(E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-en-1-ol

Base Information

Chemical Name:(E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-en-1-ol
CAS No.:914638-83-8
Molecular Formula:C₃₉H₄₆O₆
Molecular Weight:610.791
Hs Code.:

Synonyms:(E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-en-1-ol

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Chemical Property of (E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-en-1-ol

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Technology Process of (E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-en-1-ol

There total 18 articles about (E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-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: 95.0%

: 914638-81-6
tert-Butyl-diphenyl-[(E)-(3S,4S,7S,9R)-3,4,7-tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-enyloxy]-silane

: 914638-83-8
(E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-en-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 12h;
DOI:10.1016/j.tetlet.2006.08.035

Reference yield:

: 914638-92-9
(E)-(S)-4-(1,4-Dioxa-spiro[4.5]dec-2-yl)-but-2-en-1-ol

: 914638-83-8
(E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-en-1-ol

Guidance literature:: Multi-step reaction with 13 steps

1.1: 85 percent / cumene hydroperoxide; (iPrO)4Ti / (+)-DIPT / CH₂Cl₂ / 12 h / -20 °C

2.1: CCl₄; Ph₃P; NaHCO₃ / 1 h / Heating

2.2: LDA / tetrahydrofuran / 3 h / -78 - -40 °C

3.1: 80 percent / NaH / tetrahydrofuran / 6 h / 0 - 20 °C

4.1: 85 percent / CSA / methanol / 0.5 h / 20 °C

5.1: 75 percent / Et₃N / CH₂Cl₂ / 12 h / 0 - 20 °C

6.1: 90 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 - 20 °C

7.1: 75 percent / NaH / tetrahydrofuran / 12 h / 0 - 20 °C

8.1: 70 percent / n-BuLi / tetrahydrofuran / 3 h / -78 °C

9.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 20 °C

10.1: 80 percent / K-Selectride / tetrahydrofuran / 3 h / -78 °C

11.1: 95 percent / Red-Al / diethyl ether / 2 h / 0 - 20 °C

12.1: 75 percent / NaH / tetrahydrofuran; dimethylformamide / 4 h / 0 - 20 °C

13.1: 95 percent / TBAF / tetrahydrofuran / 12 h / 0 - 20 °C

With titanium(IV) isopropylate; tetrachloromethane; lithium aluminium tetrahydride; n-butyllithium; Cumene hydroperoxide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; potassium tri-sec-butyl-borohydride; Dess-Martin periodane; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; L-(+)-diisopropyl tartrate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Sharpless epoxidation;
DOI:10.1016/j.tetlet.2006.08.035

Reference yield:

: 914638-72-5
(E)-(S)-4-(1,4-Dioxa-spiro[4.5]dec-2-yl)-but-2-enoic acid ethyl ester

: 914638-83-8
(E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-en-1-ol

Guidance literature:: Multi-step reaction with 14 steps

1.1: 65 percent / LiAlH₄; AlCl₃ / diethyl ether / 6 h / 0 °C

2.1: 85 percent / cumene hydroperoxide; (iPrO)4Ti / (+)-DIPT / CH₂Cl₂ / 12 h / -20 °C

3.1: CCl₄; Ph₃P; NaHCO₃ / 1 h / Heating

3.2: LDA / tetrahydrofuran / 3 h / -78 - -40 °C

4.1: 80 percent / NaH / tetrahydrofuran / 6 h / 0 - 20 °C

5.1: 85 percent / CSA / methanol / 0.5 h / 20 °C

6.1: 75 percent / Et₃N / CH₂Cl₂ / 12 h / 0 - 20 °C

7.1: 90 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 - 20 °C

8.1: 75 percent / NaH / tetrahydrofuran / 12 h / 0 - 20 °C

9.1: 70 percent / n-BuLi / tetrahydrofuran / 3 h / -78 °C

10.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 20 °C

11.1: 80 percent / K-Selectride / tetrahydrofuran / 3 h / -78 °C

12.1: 95 percent / Red-Al / diethyl ether / 2 h / 0 - 20 °C

13.1: 75 percent / NaH / tetrahydrofuran; dimethylformamide / 4 h / 0 - 20 °C

14.1: 95 percent / TBAF / tetrahydrofuran / 12 h / 0 - 20 °C

With titanium(IV) isopropylate; tetrachloromethane; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; Cumene hydroperoxide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; potassium tri-sec-butyl-borohydride; Dess-Martin periodane; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; L-(+)-diisopropyl tartrate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 2.1: Sharpless epoxidation;
DOI:10.1016/j.tetlet.2006.08.035