(1S,2S,3R,4S)-2-((Z)-2-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-vinyl)-3-methoxymethoxy-7,7-dimethyl-1-((Z)-2-phenylsulfanyl-vinyl)-bicyclo[2.2.1]heptan-2-ol

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Chemical Name:(1S,2S,3R,4S)-2-((Z)-2-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-vinyl)-3-methoxymethoxy-7,7-dimethyl-1-((Z)-2-phenylsulfanyl-vinyl)-bicyclo[2.2.1]heptan-2-ol
CAS No.:200859-97-8
Molecular Formula:C₃₇H₄₈O₇S
Molecular Weight:636.85
Hs Code.:

(1S,2S,3R,4S)-2-((Z)-2-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-vinyl)-3-methoxymethoxy-7,7-dimethyl-1-((Z)-2-phenylsulfanyl-vinyl)-bicyclo[2.2.1]heptan-2-ol

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Chemical Property of (1S,2S,3R,4S)-2-((Z)-2-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-vinyl)-3-methoxymethoxy-7,7-dimethyl-1-((Z)-2-phenylsulfanyl-vinyl)-bicyclo[2.2.1]heptan-2-ol

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Technology Process of (1S,2S,3R,4S)-2-((Z)-2-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-vinyl)-3-methoxymethoxy-7,7-dimethyl-1-((Z)-2-phenylsulfanyl-vinyl)-bicyclo[2.2.1]heptan-2-ol

There total 2 articles about (1S,2S,3R,4S)-2-((Z)-2-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-vinyl)-3-methoxymethoxy-7,7-dimethyl-1-((Z)-2-phenylsulfanyl-vinyl)-bicyclo[2.2.1]heptan-2-ol 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:

: 13884-92-9
phenylthiomethyl triphenylphosphonium chloride

: 200859-97-8
(1S,2S,3R,4S)-2-((Z)-2-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-vinyl)-3-methoxymethoxy-7,7-dimethyl-1-((Z)-2-phenylsulfanyl-vinyl)-bicyclo[2.2.1]heptan-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) potassium hexamethyldisilazide / 1.) toluene, THF, 0 deg C, 30 min, 2.) THF, toluene, 2 h

2: 1.) n-butyllithium / 1.) ether, hexanes, -78 deg C, 1 min, 2.) ether, hexanes, -78 deg C, 2 min

With n-butyllithium; potassium hexamethylsilazane;
DOI:10.1021/jo971591n

Reference yield:

: (S)-4-((Z)-2-Iodo-vinyl)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolane

: 200859-96-7
(1S,3R,4S)-3-(methoxymethoxy)-7,7-dimethyl-1-[(Z)-2-(phenylthio)vinyl]bicyclo[2.2.1]heptan-2-one

: 200859-97-8
(1S,2S,3R,4S)-2-((Z)-2-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-vinyl)-3-methoxymethoxy-7,7-dimethyl-1-((Z)-2-phenylsulfanyl-vinyl)-bicyclo[2.2.1]heptan-2-ol

Guidance literature:: With n-butyllithium; Yield given. Multistep reaction; 1.) ether, hexanes, -78 deg C, 1 min, 2.) ether, hexanes, -78 deg C, 2 min;
DOI:10.1021/jo971591n

Reference yield:

: 200859-97-8
(1S,2S,3R,4S)-2-((Z)-2-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-vinyl)-3-methoxymethoxy-7,7-dimethyl-1-((Z)-2-phenylsulfanyl-vinyl)-bicyclo[2.2.1]heptan-2-ol

: 1-((1S,2R,3S,5R,6S,7S,11R)-6,7-Dihydroxy-11-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-10,10-dimethyl-4-oxa-tricyclo[5.2.1.1^3,5]undec-3-yl)-ethanone

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) 18-crown-6, potassium hexamethyldisilazide / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 1 h

2: 77 percent / lithium aluminum hydride / diethyl ether / 2 h

4: 86 percent / potassium carbonate / methanol / 0.5 h / Ambient temperature

5: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

6: 66 percent / 18-crown-6, oxygen / tetrahydrofuran; toluene / 0.33 h

7: 96 percent / m-chloroperbenzoic acid, sodium bicarbonate / CH₂Cl₂ / 16 h

8: 56 percent / potassium hydroxide / dimethylsulfoxide; H₂O / 2 h / 55 °C

With potassium hydroxide; lithium aluminium tetrahydride; 18-crown-6 ether; oxygen; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene;
DOI:10.1021/jo971591n