(1S,2S,3R,4S)-2-{(Z)-2-[(2R,3S)-3-(benzyloxy)-2-{2-(tert-butyldimethylsiloxy)ethyl}-3-oxetanyl]vinyl}-3-[(p-methoxybenzyl)oxy]-7,7-dimethyl-1-[(Z)-2-(phenylthio)vinyl]bicyclo[2.2.1]heptan-2-ol

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Chemical Name:(1S,2S,3R,4S)-2-{(Z)-2-[(2R,3S)-3-(benzyloxy)-2-{2-(tert-butyldimethylsiloxy)ethyl}-3-oxetanyl]vinyl}-3-[(p-methoxybenzyl)oxy]-7,7-dimethyl-1-[(Z)-2-(phenylthio)vinyl]bicyclo[2.2.1]heptan-2-ol
CAS No.:213913-04-3
Molecular Formula:C₄₅H₆₀O₆SSi
Molecular Weight:757.119
Hs Code.:

(1S,2S,3R,4S)-2-{(Z)-2-[(2R,3S)-3-(benzyloxy)-2-{2-(tert-butyldimethylsiloxy)ethyl}-3-oxetanyl]vinyl}-3-[(p-methoxybenzyl)oxy]-7,7-dimethyl-1-[(Z)-2-(phenylthio)vinyl]bicyclo[2.2.1]heptan-2-ol

Synonyms:(1S,2S,3R,4S)-2-{(Z)-2-[(2R,3S)-3-(benzyloxy)-2-{2-(tert-butyldimethylsiloxy)ethyl}-3-oxetanyl]vinyl}-3-[(p-methoxybenzyl)oxy]-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-{(Z)-2-[(2R,3S)-3-(benzyloxy)-2-{2-(tert-butyldimethylsiloxy)ethyl}-3-oxetanyl]vinyl}-3-[(p-methoxybenzyl)oxy]-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-{(Z)-2-[(2R,3S)-3-(benzyloxy)-2-{2-(tert-butyldimethylsiloxy)ethyl}-3-oxetanyl]vinyl}-3-[(p-methoxybenzyl)oxy]-7,7-dimethyl-1-[(Z)-2-(phenylthio)vinyl]bicyclo[2.2.1]heptan-2-ol

There total 11 articles about (1S,2S,3R,4S)-2-{(Z)-2-[(2R,3S)-3-(benzyloxy)-2-{2-(tert-butyldimethylsiloxy)ethyl}-3-oxetanyl]vinyl}-3-[(p-methoxybenzyl)oxy]-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: 80.0%

: 213912-96-0
[2-{(2R,3S)-3-(benzyloxy)-3-[(Z)-2-iodovinyl]-2-oxetanyl}ethoxy]-tert-butyldimethylsilane

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

: 213913-04-3
(1S,2S,3R,4S)-2-{(Z)-2-[(2R,3S)-3-(benzyloxy)-2-{2-(tert-butyldimethylsiloxy)ethyl}-3-oxetanyl]vinyl}-3-[(p-methoxybenzyl)oxy]-7,7-dimethyl-1-[(Z)-2-(phenylthio)vinyl]bicyclo[2.2.1]heptan-2-ol

Guidance literature:: With tert.-butyl lithium; In diethyl ether; at -110 ℃;
DOI:10.1021/jo981059f

Reference yield: 80.0%

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

: C₂₀H₃₁LiO₃Si

: 213913-04-3
(1S,2S,3R,4S)-2-{(Z)-2-[(2R,3S)-3-(benzyloxy)-2-{2-(tert-butyldimethylsiloxy)ethyl}-3-oxetanyl]vinyl}-3-[(p-methoxybenzyl)oxy]-7,7-dimethyl-1-[(Z)-2-(phenylthio)vinyl]bicyclo[2.2.1]heptan-2-ol

Guidance literature:: With n-butyllithium; In diethyl ether; toluene; at -110 ℃; for 0.5h;
DOI:10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187<3.0.CO;2-2

Reference yield:

: 189165-94-4
(3aR,5R,6S,6aR)-5-<2-(tert-butyldimethylsiloxy)ethyl>-tetrahydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-ol

: 213913-04-3
(1S,2S,3R,4S)-2-{(Z)-2-[(2R,3S)-3-(benzyloxy)-2-{2-(tert-butyldimethylsiloxy)ethyl}-3-oxetanyl]vinyl}-3-[(p-methoxybenzyl)oxy]-7,7-dimethyl-1-[(Z)-2-(phenylthio)vinyl]bicyclo[2.2.1]heptan-2-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

2.1: diethyl ether; tetrahydrofuran / 0.33 h / -78 °C

3.1: 96 percent / NaH; tetra-n-butylammonium iodide / dimethylformamide; tetrahydrofuran / 0 - 20 °C

4.1: 81 percent / TiCl₄ / CH₂Cl₂ / 12 h / -78 - 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 0.33 h

5.2: 76 percent / NaBH₄ / methanol / 0.5 h / 0 °C

6.1: 74 percent / potassium hexamethyldisilazide; N-phenyltriflimide / tetrahydrofuran; toluene / 0.5 h / -78 °C

7.1: OsO₄; NMO; NaIO₄ / tetrahydrofuran; H₂O / 23.5 h / pH 7

8.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.17 h / -78 °C

9.1: n-BuLi / diethyl ether; toluene / -110 °C

10.1: 80 percent / n-BuLi / diethyl ether; toluene / 0.5 h / -110 °C

With sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; N,N-phenylbistrifluoromethane-sulfonimide; sodium hexamethyldisilazane; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Oxidation / 2.1: Addition / 3.1: Alkylation / 4.1: deacetalization / 5.1: Oxidation / 5.2: Reduction / 6.1: Cyclization / 7.1: Oxidation / 8.1: Wittig condensation / 9.1: Metallation / 10.1: Addition;
DOI:10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187<3.0.CO;2-2