(2Z,4E,6R,7S,9R,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-ol

Base Information

Chemical Name:(2Z,4E,6R,7S,9R,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-ol
CAS No.:945403-12-3
Molecular Formula:C₆₃H₁₁₆O₇Si₄
Molecular Weight:1097.95
Hs Code.:

(2Z,4E,6R,7S,9R,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-ol

Synonyms:(2Z,4E,6R,7S,9R,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-ol

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Chemical Property of (2Z,4E,6R,7S,9R,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-ol

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Technology Process of (2Z,4E,6R,7S,9R,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-ol

There total 33 articles about (2Z,4E,6R,7S,9R,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-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: 60.0%

: 945402-41-5
C₆₉H₁₃₀O₇Si₅

: 945403-12-3
(2Z,4E,6R,7S,9R,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-ol

Guidance literature:: With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 0 ℃; for 14h;
DOI:10.1021/jm061385k

Reference yield:

: 219606-81-2
(3R,4S)-4,6-bis(tert-butyldimethylsilyloxy)-3-methylhex-1-ene

: 945403-12-3
(2Z,4E,6R,7S,9R,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 91 percent / Grubbs second generation catalyst / CH₂Cl₂ / 15 h

2.1: 18-crown-6; potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1.2 h / -78 - -45 °C

2.2: 100 percent / tetrahydrofuran; toluene / 6 h / -78 - 20 °C

3.1: 92 percent / HF*pyridine / tetrahydrofuran / 0 - 20 °C

4.1: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 1.03 h / 0 °C

5.1: NaH₂PO₄*H₂O; 2-methyl-2-butene; NaClO₂ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 2.25 h / 0 - 20 °C

6.1: 0.36 g / triethylamine; DCC / CH₂Cl₂ / 0 - 20 °C

7.1: DIBALH / tetrahydrofuran; hexane / 1 h / -78 - 20 °C

8.1: 0.38 g / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

9.1: tert-butyllithium / diethyl ether; pentane / 0.33 h / -78 °C

9.2: 43 percent / diethyl ether; pentane / 1.17 h / -78 - -10 °C

10.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

11.1: 60 percent / HF*pyridine; pyridine / tetrahydrofuran / 14 h / 0 °C

With pyridine; 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; 18-crown-6 ether; pyridine-SO₃ complex; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; dicyclohexyl-carbodiimide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol; pentane; 1.1: Grubbs-II cross-metathesis / 2.2: Still-Gennari olefination;
DOI:10.1021/jm061385k

Reference yield:

: 945402-09-5
(2S,3S,4S,5R)-1-(4-methoxybenzyloxy)-8-(tert-butyldimethylsilyloxy)-2,4-dimethyloctane-3,5-diol

: 945403-12-3
(2Z,4E,6R,7S,9R,10Z,12S,13R,14S,15Z,19R,20R,21S,22S,23Z)-21-(4-methoxybenzyloxy)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-6,12,14,20,22-pentamethylhexacosa-2,4,10,15,23,25-hexaen-9-ol

Guidance literature:: Multi-step reaction with 13 steps

1.1: 60 percent / DDQ; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 0 - 20 °C

2.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

3.1: 41 percent / DIBALH / CH₂Cl₂; hexane / 12.5 h / -78 - -45 °C

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

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

6.1: 1.85 g / NaH / tetrahydrofuran / 1.3 h / 0 - 20 °C

7.1: 75 percent / HF*pyridine; pyridine / tetrahydrofuran / 6 h / 0 - 20 °C

8.1: 93 percent / triphenylphosphine; imidazole; I₂ / benzene; diethyl ether / 0.67 h / 20 °C

9.1: 78 percent / triphenylphosphine / benzene / 16 h / 20 - 80 °C

10.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C

10.2: 82 percent / tetrahydrofuran / -78 - 20 °C

11.1: tert-butyllithium / diethyl ether; pentane / 0.33 h / -78 °C

11.2: 43 percent / diethyl ether; pentane / 1.17 h / -78 - -10 °C

12.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

13.1: 60 percent / HF*pyridine; pyridine / tetrahydrofuran / 14 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; pyridine-SO₃ complex; 4 A molecular sieve; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; pentane; benzene; 5.1: Nozaki-Hiyama-Kishi reaction / 6.1: Peterson elimination;
DOI:10.1021/jm061385k