2-[(2S,4R,6R,8S,9R,11R)-11-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

Base Information

Chemical Name:2-[(2S,4R,6R,8S,9R,11R)-11-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol
CAS No.:128478-22-8
Molecular Formula:C₂₈H₄₈O₅Si
Molecular Weight:492.772
Hs Code.:

Synonyms:2-[(2S,4R,6R,8S,9R,11R)-11-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

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Chemical Property of 2-[(2S,4R,6R,8S,9R,11R)-11-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

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Technology Process of 2-[(2S,4R,6R,8S,9R,11R)-11-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

There total 14 articles about 2-[(2S,4R,6R,8S,9R,11R)-11-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol 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: 89.0%

: 128459-57-4
((2R,4R,6R,8S,9R,11R)-11-Benzyloxy-8-isopropyl-9-methyl-2-vinyl-1,7-dioxa-spiro[5.5]undec-4-yloxy)-tert-butyl-dimethyl-silane

: 128478-22-8
2-[(2S,4R,6R,8S,9R,11R)-11-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

Guidance literature:: With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; Irradiation;
DOI:10.1016/S0040-4039(01)93836-5

Reference yield:

: 69143-05-1
(E)-4-methyl-pent-2-en-1-ol

: 128478-22-8
2-[(2S,4R,6R,8S,9R,11R)-11-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) t-BuOOH, Ti(i-PrO)4, DET; 2.) Me₂CuLi / 1.) CH₂Cl₂; 2.) Et₂O

2: 82 percent / Et₃N / CH₂Cl₂

3: 84 percent / Et₃N / CH₂Cl₂

4: 96 percent / NaI / butan-2-one / 80 °C

5: LDA, HMPA / tetrahydrofuran / -78 °C

6: tetrahydrofuran / -78 °C

7: K₂CO₃ / methanol

8: p-TSA / tetrahydrofuran; H₂O / 12 h / 65 °C

9: 3)>4 / tetrahydrofuran

10: NaBH₄ / 1,2-dimethoxy-ethane / 0 °C

11: 1.) Jones reag; 2.) lutidine / 1.) acetone; 2.) CH₂Cl₂

12: 89 percent / 9-BBN / tetrahydrofuran / Irradiation

With titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; tetrakiscopper(I); Jones reag; lutidine; N,N-Diethyl-3-methylbenzamide; lithium dimethylcuprate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; butanone;
DOI:10.1016/S0040-4039(01)93836-5

Reference yield:

: 3876-47-9,3876-46-8,60712-38-1,82335-99-7,97906-32-6,98391-91-4,103729-84-6,103729-88-0,129262-73-3
(2R*,3S*)-2,4-dimethyl-1,3-pentanediol

: 128478-22-8
2-[(2S,4R,6R,8S,9R,11R)-11-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

Guidance literature:: Multi-step reaction with 11 steps

1: 82 percent / Et₃N / CH₂Cl₂

2: 84 percent / Et₃N / CH₂Cl₂

3: 96 percent / NaI / butan-2-one / 80 °C

4: LDA, HMPA / tetrahydrofuran / -78 °C

5: tetrahydrofuran / -78 °C

6: K₂CO₃ / methanol

7: p-TSA / tetrahydrofuran; H₂O / 12 h / 65 °C

8: 3)>4 / tetrahydrofuran

9: NaBH₄ / 1,2-dimethoxy-ethane / 0 °C

10: 1.) Jones reag; 2.) lutidine / 1.) acetone; 2.) CH₂Cl₂

11: 89 percent / 9-BBN / tetrahydrofuran / Irradiation

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; tetrakiscopper(I); Jones reag; lutidine; potassium carbonate; toluene-4-sulfonic acid; triethylamine; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; butanone;
DOI:10.1016/S0040-4039(01)93836-5