(3Z,10E,12E)-3-methyl-14-tert-butyldiphenylsiloxy-7,7-bis(methoxycarbonyl)-1-tetrahydropyranyloxy-tetradeca-3,10,12-triene

Base Information

Chemical Name:(3Z,10E,12E)-3-methyl-14-tert-butyldiphenylsiloxy-7,7-bis(methoxycarbonyl)-1-tetrahydropyranyloxy-tetradeca-3,10,12-triene
CAS No.:173656-68-3
Molecular Formula:C₄₀H₅₆O₇Si
Molecular Weight:676.966
Hs Code.:

Synonyms:(3Z,10E,12E)-3-methyl-14-tert-butyldiphenylsiloxy-7,7-bis(methoxycarbonyl)-1-tetrahydropyranyloxy-tetradeca-3,10,12-triene

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Chemical Property of (3Z,10E,12E)-3-methyl-14-tert-butyldiphenylsiloxy-7,7-bis(methoxycarbonyl)-1-tetrahydropyranyloxy-tetradeca-3,10,12-triene

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Technology Process of (3Z,10E,12E)-3-methyl-14-tert-butyldiphenylsiloxy-7,7-bis(methoxycarbonyl)-1-tetrahydropyranyloxy-tetradeca-3,10,12-triene

There total 11 articles about (3Z,10E,12E)-3-methyl-14-tert-butyldiphenylsiloxy-7,7-bis(methoxycarbonyl)-1-tetrahydropyranyloxy-tetradeca-3,10,12-triene 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: 66.0%

: 144344-22-9
Methanesulfonic acid (Z)-4-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl ester

: 173536-84-0
(E,E)-8-tert-butyldiphenylsiloxy-1,1-bis(methoxycarbonyl)-4,6-octadiene

: 173656-68-3
(3Z,10E,12E)-3-methyl-14-tert-butyldiphenylsiloxy-7,7-bis(methoxycarbonyl)-1-tetrahydropyranyloxy-tetradeca-3,10,12-triene

Guidance literature:: With sodium hydride; potassium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; at 70 ℃;
DOI:10.1016/S0040-4039(00)79137-4

Reference yield:

: 149311-09-1
(2E,4E)-7-(Tetrahydro-pyran-2-yloxy)-hepta-2,4-dien-1-ol

: 173656-68-3
(3Z,10E,12E)-3-methyl-14-tert-butyldiphenylsiloxy-7,7-bis(methoxycarbonyl)-1-tetrahydropyranyloxy-tetradeca-3,10,12-triene

Guidance literature:: Multi-step reaction with 5 steps

1: imidazole / tetrahydrofuran / 1 h / Ambient temperature

2: pyridinium-p-toluenesulfonate / propan-2-ol / 1 h / Heating

3: 100 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4: 1.) NaH, 2.) KI / 1.) DMF, room t., 2.) DMF, THF, 70-75 deg C, 15 h

5: 1.) NaH, 2.) KI / 1.) DMF, 1 h, 35-40 deg C, 2.) DMF, THF, 70 deg C, 12 h

With 1H-imidazole; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; potassium iodide; In tetrahydrofuran; dichloromethane; isopropyl alcohol;

Reference yield:

: 149310-67-8
ethyl (E)-5-((tetrahydro-2H-pyran-2-yl)oxy)pent-2-enoate

: 173656-68-3
(3Z,10E,12E)-3-methyl-14-tert-butyldiphenylsiloxy-7,7-bis(methoxycarbonyl)-1-tetrahydropyranyloxy-tetradeca-3,10,12-triene

Guidance literature:: Multi-step reaction with 9 steps

1: 97 percent / (i-Bu)2AlH / CH₂Cl₂; diethyl ether / 1 h / -78 °C

2: 63 percent / PCC, 3 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 1.) NaH / 1.) THF, 0 deg C, 10 min, 2.) THF, -78 deg C, 0.5 h then 15 min and to room t., 1 h

4: 86 percent / (i-Bu)2AlH / toluene; diethyl ether / 1 h / -78 °C

5: imidazole / tetrahydrofuran / 1 h / Ambient temperature

6: pyridinium-p-toluenesulfonate / propan-2-ol / 1 h / Heating

7: 100 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

8: 1.) NaH, 2.) KI / 1.) DMF, room t., 2.) DMF, THF, 70-75 deg C, 15 h

9: 1.) NaH, 2.) KI / 1.) DMF, 1 h, 35-40 deg C, 2.) DMF, THF, 70 deg C, 12 h

With 1H-imidazole; 3 A molecular sieve; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; triethylamine; pyridinium chlorochromate; potassium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; isopropyl alcohol; toluene;