(1R,2E,5R,8E,10Z,13S,14E,17R)-13-((4-methoxybenzyloxy)methoxy)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-19-methylene-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one

Base Information

• Chemical Name: (1R,2E,5R,8E,10Z,13S,14E,17R)-13-((4-methoxybenzyloxy)methoxy)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-19-methylene-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one
• CAS No.: 860652-00-2
• Molecular Formula: C₄₀H₅₀O₈
• Molecular Weight: 658.832

Synonyms:(1R,2E,5R,8E,10Z,13S,14E,17R)-13-((4-methoxybenzyloxy)methoxy)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-19-methylene-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one

Chemical Property of (1R,2E,5R,8E,10Z,13S,14E,17R)-13-((4-methoxybenzyloxy)methoxy)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-19-methylene-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one

Chemical Property:

Purity/Quality:

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Technology Process of (1R,2E,5R,8E,10Z,13S,14E,17R)-13-((4-methoxybenzyloxy)methoxy)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-19-methylene-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one

There total 24 articles about (1R,2E,5R,8E,10Z,13S,14E,17R)-13-((4-methoxybenzyloxy)methoxy)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-19-methylene-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one 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: 73.0%

(diethoxyphosphoryl)acetic acid (R)-4-((2R,6R)-{6-((2E,4S,6Z)-[4-(4-methoxybenzyloxymethoxy)-6-methyl-8-oxoocta-2,6-dienyl])-4-methylenetetrahydropyran-2-yl})-1-(4-methoxybenzyloxymethyl)-[(E)-3-methylbut-3-en]yl ester (860652-04-6) → (1R,2E,5R,8E,10Z,13S,14E,17R)-13-((4-methoxybenzyloxy)methoxy)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-19-methylene-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one (860652-00-2)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃; for 1.67h;

DOI:10.1002/anie.200500564

Reference yield:

1-(((E)-4-(4-methoxybenzyloxy)but-2-enyloxy)methyl)-4-methoxybenzene → (1R,2E,5R,8E,10Z,13S,14E,17R)-13-((4-methoxybenzyloxy)methoxy)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-19-methylene-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one (860652-00-2)

Guidance literature:

Multi-step reaction with 15 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

9: (n-Bu)3P / tetrahydrofuran / 3 h / 20 °C

10: 0.266 g / aq. H₂O₂; pyridine / CH₂Cl₂ / 1 h / -30 °C

11: 4-dimethylaminopyridine; (i-Pr)2NEt / CH₂Cl₂ / 6 h

12: 102 mg / HF*pyridine; pyridine / tetrahydrofuran / 0 - 20 °C

13: 87 percent / TEMPO; bis(acetoxy)iodobenzene / CH₂Cl₂ / 1.7 h / 20 °C

14: 95 percent / DCC; DMAP / CH₂Cl₂ / 0.25 h / 20 °C

15: 73 percent / sodium hexamethyldisilylamide / tetrahydrofuran / 1.67 h / -78 - 0 °C

With pyridine; 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium periodate; AD-mix-α; silver hexafluoroantimonate; lithium aluminium tetrahydride; cerium(III) chloride; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; [bis(acetoxy)iodo]benzene; water; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium triflate; silica gel; magnesium sulfate; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 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; 15: Horner-Emmons olefination;

DOI:10.1002/anie.200500564

Reference yield:

(2E,5Z)-7-(tert-butyldiphenylsilanyloxy)-5-methylhepta-2,5-dienal (860651-93-0) → (1R,2E,5R,8E,10Z,13S,14E,17R)-13-((4-methoxybenzyloxy)methoxy)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-19-methylene-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one (860652-00-2)

Guidance literature:

Multi-step reaction with 14 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

8: (n-Bu)3P / tetrahydrofuran / 3 h / 20 °C

9: 0.266 g / aq. H₂O₂; pyridine / CH₂Cl₂ / 1 h / -30 °C

10: 4-dimethylaminopyridine; (i-Pr)2NEt / CH₂Cl₂ / 6 h

11: 102 mg / HF*pyridine; pyridine / tetrahydrofuran / 0 - 20 °C

12: 87 percent / TEMPO; bis(acetoxy)iodobenzene / CH₂Cl₂ / 1.7 h / 20 °C

13: 95 percent / DCC; DMAP / CH₂Cl₂ / 0.25 h / 20 °C

14: 73 percent / sodium hexamethyldisilylamide / tetrahydrofuran / 1.67 h / -78 - 0 °C

With pyridine; 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; cerium(III) chloride; tetrachlorosilane; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; [bis(acetoxy)iodo]benzene; chiral Denmark's bisphosphoramide catalyst; diethyl methoxy borane; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium triflate; magnesium sulfate; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 14: Horner-Emmons olefination;

DOI:10.1002/anie.200500564

upstream raw materials:

(diethoxyphosphoryl)acetic acid (R)-4-((2R,6R)-{6-((2E,4S,6Z)-[4-(4-methoxybenzyloxymethoxy)-6-methyl-8-oxoocta-2,6-dienyl])-4-methylenetetrahydropyran-2-yl})-1-(4-methoxybenzyloxymethyl)-[(E)-3-methylbut-3-en]yl ester

(2E,5Z)-7-(tert-butyldiphenylsilanyloxy)-5-methylhepta-2,5-dienal

6-[(S,3E,6Z)-8-(tert-butyldiphenylsilanyloxy)-2-hydroxy-6-methylocta-3,6-dienyl]-2,2-dimethyl-[1,3]dioxin-4-one

(S,6E,9Z)-11-(tert-butyldiphenylsilanyloxy)-5-hydroxy-9-methyl-3-oxoundeca-6,9-dienoic acid butyl ester

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