(2R,3S,4aR,6S,8S,8aR)-6-(3-Benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-8-triisopropylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

Base Information

Chemical Name:(2R,3S,4aR,6S,8S,8aR)-6-(3-Benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-8-triisopropylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran
CAS No.:374638-57-0
Molecular Formula:C₃₇H₆₆O₅Si₂
Molecular Weight:647.099
Hs Code.:

(2R,3S,4aR,6S,8S,8aR)-6-(3-Benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-8-triisopropylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

Synonyms:(2R,3S,4aR,6S,8S,8aR)-6-(3-Benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-8-triisopropylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

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Chemical Property of (2R,3S,4aR,6S,8S,8aR)-6-(3-Benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-8-triisopropylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

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Technology Process of (2R,3S,4aR,6S,8S,8aR)-6-(3-Benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-8-triisopropylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

There total 19 articles about (2R,3S,4aR,6S,8S,8aR)-6-(3-Benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-8-triisopropylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran 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: 90.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 440333-82-4
(2S,3S,4aR,6S,8S,8aR)-6-(3-Benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-8-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-carbaldehyde

: 374638-57-0
(2R,3S,4aR,6S,8S,8aR)-6-(3-Benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-8-triisopropylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Methyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.166667h;

(2S,3S,4aR,6S,8S,8aR)-6-(3-Benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-8-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-carbaldehyde; In tetrahydrofuran; at 40 ℃; for 0.5h;
DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

: 131311-02-9
(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 374638-57-0
(2R,3S,4aR,6S,8S,8aR)-6-(3-Benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-8-triisopropylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Multi-step reaction with 18 steps

1.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

2.1: O₃ / CH₂Cl₂; methanol / -78 °C

2.2: 99 percent / PPh₃ / CH₂Cl₂; methanol / 0.5 h / 20 °C

3.1: diethyl ether; pentane / 5 h / -78 °C

3.2: 92 percent / aq. H₂O₂; aq. NaOH / diethyl ether; pentane; methanol / 1 h / 20 °C

4.1: 100 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

5.1: O₃ / CH₂Cl₂; methanol / -78 °C

5.2: 99 percent / PPh₃ / CH₂Cl₂; methanol / 1 h / 25 °C

6.1: 95 percent / CH₂Cl₂ / 12 h / 40 °C

7.1: 78 percent / K₂CO₃ / tetrahydrofuran; methanol / 5 h / 40 °C

8.1: 98 percent / 2,6-lutidine / dimethylformamide / 13 h / 60 °C

9.1: 96 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

10.1: DMSO; (COCl)2 / CH₂Cl₂ / 1.5 h / -78 °C

10.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

11.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

11.2: 2.8 g / tetrahydrofuran / 1 h

12.1: cyclohexene; BH₃*SMe₂ / tetrahydrofuran / 0.5 h / 0 °C

12.2: 94 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran / 1 h / 20 °C

13.1: KH / tetrahydrofuran / 0.67 h / 0 °C

13.2: 100 percent / tetrahydrofuran / 14 h / 20 °C

14.1: 99 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 22 h / 20 °C

15.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

16.1: 77 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 18 h / 0 °C

17.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

17.2: 100 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

18.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

18.2: 90 percent / tetrahydrofuran / 0.5 h / 40 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; oxalyl dichloride; dimethylsulfide borane complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; potassium hydride; potassium carbonate; ozone; dimethyl sulfoxide; cyclohexene; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane; 3.1: Brown's asymmetric allylboration / 6.1: Wittig reaction / 7.1: intramolecular hetero-Michael reaction / 10.1: Swern oxidation / 11.2: Wittig reaction / 17.1: Swern oxidation / 18.2: Wittig reaction;
DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

: 131311-03-0
tert-Butyl-((2R,4aR,6S,7R,8aS)-4a,6-dimethyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane

: 374638-57-0
(2R,3S,4aR,6S,8S,8aR)-6-(3-Benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-8-triisopropylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Multi-step reaction with 17 steps

1.1: O₃ / CH₂Cl₂; methanol / -78 °C

1.2: 99 percent / PPh₃ / CH₂Cl₂; methanol / 0.5 h / 20 °C

2.1: diethyl ether; pentane / 5 h / -78 °C

2.2: 92 percent / aq. H₂O₂; aq. NaOH / diethyl ether; pentane; methanol / 1 h / 20 °C

3.1: 100 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

4.1: O₃ / CH₂Cl₂; methanol / -78 °C

4.2: 99 percent / PPh₃ / CH₂Cl₂; methanol / 1 h / 25 °C

5.1: 95 percent / CH₂Cl₂ / 12 h / 40 °C

6.1: 78 percent / K₂CO₃ / tetrahydrofuran; methanol / 5 h / 40 °C

7.1: 98 percent / 2,6-lutidine / dimethylformamide / 13 h / 60 °C

8.1: 96 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

9.1: DMSO; (COCl)2 / CH₂Cl₂ / 1.5 h / -78 °C

9.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

10.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

10.2: 2.8 g / tetrahydrofuran / 1 h

11.1: cyclohexene; BH₃*SMe₂ / tetrahydrofuran / 0.5 h / 0 °C

11.2: 94 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran / 1 h / 20 °C

12.1: KH / tetrahydrofuran / 0.67 h / 0 °C

12.2: 100 percent / tetrahydrofuran / 14 h / 20 °C

13.1: 99 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 22 h / 20 °C

14.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

15.1: 77 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 18 h / 0 °C

16.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

16.2: 100 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

17.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

17.2: 90 percent / tetrahydrofuran / 0.5 h / 40 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; oxalyl dichloride; dimethylsulfide borane complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; potassium hydride; potassium carbonate; ozone; dimethyl sulfoxide; cyclohexene; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane; 2.1: Brown's asymmetric allylboration / 5.1: Wittig reaction / 6.1: intramolecular hetero-Michael reaction / 9.1: Swern oxidation / 10.2: Wittig reaction / 16.1: Swern oxidation / 17.2: Wittig reaction;
DOI:10.1016/S0040-4020(02)00039-X