(2aS,3S,5aR,6R,8aR,8bR)-3,6-dimethyl-6-phenylsulfanylmethyl-2a-[2-(tetrahydropyran-2-yloxy)ethyl]decahydronaphtho[1,8-bc]furan-2-one

Base Information

Chemical Name:(2aS,3S,5aR,6R,8aR,8bR)-3,6-dimethyl-6-phenylsulfanylmethyl-2a-[2-(tetrahydropyran-2-yloxy)ethyl]decahydronaphtho[1,8-bc]furan-2-one
CAS No.:535932-73-1
Molecular Formula:C₂₇H₃₈O₄S
Molecular Weight:458.662
Hs Code.:

Synonyms:(2aS,3S,5aR,6R,8aR,8bR)-3,6-dimethyl-6-phenylsulfanylmethyl-2a-[2-(tetrahydropyran-2-yloxy)ethyl]decahydronaphtho[1,8-bc]furan-2-one

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Chemical Property of (2aS,3S,5aR,6R,8aR,8bR)-3,6-dimethyl-6-phenylsulfanylmethyl-2a-[2-(tetrahydropyran-2-yloxy)ethyl]decahydronaphtho[1,8-bc]furan-2-one

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Technology Process of (2aS,3S,5aR,6R,8aR,8bR)-3,6-dimethyl-6-phenylsulfanylmethyl-2a-[2-(tetrahydropyran-2-yloxy)ethyl]decahydronaphtho[1,8-bc]furan-2-one

There total 8 articles about (2aS,3S,5aR,6R,8aR,8bR)-3,6-dimethyl-6-phenylsulfanylmethyl-2a-[2-(tetrahydropyran-2-yloxy)ethyl]decahydronaphtho[1,8-bc]furan-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: 97.0%

: 96388-83-9
2-tetrahydropyranyloxy-1-iodoethane

: 535932-84-4
(2aS,3S,5aR,6R,8aR,8bR)-3,6-Dimethyl-6-phenylsulfanylmethyl-decahydro-naphtho[1,8-bc]furan-2-one

: 535932-73-1
(2aS,3S,5aR,6R,8aR,8bR)-3,6-dimethyl-6-phenylsulfanylmethyl-2a-[2-(tetrahydropyran-2-yloxy)ethyl]decahydronaphtho[1,8-bc]furan-2-one

Guidance literature:: (2aS,3S,5aR,6R,8aR,8bR)-3,6-Dimethyl-6-phenylsulfanylmethyl-decahydro-naphtho[1,8-bc]furan-2-one; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

2-tetrahydropyranyloxy-1-iodoethane; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; hexane; at 0 ℃; for 2h;
DOI:10.1021/jo020743y

Reference yield:

: 14204-24-1
N-(phenylthio)succinimide

: 535932-73-1
(2aS,3S,5aR,6R,8aR,8bR)-3,6-dimethyl-6-phenylsulfanylmethyl-2a-[2-(tetrahydropyran-2-yloxy)ethyl]decahydronaphtho[1,8-bc]furan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 79 percent / Bu₃P; pyridine / 1.5 h / 60 °C

2.1: BuLi; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / 0 °C

2.2: 97 percent / HMPA / hexane; tetrahydrofuran / 2 h / 0 °C

With pyridine; n-butyllithium; tributylphosphine; diisopropylamine; In tetrahydrofuran; hexane;
DOI:10.1021/jo020743y

Reference yield:

: 331627-49-7
(1S,4R)-3-(2-Benzenesulfinyl-ethyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-cyclohex-2-enol

: 535932-73-1
(2aS,3S,5aR,6R,8aR,8bR)-3,6-dimethyl-6-phenylsulfanylmethyl-2a-[2-(tetrahydropyran-2-yloxy)ethyl]decahydronaphtho[1,8-bc]furan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 91 percent / DEAD; PPh₃ / tetrahydrofuran / 1 h / 20 °C

2.1: 84 percent / ethyl propiolate; pyridine / toluene / 61 h / Heating

3.1: H₂; PtO₂ / acetic acid / 30 h / 20 °C / 3040 Torr

4.1: 369 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

5.1: 79 percent / Bu₃P; pyridine / 1.5 h / 60 °C

6.1: BuLi; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / 0 °C

6.2: 97 percent / HMPA / hexane; tetrahydrofuran / 2 h / 0 °C

With pyridine; platinum(IV) oxide; n-butyllithium; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; diisopropylamine; triphenylphosphine; propynoic acid ethyl ester; diethylazodicarboxylate; In tetrahydrofuran; hexane; acetic acid; toluene; 1.1: Mitsunobu reaction / 2.1: intramolecular Diels-Alder reaction;
DOI:10.1021/jo020743y