(2S,3R,5S,7R,8R)-3,7-Dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-en-1-ol

Base Information

Chemical Name:(2S,3R,5S,7R,8R)-3,7-Dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-en-1-ol
CAS No.:651748-28-6
Molecular Formula:C₂₄H₄₀O₉
Molecular Weight:472.576
Hs Code.:

Synonyms:(2S,3R,5S,7R,8R)-3,7-Dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-en-1-ol

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Chemical Property of (2S,3R,5S,7R,8R)-3,7-Dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-en-1-ol

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Technology Process of (2S,3R,5S,7R,8R)-3,7-Dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-en-1-ol

There total 11 articles about (2S,3R,5S,7R,8R)-3,7-Dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-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: 96.0%

: 651748-27-5
tert-Butyl-[(2S,3R,5S,7R,8R)-3,7-dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-enyloxy]-diphenyl-silane

: 651748-28-6
(2S,3R,5S,7R,8R)-3,7-Dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-en-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ol036058a

Reference yield:

: 1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-but-3-en-1-ol

: 651748-28-6
(2S,3R,5S,7R,8R)-3,7-Dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-en-1-ol

Guidance literature:: Multi-step reaction with 11 steps

1: KOH / dimethylsulfoxide / 20 °C

2: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 °C

3: diethyl ether / -78 °C

4: 92 percent / TBAI; NaH / tetrahydrofuran / Heating

5: 96 percent / TsOH / methanol / 20 °C

6: 100 percent / DMAP; Et₃N / CH₂Cl₂ / 20 °C

7: 91 percent Turnov_. / iPr₂NEt / CH₂Cl₂ / 20 °C

8: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 °C

9: 85 percent / NaH / tetrahydrofuran / 20 °C

10: 96 percent / TBAF / tetrahydrofuran / 20 °C

With dmap; potassium hydroxide; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; 8: Johnson-Lemieux oxidation;
DOI:10.1021/ol036058a

Reference yield:

: 651748-11-7
(R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methoxy-propionaldehyde

: 651748-28-6
(2S,3R,5S,7R,8R)-3,7-Dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-en-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1: diethyl ether / -78 °C

2: 92 percent / TBAI; NaH / tetrahydrofuran / Heating

3: 96 percent / TsOH / methanol / 20 °C

4: 100 percent / DMAP; Et₃N / CH₂Cl₂ / 20 °C

5: 91 percent Turnov_. / iPr₂NEt / CH₂Cl₂ / 20 °C

6: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 °C

7: 85 percent / NaH / tetrahydrofuran / 20 °C

8: 96 percent / TBAF / tetrahydrofuran / 20 °C

With dmap; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 6: Johnson-Lemieux oxidation;
DOI:10.1021/ol036058a