(2S,3R,4S,6S)-3-Benzyloxymethoxy-1-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-9-ene-4,6-diol

Base Information

Chemical Name:(2S,3R,4S,6S)-3-Benzyloxymethoxy-1-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-9-ene-4,6-diol
CAS No.:860438-02-4
Molecular Formula:C₃₆H₅₄O₈
Molecular Weight:614.82
Hs Code.:

Synonyms:(2S,3R,4S,6S)-3-Benzyloxymethoxy-1-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-9-ene-4,6-diol

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Chemical Property of (2S,3R,4S,6S)-3-Benzyloxymethoxy-1-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-9-ene-4,6-diol

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Technology Process of (2S,3R,4S,6S)-3-Benzyloxymethoxy-1-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-9-ene-4,6-diol

There total 13 articles about (2S,3R,4S,6S)-3-Benzyloxymethoxy-1-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-9-ene-4,6-diol 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: 94.0%

: 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

: 860438-02-4
(2S,3R,4S,6S)-3-Benzyloxymethoxy-1-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-9-ene-4,6-diol

Guidance literature:: With sodium tetrahydroborate; diethyl methoxy borane; In tetrahydrofuran; methanol; at -78 - 20 ℃;
DOI:10.1021/ol0511833

Reference yield:

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

: 860438-02-4
(2S,3R,4S,6S)-3-Benzyloxymethoxy-1-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-9-ene-4,6-diol

Guidance literature:: Multi-step reaction with 9 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

9.1: 94 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / -78 - 20 °C

With pyridine; sodium tetrahydroborate; AD-mix-α; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; camphor-10-sulfonic acid; diethyl methoxy borane; 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

: 860438-02-4
(2S,3R,4S,6S)-3-Benzyloxymethoxy-1-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-9-ene-4,6-diol

Guidance literature:: Multi-step reaction with 11 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

11.1: 94 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / -78 - 20 °C

With pyridine; sodium tetrahydroborate; AD-mix-α; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; camphor-10-sulfonic acid; diethyl methoxy borane; 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