(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

Base Information

Chemical Name:(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
CAS No.:213912-87-9
Molecular Formula:C₅₅H₇₄O₉SSi
Molecular Weight:939.339
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 9 articles about (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 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: 71.0%

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

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

: 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:: With n-butyllithium; In diethyl ether; at -78 - -40 ℃;
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

Reference yield:

: 217819-76-6
(2S,3R)-2-(benzyloxy)-3-<(p-methoxybenzyl)oxy>-2-<<(p-methoxybenzyl)oxy>methyl>-4-pentenal

: 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:: Multi-step reaction with 8 steps

1.1: LiAlH₄ / diethyl ether / 0.5 h

2.1: 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h

3.1: 96 percent / 9-BBN; NaOH; H₂O₂ / tetrahydrofuran; H₂O / 15 h

4.1: imidazole / dimethylformamide / 1 h

5.1: DIBAH-L / CH₂Cl₂; hexane / 1 h / -78 °C

6.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

7.1: 85 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C

8.1: n-BuLi / diethyl ether; hexane / 0.02 h / -78 °C

8.2: 71 percent / diethyl ether / 1 h / -78 - -40 °C

With 1H-imidazole; dmap; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Acylation / 3.1: hydroboration / 4.1: Etherification / 5.1: Reduction / 6.1: Oxidation / 7.1: Wittig condensation / 8.1: Metallation / 8.2: Addition;
DOI:10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187<3.0.CO;2-2