(Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene

Base Information

Chemical Name:(Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene
CAS No.:475641-59-9
Molecular Formula:C₂₉H₅₀O₅Si₂
Molecular Weight:534.884
Hs Code.:

(Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene

Synonyms:(Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene

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Chemical Property of (Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene

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Technology Process of (Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene

There total 19 articles about (Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene 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: 98.0%

: 475641-89-5
(2R,4S,5R)-4-Allyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxane

: 475641-59-9
(Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene

Guidance literature:: Grubbs catalyst first generation; In dichloromethane; for 3h; Heating;
DOI:10.1055/s-2002-33527

Reference yield:

: 83938-00-5
((2R,3S,6S)-3-acetoxy-6-cyano-3,6-dihydro-2H-pyran-2-yl)methyl acetate

: 475641-59-9
(Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene

Guidance literature:: Multi-step reaction with 18 steps

1.1: Amberlyst 15 / methanol / 24 h / Heating

2.1: Amberlyst 15 / CHCl₃ / 22.5 h

3.1: 100 percent / aq. OsO₄; NMO / dioxane / 96 h / 20 °C

4.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 72 h / 0 - 22 °C

5.1: DIBALH / CH₂Cl₂ / 0.2 h / -78 °C

6.1: aq. HCl / CH₂Cl₂ / 16 h / 22 °C

7.1: 79 percent / CH₂Cl₂ / 3.83 h / -78 - -20 °C

8.1: 95 percent / TBAF / tetrahydrofuran / 22 °C

9.1: aq. NaIO₄ / dioxane / 22 °C

10.1: NaBH₄ / methanol / 0 °C

11.1: 98 percent / benzene / Heating

12.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 21 - 23 °C

13.1: aq. H₂O₂ / ethyl acetate / 2 h / 21 - 23 °C

14.1: 2,6-lutidine / CH₂Cl₂ / 21 - 25 °C

15.1: 96 percent / dimethylsulfoxide / 23 - 25 °C

16.1: 88 percent / DIBALH / CH₂Cl₂ / -78 °C

17.1: NaHMDS / tetrahydrofuran / 2 h / 22 °C

17.2: 99 percent / tetrahydrofuran / 4 h / -78 - 23 °C

18.1: 98 percent / (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 3 h / Heating

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; Amberlyst 15; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; Grubbs catalyst first generation; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; dimethyl sulfoxide; ethyl acetate; benzene; 17.2: Wittig reaction;
DOI:10.1055/s-2002-33527

Reference yield:

: 88180-36-3
2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide

: 475641-59-9
(Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene

Guidance literature:: Multi-step reaction with 17 steps

1.1: Amberlyst 15 / CHCl₃ / 22.5 h

2.1: 100 percent / aq. OsO₄; NMO / dioxane / 96 h / 20 °C

3.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 72 h / 0 - 22 °C

4.1: DIBALH / CH₂Cl₂ / 0.2 h / -78 °C

5.1: aq. HCl / CH₂Cl₂ / 16 h / 22 °C

6.1: 79 percent / CH₂Cl₂ / 3.83 h / -78 - -20 °C

7.1: 95 percent / TBAF / tetrahydrofuran / 22 °C

8.1: aq. NaIO₄ / dioxane / 22 °C

9.1: NaBH₄ / methanol / 0 °C

10.1: 98 percent / benzene / Heating

11.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 21 - 23 °C

12.1: aq. H₂O₂ / ethyl acetate / 2 h / 21 - 23 °C

13.1: 2,6-lutidine / CH₂Cl₂ / 21 - 25 °C

14.1: 96 percent / dimethylsulfoxide / 23 - 25 °C

15.1: 88 percent / DIBALH / CH₂Cl₂ / -78 °C

16.1: NaHMDS / tetrahydrofuran / 2 h / 22 °C

16.2: 99 percent / tetrahydrofuran / 4 h / -78 - 23 °C

17.1: 98 percent / (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 3 h / Heating

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; Amberlyst 15; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; Grubbs catalyst first generation; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; dimethyl sulfoxide; ethyl acetate; benzene; 16.2: Wittig reaction;
DOI:10.1055/s-2002-33527