(1R.5R,8R)-8-benzyloxy-3-(ethylthio)-2,7,7-trimethylbicyclo<3.3.0>oct-2-ene

Base Information

Chemical Name:(1R.5R,8R)-8-benzyloxy-3-(ethylthio)-2,7,7-trimethylbicyclo<3.3.0>oct-2-ene
CAS No.:225790-31-8
Molecular Formula:C₂₀H₂₈OS
Molecular Weight:316.508
Hs Code.:

Synonyms:(1R.5R,8R)-8-benzyloxy-3-(ethylthio)-2,7,7-trimethylbicyclo<3.3.0>oct-2-ene

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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 (1R.5R,8R)-8-benzyloxy-3-(ethylthio)-2,7,7-trimethylbicyclo<3.3.0>oct-2-ene

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Technology Process of (1R.5R,8R)-8-benzyloxy-3-(ethylthio)-2,7,7-trimethylbicyclo<3.3.0>oct-2-ene

There total 8 articles about (1R.5R,8R)-8-benzyloxy-3-(ethylthio)-2,7,7-trimethylbicyclo<3.3.0>oct-2-ene 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: 96.0%

: 75-08-1
ethanethiol

: (1R,5R,8R)-8-benzyloxy-2,7,7-trimethylbicyclo<3.3.0>octan-3-one

: 225790-31-8
(1R.5R,8R)-8-benzyloxy-3-(ethylthio)-2,7,7-trimethylbicyclo<3.3.0>oct-2-ene

Guidance literature:: With chloro-trimethyl-silane; In dichloromethane; for 3h; Ambient temperature;
DOI:10.1021/jo981478c

Reference yield:

: 18240-74-9
2,2-dimethyl-4,4-diethoxybutyronitrile

: 225790-31-8
(1R.5R,8R)-8-benzyloxy-3-(ethylthio)-2,7,7-trimethylbicyclo<3.3.0>oct-2-ene

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) N,N,N',N'-tetramethylethylenenediamine, BuLi / 1.) hexane, 18 deg C, 4 h, 2.) THF, hexane, -45 deg C (1 h), 0 deg C ( 1 h)

2: 1.) aq. H₂SO₄, 2.) aq. NaOH / 1.) THF, room temp., 1 h

3: 89 percent / DIBAL / hexane / 1 h / -78 °C

4: 99 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

5: aq. KH₂PO₄, Na₂HPO₄ / 65 h / Ambient temperature; lipase Amano PS

6: 98 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature

8: 96 percent / Me₃SiCl / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; sodium hydroxide; disodium hydrogenphosphate; potassium dihydrogenphosphate; n-butyllithium; chloro-trimethyl-silane; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo981478c

Reference yield:

: 186960-95-2
5,5-dimethyl-2-(methylthio)-2-cyclopenten-1-ol

: 225790-31-8
(1R.5R,8R)-8-benzyloxy-3-(ethylthio)-2,7,7-trimethylbicyclo<3.3.0>oct-2-ene

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

2: aq. KH₂PO₄, Na₂HPO₄ / 65 h / Ambient temperature; lipase Amano PS

3: 98 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature

5: 96 percent / Me₃SiCl / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; disodium hydrogenphosphate; potassium dihydrogenphosphate; chloro-trimethyl-silane; sodium hydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo981478c