

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / 1 M K-Selectride / tetrahydrofuran / a) -78 deg C, 4 h, b) 25 deg C, 2.5 h

2: 92 percent / NaH / dimethylformamide / 5 h / 25 °C

With sodium hydride; potassium tri-sec-butyl-borohydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1248/cpb.41.1698