(4R,5R,6S,7S,Z)-6-(4-methoxybenzyloxy)-4-(tert-butyldimethylsilyloxy)-5,7-dimethylundeca-8,10-dien-1-ol

Base Information

Chemical Name:(4R,5R,6S,7S,Z)-6-(4-methoxybenzyloxy)-4-(tert-butyldimethylsilyloxy)-5,7-dimethylundeca-8,10-dien-1-ol
CAS No.:623926-61-4
Molecular Formula:C₂₇H₄₆O₄Si
Molecular Weight:462.745
Hs Code.:

Synonyms:(4R,5R,6S,7S,Z)-6-(4-methoxybenzyloxy)-4-(tert-butyldimethylsilyloxy)-5,7-dimethylundeca-8,10-dien-1-ol

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Chemical Property of (4R,5R,6S,7S,Z)-6-(4-methoxybenzyloxy)-4-(tert-butyldimethylsilyloxy)-5,7-dimethylundeca-8,10-dien-1-ol

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Technology Process of (4R,5R,6S,7S,Z)-6-(4-methoxybenzyloxy)-4-(tert-butyldimethylsilyloxy)-5,7-dimethylundeca-8,10-dien-1-ol

There total 13 articles about (4R,5R,6S,7S,Z)-6-(4-methoxybenzyloxy)-4-(tert-butyldimethylsilyloxy)-5,7-dimethylundeca-8,10-dien-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: 83.0%

: 623926-60-3
1-(((5S,6S,7R,8R,Z)-8,11-bis(tert-butyldimethylsilyloxy)-5,7-dimethylundeca-1,3-dien-6-yloxy)methyl)-4-methoxybenzene

: 623926-61-4
(4R,5R,6S,7S,Z)-6-(4-methoxybenzyloxy)-4-(tert-butyldimethylsilyloxy)-5,7-dimethylundeca-8,10-dien-1-ol

Guidance literature:: With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1016/S0968-0896(03)00186-X

Reference yield:

: 1026307-82-3
(2R,3R,4R,5R)-5,8-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octanal

: 623926-61-4
(4R,5R,6S,7S,Z)-6-(4-methoxybenzyloxy)-4-(tert-butyldimethylsilyloxy)-5,7-dimethylundeca-8,10-dien-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: CrCl₂ / tetrahydrofuran / 17 h / 20 °C

2: 1.85 g / NaH / tetrahydrofuran / 1.3 h / 0 - 20 °C

3: 75 percent / HF*pyridine; pyridine / tetrahydrofuran / 6 h / 0 - 20 °C

With pyridine; chromium dichloride; sodium hydride; pyridine hydrogenfluoride; In tetrahydrofuran; 1: Nozaki-Hiyama-Kishi reaction / 2: Peterson elimination;
DOI:10.1021/jm061385k

Reference yield:

: 945402-33-5
(5R,6S,7S)-8-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilyloxy)-6-hydroxy-5,7-dimethyloctan-4-one

: 623926-61-4
(4R,5R,6S,7S,Z)-6-(4-methoxybenzyloxy)-4-(tert-butyldimethylsilyloxy)-5,7-dimethylundeca-8,10-dien-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: Et₂BOMe / tetrahydrofuran; methanol / 0.67 h / -78 °C

1.2: 85 percent / NaBH₄ / tetrahydrofuran; methanol / 7.17 h / -78 °C

2.1: 60 percent / DDQ; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 0 - 20 °C

3.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

4.1: 41 percent / DIBALH / CH₂Cl₂; hexane / 12.5 h / -78 - -45 °C

5.1: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 1.17 h / 0 °C

6.1: CrCl₂ / tetrahydrofuran / 17 h / 20 °C

7.1: 1.85 g / NaH / tetrahydrofuran / 1.3 h / 0 - 20 °C

8.1: 75 percent / HF*pyridine; pyridine / tetrahydrofuran / 6 h / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; chromium dichloride; pyridine-SO₃ complex; 4 A molecular sieve; diethyl methoxy borane; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; 6.1: Nozaki-Hiyama-Kishi reaction / 7.1: Peterson elimination;
DOI:10.1021/jm061385k