(2S,3E,6Z)-1-((2S,6R)-{6-(R,E)-[4-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2-methylpent-1-enyl]-4-methylenetetrahydropyran-2-yl})-8-(tert-butyldiphenylsilanyloxy)-6-methylocta-3,6-dien-2-ol

Base Information

Chemical Name:(2S,3E,6Z)-1-((2S,6R)-{6-(R,E)-[4-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2-methylpent-1-enyl]-4-methylenetetrahydropyran-2-yl})-8-(tert-butyldiphenylsilanyloxy)-6-methylocta-3,6-dien-2-ol
CAS No.:860651-97-4
Molecular Formula:C₅₁H₇₄O₆Si₂
Molecular Weight:839.316
Hs Code.:

(2S,3E,6Z)-1-((2S,6R)-{6-(R,E)-[4-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2-methylpent-1-enyl]-4-methylenetetrahydropyran-2-yl})-8-(tert-butyldiphenylsilanyloxy)-6-methylocta-3,6-dien-2-ol

Synonyms:(2S,3E,6Z)-1-((2S,6R)-{6-(R,E)-[4-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2-methylpent-1-enyl]-4-methylenetetrahydropyran-2-yl})-8-(tert-butyldiphenylsilanyloxy)-6-methylocta-3,6-dien-2-ol

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Chemical Property of (2S,3E,6Z)-1-((2S,6R)-{6-(R,E)-[4-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2-methylpent-1-enyl]-4-methylenetetrahydropyran-2-yl})-8-(tert-butyldiphenylsilanyloxy)-6-methylocta-3,6-dien-2-ol

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Technology Process of (2S,3E,6Z)-1-((2S,6R)-{6-(R,E)-[4-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2-methylpent-1-enyl]-4-methylenetetrahydropyran-2-yl})-8-(tert-butyldiphenylsilanyloxy)-6-methylocta-3,6-dien-2-ol

There total 19 articles about (2S,3E,6Z)-1-((2S,6R)-{6-(R,E)-[4-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2-methylpent-1-enyl]-4-methylenetetrahydropyran-2-yl})-8-(tert-butyldiphenylsilanyloxy)-6-methylocta-3,6-dien-2-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:

: (2S,4S,6S)-2-[(E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-pent-1-enyl]-4-[(1E,4Z)-6-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hexa-1,4-dienyl]-6-(2-trimethylsilanylmethyl-allyl)-[1,3]dioxane

: 860651-97-4
(2S,3E,6Z)-1-((2S,6R)-{6-(R,E)-[4-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2-methylpent-1-enyl]-4-methylenetetrahydropyran-2-yl})-8-(tert-butyldiphenylsilanyloxy)-6-methylocta-3,6-dien-2-ol

Guidance literature:: With pyridinium triflate; magnesium sulfate; In dichloromethane; for 1.5h;
DOI:10.1002/anie.200500564

Reference yield:

: 1-(((E)-4-(4-methoxybenzyloxy)but-2-enyloxy)methyl)-4-methoxybenzene

: 860651-97-4
(2S,3E,6Z)-1-((2S,6R)-{6-(R,E)-[4-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2-methylpent-1-enyl]-4-methylenetetrahydropyran-2-yl})-8-(tert-butyldiphenylsilanyloxy)-6-methylocta-3,6-dien-2-ol

Guidance literature:: Multi-step reaction with 8 steps

1: AD-mix-α; H2O / 2-methyl-propan-2-ol / 0 - 20 °C

2: 1.44 g / sodium periodate/SiO₂ / CH₂Cl₂ / 0.5 h

3: 6-bis[(4R)-4-phenyl-2-oxazolin-2-yl]pyridine; CuCl₂; AgSbF₆ / CH₂Cl₂ / 4 h / -78 °C

4: 89 percent / imidazole / dimethylformamide / 18 h

5: 80 percent / LiAlH₄ / diethyl ether / 1 h

6: 438 mg / TMSOTf / CH₂Cl₂ / 0.75 h / -78 °C

7: CeCl₃ / diethyl ether; tetrahydrofuran / 18 h / -78 - 20 °C

8: 239 mg / pyridinium triflate; MgSO₄ / CH₂Cl₂ / 1.5 h

With 1H-imidazole; sodium periodate; AD-mix-α; silver hexafluoroantimonate; lithium aluminium tetrahydride; cerium(III) chloride; trimethylsilyl trifluoromethanesulfonate; water; pyridinium triflate; silica gel; magnesium sulfate; 2,6-bis[(4R)-5,5-dihydro-4-phenyl-2-oxazolyl]pyridine; copper dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/anie.200500564

Reference yield:

: 860651-93-0
(2E,5Z)-7-(tert-butyldiphenylsilanyloxy)-5-methylhepta-2,5-dienal

: 860651-97-4
(2S,3E,6Z)-1-((2S,6R)-{6-(R,E)-[4-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2-methylpent-1-enyl]-4-methylenetetrahydropyran-2-yl})-8-(tert-butyldiphenylsilanyloxy)-6-methylocta-3,6-dien-2-ol

Guidance literature:: Multi-step reaction with 7 steps

1: SiCl₄; chiral Denmark's bisphosphoramide catalyst / CH₂Cl₂ / 18 h / -78 °C

2: 1 h / Heating

3: diethylmethoxyborane; NaBH₄ / tetrahydrofuran / 18 h / -78 °C

4: imidazole; 4-dimethylaminopyridine / dimethylformamide / 18 h

5: 438 mg / TMSOTf / CH₂Cl₂ / 0.75 h / -78 °C

6: CeCl₃ / diethyl ether; tetrahydrofuran / 18 h / -78 - 20 °C

7: 239 mg / pyridinium triflate; MgSO₄ / CH₂Cl₂ / 1.5 h

With 1H-imidazole; dmap; sodium tetrahydroborate; cerium(III) chloride; tetrachlorosilane; trimethylsilyl trifluoromethanesulfonate; chiral Denmark's bisphosphoramide catalyst; diethyl methoxy borane; pyridinium triflate; magnesium sulfate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200500564