(R,2Z,4E)-methyl 6-((4S,6S)-6-{(1Z,3R,4S,5S,7S,10R,11S,12S,13S,14Z)-4,10-dihydroxy-12-[(4-methoxybenzyl)oxy]-3,5,7,11,13-pentamethylheptadeca-1,14,16-trien-1-yl}-2,2-dimethyl-1,3-dioxan-4-yl)hepta-2,4-dienoate

Base Information

• Chemical Name: (R,2Z,4E)-methyl 6-((4S,6S)-6-{(1Z,3R,4S,5S,7S,10R,11S,12S,13S,14Z)-4,10-dihydroxy-12-[(4-methoxybenzyl)oxy]-3,5,7,11,13-pentamethylheptadeca-1,14,16-trien-1-yl}-2,2-dimethyl-1,3-dioxan-4-yl)hepta-2,4-dienoate
• CAS No.: 1309460-61-4
• Molecular Formula: C₄₄H₆₈O₈
• Molecular Weight: 725.019
• Mol file: 1309460-61-4.mol

Synonyms:(R,2Z,4E)-methyl 6-((4S,6S)-6-{(1Z,3R,4S,5S,7S,10R,11S,12S,13S,14Z)-4,10-dihydroxy-12-[(4-methoxybenzyl)oxy]-3,5,7,11,13-pentamethylheptadeca-1,14,16-trien-1-yl}-2,2-dimethyl-1,3-dioxan-4-yl)hepta-2,4-dienoate

Chemical Property of (R,2Z,4E)-methyl 6-((4S,6S)-6-{(1Z,3R,4S,5S,7S,10R,11S,12S,13S,14Z)-4,10-dihydroxy-12-[(4-methoxybenzyl)oxy]-3,5,7,11,13-pentamethylheptadeca-1,14,16-trien-1-yl}-2,2-dimethyl-1,3-dioxan-4-yl)hepta-2,4-dienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,2Z,4E)-methyl 6-((4S,6S)-6-{(1Z,3R,4S,5S,7S,10R,11S,12S,13S,14Z)-4,10-dihydroxy-12-[(4-methoxybenzyl)oxy]-3,5,7,11,13-pentamethylheptadeca-1,14,16-trien-1-yl}-2,2-dimethyl-1,3-dioxan-4-yl)hepta-2,4-dienoate

There total 21 articles about (R,2Z,4E)-methyl 6-((4S,6S)-6-{(1Z,3R,4S,5S,7S,10R,11S,12S,13S,14Z)-4,10-dihydroxy-12-[(4-methoxybenzyl)oxy]-3,5,7,11,13-pentamethylheptadeca-1,14,16-trien-1-yl}-2,2-dimethyl-1,3-dioxan-4-yl)hepta-2,4-dienoate 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: 100.0%

methyl (2Z,4E,6R,7S,9S,10Z,12R,13S,14S,16S,19R,20R,21S,22S,23Z)-7,9,13,19-tetrahydroxy-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate (1309460-60-3) + 2,2-dimethoxy-propane (77-76-9) → (R,2Z,4E)-methyl 6-((4S,6S)-6-{(1Z,3R,4S,5S,7S,10R,11S,12S,13S,14Z)-4,10-dihydroxy-12-[(4-methoxybenzyl)oxy]-3,5,7,11,13-pentamethylheptadeca-1,14,16-trien-1-yl}-2,2-dimethyl-1,3-dioxan-4-yl)hepta-2,4-dienoate (1309460-61-4)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/ejoc.201100244

Reference yield:

1-((2R,4S)-5-benzyloxy-2,4-dimethylpentyloxymethyl)-4-methoxybenzene → (R,2Z,4E)-methyl 6-((4S,6S)-6-{(1Z,3R,4S,5S,7S,10R,11S,12S,13S,14Z)-4,10-dihydroxy-12-[(4-methoxybenzyl)oxy]-3,5,7,11,13-pentamethylheptadeca-1,14,16-trien-1-yl}-2,2-dimethyl-1,3-dioxan-4-yl)hepta-2,4-dienoate (1309460-61-4)

Guidance literature:

Multi-step reaction with 21 steps

1.1: ammonium cerium (IV) nitrate; water / acetonitrile / 0 °C / Inert atmosphere

2.1: pyridine; Dess-Martin periodane / dichloromethane / Inert atmosphere

3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C / Inert atmosphere

4.2: 1.08 h / -78 - 0 °C / Inert atmosphere

5.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II) / isopropyl alcohol / 5 h / 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere

