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

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Chemical Name:(7S,8R,9S)-8-Benzyloxymethoxy-7-hydroxy-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-one
CAS No.:860437-78-1
Molecular Formula:C₃₆H₅₂O₈
Molecular Weight:612.804
Hs Code.:

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

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

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

There total 12 articles about (7S,8R,9S)-8-Benzyloxymethoxy-7-hydroxy-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-one 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: 95.0%

: 860437-77-0
(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-one

: 860437-78-1
(7S,8R,9S)-8-Benzyloxymethoxy-7-hydroxy-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-one

Guidance literature:: With tetrabutyl ammonium fluoride; In water; acetic acid; at 50 ℃; for 48h;
DOI:10.1021/ol0511833

Reference yield:

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

: 860437-78-1
(7S,8R,9S)-8-Benzyloxymethoxy-7-hydroxy-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-one

Guidance literature:: Multi-step reaction with 8 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

7.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂; pyridine / 2 h / 20 °C

8.1: 95 percent / TBAF / H₂O; acetic acid / 48 h / 50 °C

With pyridine; AD-mix-α; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; Dess-Martin periodane; magnesium; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; 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

: 860437-78-1
(7S,8R,9S)-8-Benzyloxymethoxy-7-hydroxy-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-one

Guidance literature:: Multi-step reaction with 10 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

9.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂; pyridine / 2 h / 20 °C

10.1: 95 percent / TBAF / H₂O; acetic acid / 48 h / 50 °C

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