(E)-(S)-6-((1R,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-1-vinyl-bicyclo[3.2.1]oct-2-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-7-phenylsulfanyl-hept-5-enal

Base Information

Chemical Name:(E)-(S)-6-((1R,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-1-vinyl-bicyclo[3.2.1]oct-2-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-7-phenylsulfanyl-hept-5-enal
CAS No.:1027509-58-5
Molecular Formula:C₃₆H₅₈O₆SSi
Molecular Weight:647.004
Hs Code.:

(E)-(S)-6-((1R,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-1-vinyl-bicyclo[3.2.1]oct-2-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-7-phenylsulfanyl-hept-5-enal

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Chemical Property of (E)-(S)-6-((1R,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-1-vinyl-bicyclo[3.2.1]oct-2-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-7-phenylsulfanyl-hept-5-enal

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Technology Process of (E)-(S)-6-((1R,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-1-vinyl-bicyclo[3.2.1]oct-2-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-7-phenylsulfanyl-hept-5-enal

There total 22 articles about (E)-(S)-6-((1R,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-1-vinyl-bicyclo[3.2.1]oct-2-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-7-phenylsulfanyl-hept-5-enal 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:

: 1026577-65-0
(E)-(S)-6-((1R,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-1-vinyl-bicyclo[3.2.1]oct-2-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-7-phenylsulfanyl-hept-5-en-1-ol

: 1027509-58-5
(E)-(S)-6-((1R,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-1-vinyl-bicyclo[3.2.1]oct-2-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-7-phenylsulfanyl-hept-5-enal

Guidance literature:: With Dess-Martin periodane; In dichloromethane; Yield given; Ambient temperature;
DOI:10.1021/jo00098a009

Reference yield:

: 160714-21-6
(3R,3aR,7R,7aR)-7-Hydroxy-3-methyl-7a-prop-2-ynyl-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one

: 1027509-58-5
(E)-(S)-6-((1R,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-1-vinyl-bicyclo[3.2.1]oct-2-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-7-phenylsulfanyl-hept-5-enal

Guidance literature:: Multi-step reaction with 16 steps

1: 87 percent / NaAuCl₄*H₂O, H₂O / tetrahydrofuran / 60 °C

2: 86 percent / SmI₂, HMPA / tetrahydrofuran

3: (i-Pr)2NEt / CH₂Cl₂ / Ambient temperature

4: 1 N KOH / methanol / 80 °C

5: diethyl ether / Ambient temperature

6: Jones reagent / acetone / 0 °C

7: LiN(SiMe₃)2 / tetrahydrofuran / -78 °C

8: tetrahydrofuran / -20 °C

9: DIBAL / CH₂Cl₂ / -78 °C

10: Dess-Martin reagent / CH₂Cl₂ / Ambient temperature

11: tetrahydrofuran / Ambient temperature

12: n-BuLi, TMEDA / hexamethylphosphoric acid triamide; tetrahydrofuran

13: (PhS)2 / xylene / 160 °C

14: (i-Pr)2NEt / CH₂Cl₂ / 0 °C

15: DDQ, H₂O / CH₂Cl₂ / Ambient temperature

16: Dess-Martin reagent / CH₂Cl₂ / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; n-butyllithium; jones reagent; samarium diiodide; sodium tetrachloroaurate dihydrate; N,N,N,N,-tetramethylethylenediamine; water; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; diphenyldisulfane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; acetone; xylene;
DOI:10.1021/jo00098a009

Reference yield:

: 160714-20-5
(3R,3aR,7aR)-3-Methyl-7a-prop-2-ynyl-3a,7a-dihydro-3H,4H-isobenzofuran-1,7-dione

: 1027509-58-5
(E)-(S)-6-((1R,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-1-vinyl-bicyclo[3.2.1]oct-2-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-7-phenylsulfanyl-hept-5-enal

Guidance literature:: Multi-step reaction with 17 steps

1: 63 percent / NaBH₄, CeCl₃*7H₂O / methanol

2: 87 percent / NaAuCl₄*H₂O, H₂O / tetrahydrofuran / 60 °C

3: 86 percent / SmI₂, HMPA / tetrahydrofuran

4: (i-Pr)2NEt / CH₂Cl₂ / Ambient temperature

5: 1 N KOH / methanol / 80 °C

6: diethyl ether / Ambient temperature

7: Jones reagent / acetone / 0 °C

8: LiN(SiMe₃)2 / tetrahydrofuran / -78 °C

9: tetrahydrofuran / -20 °C

10: DIBAL / CH₂Cl₂ / -78 °C

11: Dess-Martin reagent / CH₂Cl₂ / Ambient temperature

12: tetrahydrofuran / Ambient temperature

13: n-BuLi, TMEDA / hexamethylphosphoric acid triamide; tetrahydrofuran

14: (PhS)2 / xylene / 160 °C

15: (i-Pr)2NEt / CH₂Cl₂ / 0 °C

16: DDQ, H₂O / CH₂Cl₂ / Ambient temperature

17: Dess-Martin reagent / CH₂Cl₂ / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; jones reagent; samarium diiodide; cerium(III) chloride; sodium tetrachloroaurate dihydrate; N,N,N,N,-tetramethylethylenediamine; water; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; diphenyldisulfane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; acetone; xylene;
DOI:10.1021/jo00098a009