(1E,6E,3S,4S)-4-(tert-butyldiphenylsilanyloxy)-7-[(4R,6R)-(4,6-dimethyl-[1,3]dioxan-2-yl)]-3-methoxymethoxy-1-[(2S)-(4-methyl-3,6-dihydro-2H-pyran-2-yl)]-hepta-1,6-diene

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Chemical Name:(1E,6E,3S,4S)-4-(tert-butyldiphenylsilanyloxy)-7-[(4R,6R)-(4,6-dimethyl-[1,3]dioxan-2-yl)]-3-methoxymethoxy-1-[(2S)-(4-methyl-3,6-dihydro-2H-pyran-2-yl)]-hepta-1,6-diene
CAS No.:379269-79-1
Molecular Formula:C₃₇H₅₂O₆Si
Molecular Weight:620.902
Hs Code.:

(1E,6E,3S,4S)-4-(tert-butyldiphenylsilanyloxy)-7-[(4R,6R)-(4,6-dimethyl-[1,3]dioxan-2-yl)]-3-methoxymethoxy-1-[(2S)-(4-methyl-3,6-dihydro-2H-pyran-2-yl)]-hepta-1,6-diene

Synonyms:(1E,6E,3S,4S)-4-(tert-butyldiphenylsilanyloxy)-7-[(4R,6R)-(4,6-dimethyl-[1,3]dioxan-2-yl)]-3-methoxymethoxy-1-[(2S)-(4-methyl-3,6-dihydro-2H-pyran-2-yl)]-hepta-1,6-diene

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Chemical Property of (1E,6E,3S,4S)-4-(tert-butyldiphenylsilanyloxy)-7-[(4R,6R)-(4,6-dimethyl-[1,3]dioxan-2-yl)]-3-methoxymethoxy-1-[(2S)-(4-methyl-3,6-dihydro-2H-pyran-2-yl)]-hepta-1,6-diene

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Technology Process of (1E,6E,3S,4S)-4-(tert-butyldiphenylsilanyloxy)-7-[(4R,6R)-(4,6-dimethyl-[1,3]dioxan-2-yl)]-3-methoxymethoxy-1-[(2S)-(4-methyl-3,6-dihydro-2H-pyran-2-yl)]-hepta-1,6-diene

There total 23 articles about (1E,6E,3S,4S)-4-(tert-butyldiphenylsilanyloxy)-7-[(4R,6R)-(4,6-dimethyl-[1,3]dioxan-2-yl)]-3-methoxymethoxy-1-[(2S)-(4-methyl-3,6-dihydro-2H-pyran-2-yl)]-hepta-1,6-diene 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: 98.0%

: 42075-32-1
(2R,4R)-pentanediol

: 379269-78-0
(2E,7E,5S,6S)-5-(tert-butyldiphenylsilanyloxy)-6-methoxymethoxy-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-octa-2,7-dienal

: 379269-79-1
(1E,6E,3S,4S)-4-(tert-butyldiphenylsilanyloxy)-7-[(4R,6R)-(4,6-dimethyl-[1,3]dioxan-2-yl)]-3-methoxymethoxy-1-[(2S)-(4-methyl-3,6-dihydro-2H-pyran-2-yl)]-hepta-1,6-diene

Guidance literature:: With montmorillonite K-10; In toluene; at 40 ℃; under 45.0036 Torr;
DOI:10.1021/jo026743f

Reference yield:

: 302554-92-3
(2E,5S,6S,7E)-5-(tert-butyldiphenylsilyloxy)-6-(methoxymethoxy)-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]octa-2,7-dien-1-ol

: 379269-79-1
(1E,6E,3S,4S)-4-(tert-butyldiphenylsilanyloxy)-7-[(4R,6R)-(4,6-dimethyl-[1,3]dioxan-2-yl)]-3-methoxymethoxy-1-[(2S)-(4-methyl-3,6-dihydro-2H-pyran-2-yl)]-hepta-1,6-diene

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / Dess-Martin reagent; NaHCO₃ / CH₂Cl₂ / 0.25 h / 20 °C

2: 98 percent / montmorillonite K-10 / toluene / 40 °C / 60.01 Torr

With montmorillonite K-10; sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; toluene;
DOI:10.1021/ja016752q

Reference yield:

: 206660-79-9
(S)-4-methyl-1-(trityloxy)pent-4-en-2-ol

: 379269-79-1
(1E,6E,3S,4S)-4-(tert-butyldiphenylsilanyloxy)-7-[(4R,6R)-(4,6-dimethyl-[1,3]dioxan-2-yl)]-3-methoxymethoxy-1-[(2S)-(4-methyl-3,6-dihydro-2H-pyran-2-yl)]-hepta-1,6-diene

Guidance literature:: Multi-step reaction with 12 steps

1.1: t-BuOK / tetrahydrofuran / 1 h / 20 - 45 °C

1.2: 92 percent / tetrahydrofuran / 1.5 h / 20 °C

2.1: Cl₂(PCy₃)2Ru=CHPh / tetrahydrofuran / 20 °C

3.1: 84 percent / HCl gas / CH₂Cl₂ / 0.5 h / -10 °C

4.1: Et₃N; pyr*SO₃ / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 - 5 °C

5.1: 81 percent / Et₃N; LiCl / tetrahydrofuran / 15 h / 0 °C

6.1: 94 percent / NaBH₄; CeCl₃*7H₂O / ethanol / 0.17 h / -78 °C

7.1: iPr₂NEt; TBAI / dimethylformamide / 16 h / 20 °C

8.1: 4.17 g / TsOH / methanol / 0.5 h / 20 °C

9.1: 98 percent / SO₃*pyridine; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 20 °C

10.1: 92 percent / NaH / tetrahydrofuran / 1.5 h / 20 °C

11.1: 89 percent / DIBALH / tetrahydrofuran; hexane / 0.75 h / -78 °C

12.1: 98 percent / montmorillonite K-10 / toluene / 40 °C / 45 Torr

With hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; pyridine-SO₃ complex; montmorillonite K-10; potassium tert-butylate; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; Grubbs catalyst first generation; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 4.1: Parikh-Doering oxidation / 9.1: Parikh-Doering oxidation / 10.1: Wittig-Horner-Emmons olefination;
DOI:10.1021/jo026743f