(7S,8R,9S)-8-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-ol

Base Information

Chemical Name:(7S,8R,9S)-8-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-ol
CAS No.:860438-01-3
Molecular Formula:C₅₂H₇₂O₈Si
Molecular Weight:853.224
Hs Code.:

(7S,8R,9S)-8-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-ol

Synonyms:(7S,8R,9S)-8-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-ol

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Chemical Property of (7S,8R,9S)-8-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-ol

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Technology Process of (7S,8R,9S)-8-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-ol

There total 10 articles about (7S,8R,9S)-8-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-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: 90.0%

: 860437-76-9
(3S,4R,5S)-4-Benzyloxymethoxy-3-(tert-butyl-diphenyl-silanyloxy)-6-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-methyl-hexanal

: 20038-12-4
4-bromo-2-methylbut-1-ene

: 860438-01-3
(7S,8R,9S)-8-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-ol

Guidance literature:: 4-bromo-2-methylbut-1-ene; With magnesium; In tetrahydrofuran; for 45h; Heating;

(3S,4R,5S)-4-Benzyloxymethoxy-3-(tert-butyl-diphenyl-silanyloxy)-6-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-methyl-hexanal; In tetrahydrofuran; at -78 - -40 ℃; for 2.5h;
DOI:10.1021/ol0511833

Reference yield:

: 5-[4-(4-methoxy-benzyloxy)-butane-1-sulfonyl]-1-phenyl-1H-tetrazole

: 860438-01-3
(7S,8R,9S)-8-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 91 percent / KHMDS / tetrahydrofuran; toluene / 4 h / -78 °C

2.1: 95 percent / CSA / CH₂Cl₂; methanol / 3 h / 0 °C

3.1: 76 percent / AD-mix-α; (DHQ)2PHAL; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O

4.1: 85 percent / PPTS / 20 °C

5.1: 91 percent / Dess-Martin reagent; pyridine / CH₂Cl₂ / 6 h / 20 °C

6.1: Mg / tetrahydrofuran / 45 h / Heating

6.2: 90 percent / tetrahydrofuran / 2.5 h / -78 - -40 °C

With pyridine; AD-mix-α; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; Dess-Martin periodane; magnesium; In tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol; 6.2: Grignard reaction;
DOI:10.1021/ol0511833

Reference yield:

: 1-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-5-methyl-oct-7-en-4-ol

: 860438-01-3
(7S,8R,9S)-8-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 98 percent / DIPEA; tetrabutylammonium iodide / CH₂Cl₂ / 96 h

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 96 percent / PPh₃ / CH₂Cl₂ / 5 h / 20 °C

3.1: 91 percent / KHMDS / tetrahydrofuran; toluene / 4 h / -78 °C

4.1: 95 percent / CSA / CH₂Cl₂; methanol / 3 h / 0 °C

5.1: 76 percent / AD-mix-α; (DHQ)2PHAL; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O

6.1: 85 percent / PPTS / 20 °C

7.1: 91 percent / Dess-Martin reagent; pyridine / CH₂Cl₂ / 6 h / 20 °C

8.1: Mg / tetrahydrofuran / 45 h / Heating

8.2: 90 percent / tetrahydrofuran / 2.5 h / -78 - -40 °C

With pyridine; AD-mix-α; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; Dess-Martin periodane; ozone; magnesium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol; 8.2: Grignard reaction;
DOI:10.1021/ol0511833