(2S,3R,3aR,3bS,6S,6aS,7aR)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6a-trimethyl-3-trityloxymethyl-decahydro-cyclopenta[a]pentalene-3,3a-diol

Base Information

Chemical Name:(2S,3R,3aR,3bS,6S,6aS,7aR)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6a-trimethyl-3-trityloxymethyl-decahydro-cyclopenta[a]pentalene-3,3a-diol
CAS No.:110990-37-9
Molecular Formula:C₄₆H₆₈O₅Si₂
Molecular Weight:757.214
Hs Code.:

(2S,3R,3aR,3bS,6S,6aS,7aR)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6a-trimethyl-3-trityloxymethyl-decahydro-cyclopenta[a]pentalene-3,3a-diol

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Chemical Property of (2S,3R,3aR,3bS,6S,6aS,7aR)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6a-trimethyl-3-trityloxymethyl-decahydro-cyclopenta[a]pentalene-3,3a-diol

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3R,3aR,3bS,6S,6aS,7aR)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6a-trimethyl-3-trityloxymethyl-decahydro-cyclopenta[a]pentalene-3,3a-diol

There total 14 articles about (2S,3R,3aR,3bS,6S,6aS,7aR)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6a-trimethyl-3-trityloxymethyl-decahydro-cyclopenta[a]pentalene-3,3a-diol 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:

: 76-83-5
trityl chloride

: 110990-37-9
(2S,3R,3aR,3bS,6S,6aS,7aR)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6a-trimethyl-3-trityloxymethyl-decahydro-cyclopenta[a]pentalene-3,3a-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / 4-DMAP / dimethylformamide / 70 °C

2: 94 percent / act. MnO₂ / CHCl₃ / Ambient temperature

3: 81 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / -50 °C

4: 75 percent / L-Selectride / tetrahydrofuran / 0 °C

5: 99 percent / imidazole / dimethylformamide / Ambient temperature

6: 1.) osmium tetroxide, 2.) aq. NaHSO₃ / 1.) pyridine, 40 deg C, 2.) 70 deg C

With 1H-imidazole; dmap; manganese(IV) oxide; osmium(VIII) oxide; boron trifluoride diethyl etherate; L-Selectride; sodium hydrogensulfite; In tetrahydrofuran; diethyl ether; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)85180-1

Reference yield:

: 54931-38-3,101198-90-7,134053-16-0
(1R*,5R*)-5,8-dimethyl-cis-bicyclo<3.3.0>oct-7-en-2-one

: 110990-37-9
(2S,3R,3aR,3bS,6S,6aS,7aR)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6a-trimethyl-3-trityloxymethyl-decahydro-cyclopenta[a]pentalene-3,3a-diol

Guidance literature:: Multi-step reaction with 13 steps

1: 1.) LDA / 1.) THF, -78 deg C,

2: 90 percent / 30 percent aq. perchloric acid / diethyl ether / Ambient temperature

3: 85 percent / sodium ethoxide / ethanol / Ambient temperature

4: 70 percent / NaBH₄, CeCl₃*7H₂O / methanol

5: 98 percent / imidazole / dimethylformamide / Ambient temperature

6: 60 percent / CrO₃, 3,5-DMP / CH₂Cl₂ / -25 °C

7: 85 percent / DIBAH / toluene

8: 95 percent / 4-DMAP / dimethylformamide / 70 °C

9: 94 percent / act. MnO₂ / CHCl₃ / Ambient temperature

10: 81 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / -50 °C

11: 75 percent / L-Selectride / tetrahydrofuran / 0 °C

12: 99 percent / imidazole / dimethylformamide / Ambient temperature

13: 1.) osmium tetroxide, 2.) aq. NaHSO₃ / 1.) pyridine, 40 deg C, 2.) 70 deg C

With 1H-imidazole; chromium(VI) oxide; dmap; manganese(IV) oxide; sodium tetrahydroborate; osmium(VIII) oxide; perchloric acid; cerium(III) chloride; boron trifluoride diethyl etherate; sodium ethanolate; L-Selectride; diisobutylaluminium hydride; sodium hydrogensulfite; 3,5-Dimethylphenol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(00)85180-1

Reference yield:

: 110990-28-8,134053-17-1
(3bS,6aR,7aS)-4,6a-Dimethyl-2-oxo-2,3b,6,6a,7,7a-hexahydro-1H-cyclopenta[a]pentalene-3-carboxylic acid ethyl ester

: 110990-37-9
(2S,3R,3aR,3bS,6S,6aS,7aR)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6a-trimethyl-3-trityloxymethyl-decahydro-cyclopenta[a]pentalene-3,3a-diol

Guidance literature:: Multi-step reaction with 10 steps

1: 70 percent / NaBH₄, CeCl₃*7H₂O / methanol

2: 98 percent / imidazole / dimethylformamide / Ambient temperature

3: 60 percent / CrO₃, 3,5-DMP / CH₂Cl₂ / -25 °C

4: 85 percent / DIBAH / toluene

5: 95 percent / 4-DMAP / dimethylformamide / 70 °C

6: 94 percent / act. MnO₂ / CHCl₃ / Ambient temperature

7: 81 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / -50 °C

8: 75 percent / L-Selectride / tetrahydrofuran / 0 °C

9: 99 percent / imidazole / dimethylformamide / Ambient temperature

10: 1.) osmium tetroxide, 2.) aq. NaHSO₃ / 1.) pyridine, 40 deg C, 2.) 70 deg C

With 1H-imidazole; chromium(VI) oxide; dmap; manganese(IV) oxide; sodium tetrahydroborate; osmium(VIII) oxide; cerium(III) chloride; boron trifluoride diethyl etherate; L-Selectride; diisobutylaluminium hydride; sodium hydrogensulfite; 3,5-Dimethylphenol; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(00)85180-1