(3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol

Base Information

Chemical Name:(3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol
CAS No.:373645-65-9
Molecular Formula:C₄₄H₇₀O₇Si
Molecular Weight:739.121
Hs Code.:

(3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol

Synonyms:(3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol

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Chemical Property of (3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol

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Technology Process of (3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol

There total 46 articles about (3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-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: 94.0%

: 827603-09-8
(4-methoxy-2,6-dimethylphenyl) (2S,3S,4S,5S,6S,7Z)-2-[(2Z,4S,5R,6S)-5-(t-butyldimethylsilyloxy)-7-(p-methoxybenzyloxy)-2,4,6-trimethylhept-2-enyl]-3-hydroxy-5-(p-methoxybenzyloxy)-4,6-dimethyldeca-7,9-dienoate

: 373645-65-9
(3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - -15 ℃; for 5h;
DOI:10.1021/jo048534w

Reference yield: 88.0%

: 261968-21-2
(2,6-dimethylphenyl) (2S,3S,4S,5S,6S,7Z)-2-[(2Z,4S,5R,6S)-5-(t-butyldimethylsilyloxy)-7-(p-methoxybenzyloxy)-2,4,6-trimethyl-hept-2-enyl]-3-hydroxy-5-(p-methoxybenzyloxy)-4,6-dimethyldeca-7,9-dienoate

: 373645-65-9
(3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - -10 ℃;
DOI:10.1021/ja011211m

Reference yield:

: 261968-12-1
1-(p-methoxybenzyloxy)-5-hydroxy-2,4,6-trimethyl-6-hepten-3-one

: 373645-65-9
(3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 96 percent / SmI₂ / tetrahydrofuran / 1.5 h / -10 °C

2.1: 97 percent / K₂CO₃ / methanol; H₂O / 5 h / 20 °C

3.1: 94 percent / PPTS / toluene / 4 h / Heating

4.1: NaIO₄; NaHCO₃ / methanol; H₂O / 2 h / 20 °C

5.1: 82 percent / DBU; 1-(t-butyldimethylsiloxy)-1-methoxyethene / various solvent(s) / 8 h / Heating

6.1: 85 percent / methanol / 0 - 20 °C

7.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

8.1: 91 percent / aq. KOH / methanol / 1 h / Heating

9.1: 86 percent / DCC; 4-DMAP / CH₂Cl₂ / 16 h / 20 °C

10.1: LiTMP; LiBr / tetrahydrofuran / -100 °C

10.2: 81 percent / tetrahydrofuran / 0.08 h / -100 °C

11.1: 88 percent / LiAlH₄ / tetrahydrofuran / -78 - -10 °C

With 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium periodate; lithium aluminium tetrahydride; samarium diiodide; 2,2,6,6-tetramethylpiperidinyl-lithium; ketene t-butyldimethylsilyl methyl acetal; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; lithium bromide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1.1: Evans-Tischenko reaction / 5.1: Claisen rearrangement;
DOI:10.1021/ja011211m