(E)-(2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-{(3aS,4S,7S,7aR)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-3-methyl-hex-4-en-1-ol

Base Information

Chemical Name:(E)-(2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-{(3aS,4S,7S,7aR)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-3-methyl-hex-4-en-1-ol
CAS No.:115118-88-2
Molecular Formula:C₃₉H₆₂O₆Si₂
Molecular Weight:683.089
Hs Code.:

(E)-(2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-{(3aS,4S,7S,7aR)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-3-methyl-hex-4-en-1-ol

Synonyms:(E)-(2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-{(3aS,4S,7S,7aR)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-3-methyl-hex-4-en-1-ol

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Chemical Property of (E)-(2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-{(3aS,4S,7S,7aR)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-3-methyl-hex-4-en-1-ol

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Technology Process of (E)-(2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-{(3aS,4S,7S,7aR)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-3-methyl-hex-4-en-1-ol

There total 17 articles about (E)-(2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-{(3aS,4S,7S,7aR)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-3-methyl-hex-4-en-1-ol 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: 77.0%

: 107148-27-6
<3aS-<3aα,4α,7aα,7α(3E,2R^*)>>-6-oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-yl>-2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-4-hexenoic acid methyl ester

: 115118-88-2
(E)-(2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-{(3aS,4S,7S,7aR)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-3-methyl-hex-4-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -20 ℃; for 0.5h;
DOI:10.1021/jo00253a021

Reference yield:

: (2S,3S)-2-(2-Hydroxy-ethyl)-3,6-dihydro-2H-pyran-3-ol

: 115118-88-2
(E)-(2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-{(3aS,4S,7S,7aR)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-3-methyl-hex-4-en-1-ol

Guidance literature:: Multi-step reaction with 10 steps

1: pyridine / 2 h / 0 - 20 °C

2: 100 percent / xylene / 12 h / Heating

3: 90 percent / N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 24 h / Ambient temperature

4: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature

5: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C

6: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH₂Cl₂, -100 deg C, 1 h

7: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH₂Cl₂ / Ambient temperature

8: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C

9: diethyl ether / 0 °C

10: 77 percent / diisobutylaluminium hydride / CH₂Cl₂; hexane / 0.5 h / -20 °C

With pyridine; dmap; osmium(VIII) oxide; chloro-trimethyl-silane; diisobutylaluminium hydride; toluene-4-sulfonic acid; copper(II) sulfate; magnesium; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetone; xylene;
DOI:10.1021/jo00253a021

Reference yield:

: 115118-80-4
2-{(3S,4R,5R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide

: 115118-88-2
(E)-(2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-{(3aS,4S,7S,7aR)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-3-methyl-hex-4-en-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature

2: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C

3: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH₂Cl₂, -100 deg C, 1 h

4: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH₂Cl₂ / Ambient temperature

5: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C

6: diethyl ether / 0 °C

7: 77 percent / diisobutylaluminium hydride / CH₂Cl₂; hexane / 0.5 h / -20 °C

With pyridine; dmap; chloro-trimethyl-silane; diisobutylaluminium hydride; toluene-4-sulfonic acid; copper(II) sulfate; magnesium; dicyclohexyl-carbodiimide; zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/jo00253a021