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

Base Information

Chemical Name:(1S,3R,4S)-3-(methoxymethoxy)-7,7-dimethyl-1-[(Z)-2-(phenylthio)vinyl]bicyclo[2.2.1]heptan-2-one
CAS No.:200859-96-7
Molecular Formula:C₁₉H₂₄O₃S
Molecular Weight:332.464
Hs Code.:

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

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Chemical Property of (1S,3R,4S)-3-(methoxymethoxy)-7,7-dimethyl-1-[(Z)-2-(phenylthio)vinyl]bicyclo[2.2.1]heptan-2-one

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Technology Process of (1S,3R,4S)-3-(methoxymethoxy)-7,7-dimethyl-1-[(Z)-2-(phenylthio)vinyl]bicyclo[2.2.1]heptan-2-one

There total 2 articles about (1S,3R,4S)-3-(methoxymethoxy)-7,7-dimethyl-1-[(Z)-2-(phenylthio)vinyl]bicyclo[2.2.1]heptan-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:

: 13884-92-9
phenylthiomethyl triphenylphosphonium chloride

: 162790-67-2
(1R,3R,4S)-3-Methoxymethoxy-7,7-dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carbaldehyde

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

: (1S,3R,4S)-3-Methoxymethoxy-7,7-dimethyl-1-((E)-2-phenylsulfanyl-vinyl)-bicyclo[2.2.1]heptan-2-one

Guidance literature:: With potassium hexamethylsilazane; Yield given. Multistep reaction. Yields of byproduct given; 1.) toluene, THF, 0 deg C, 30 min, 2.) THF, toluene, 2 h;
DOI:10.1021/jo971591n

Reference yield:

: 34884-33-8,91076-05-0
(phenylthio)-methylenetriphenylphosphorane

: 162790-67-2
(1R,3R,4S)-3-Methoxymethoxy-7,7-dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carbaldehyde

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

: (1S,3R,4S)-3-Methoxymethoxy-7,7-dimethyl-1-((E)-2-phenylsulfanyl-vinyl)-bicyclo[2.2.1]heptan-2-one

Guidance literature:: Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1021/jo981059f

Reference yield: 71.0%

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

: 213912-82-4
{[(3R,4S,5Z)-4-(benzyloxy)-6-iodo-3-[(p-methoxybenzyl)oxy]-4-{[(p-methoxybenzyl)oxy]methyl}-5-hexenyl]oxy}-tert-butyldimethylsilane

: 213912-87-9
(1S,2S,3R,4S)-2-{(1Z,3S,4R)-3-(benzyloxy)-6-(tert-butyldimethylsiloxy)-4-[(p-methoxybenzyl)oxy]-3-[{(p-methoxybenzyl)oxy}methyl]-1-hexenyl}-3-(methoxymethoxy)-7,7-dimethyl-1-[(Z)-2-(phenylthio)vinyl]bicyclo[2.2.1]heptan-2-ol

Guidance literature:: {[(3R,4S,5Z)-4-(benzyloxy)-6-iodo-3-[(p-methoxybenzyl)oxy]-4-{[(p-methoxybenzyl)oxy]methyl}-5-hexenyl]oxy}-tert-butyldimethylsilane; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 0.0166667h;

(1S,3R,4S)-3-(methoxymethoxy)-7,7-dimethyl-1-[(Z)-2-(phenylthio)vinyl]bicyclo[2.2.1]heptan-2-one; In diethyl ether; at -78 - -40 ℃; for 1h; Further stages.;
DOI:10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187<3.0.CO;2-2