7.1: Wilkinson's catalyst; hydrogen / benzene / 3000.3 Torr

8.1: 2,6-dimethylpyridine / dichloromethane / Inert atmosphere

9.1: hydrogen / ethanol

10.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / Inert atmosphere

11.1: diethylzinc; palladium diacetate; triphenylphosphine / tetrahydrofuran; hexane / -78 - -20 °C / Inert atmosphere

12.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

13.1: n-butyllithium / hexane / 1 h / -50 °C / Inert atmosphere

13.2: 1 h / -50 - 20 °C / Inert atmosphere

14.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 24 h / 20 °C / Inert atmosphere

15.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

16.1: pyridine; Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

17.1: chromium dichloride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

18.1: potassium hydroxide / methanol; water / 0 - 20 °C / Inert atmosphere

19.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere

19.2: 0.25 h / -78 °C / Inert atmosphere

19.3: 1 h / -78 °C / Inert atmosphere

20.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

21.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; chromium dichloride; Wilkinson's catalyst; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); n-butyllithium; ammonium cerium (IV) nitrate; tetrapropylammonium perruthennate; 2-nitrobenzenesulfonyl hydrazide; water; hydrogen; tert.-butyl lithium; diethylzinc; palladium diacetate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; triphenylphosphine; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; isopropyl alcohol; acetonitrile; pentane; benzene; 2.1: Dess-Martin oxidation / 3.1: Shioiri alkynylation / 3.2: Shioiri alkynylation / 11.1: Marshall-Tamaru addition / 16.1: Dess-Martin oxidation / 17.1: Nozaki-Hiyama-Kishi coupling / 18.1: Peterson olefination;

DOI:10.1002/ejoc.201100244

Reference yield:

(2R,4S)-5-benzyloxy-2,4-dimethylpentanal → (R,2Z,4E)-methyl 6-((4S,6S)-6-{(1Z,3R,4S,5S,7S,10R,11S,12S,13S,14Z)-4,10-dihydroxy-12-[(4-methoxybenzyl)oxy]-3,5,7,11,13-pentamethylheptadeca-1,14,16-trien-1-yl}-2,2-dimethyl-1,3-dioxan-4-yl)hepta-2,4-dienoate (1309460-61-4)

Guidance literature:

Multi-step reaction with 19 steps

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C / Inert atmosphere

2.2: 1.08 h / -78 - 0 °C / Inert atmosphere

3.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II) / isopropyl alcohol / 5 h / 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere

5.1: Wilkinson's catalyst; hydrogen / benzene / 3000.3 Torr

6.1: 2,6-dimethylpyridine / dichloromethane / Inert atmosphere

7.1: hydrogen / ethanol

8.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / Inert atmosphere

9.1: diethylzinc; palladium diacetate; triphenylphosphine / tetrahydrofuran; hexane / -78 - -20 °C / Inert atmosphere

10.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

11.1: n-butyllithium / hexane / 1 h / -50 °C / Inert atmosphere

11.2: 1 h / -50 - 20 °C / Inert atmosphere

12.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 24 h / 20 °C / Inert atmosphere

13.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

14.1: pyridine; Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

15.1: chromium dichloride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

16.1: potassium hydroxide / methanol; water / 0 - 20 °C / Inert atmosphere

17.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere

17.2: 0.25 h / -78 °C / Inert atmosphere

17.3: 1 h / -78 °C / Inert atmosphere

18.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

19.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; chromium dichloride; Wilkinson's catalyst; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); n-butyllithium; tetrapropylammonium perruthennate; 2-nitrobenzenesulfonyl hydrazide; hydrogen; tert.-butyl lithium; diethylzinc; palladium diacetate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; triphenylphosphine; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; isopropyl alcohol; pentane; benzene; 1.1: Shioiri alkynylation / 1.2: Shioiri alkynylation / 9.1: Marshall-Tamaru addition / 14.1: Dess-Martin oxidation / 15.1: Nozaki-Hiyama-Kishi coupling / 16.1: Peterson olefination;

DOI:10.1002/ejoc.201100244

upstream raw materials:

({[(2S,4R)-2,4-dimethylhex-5-yn-1-yl]oxy}methyl)benzene

(2S,4S,7R,8R,9S,10S)-7,11-bis(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,8,10-tetramethylundecanal

(2R,6R,8S)-9-(benzyloxy)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8-dimethylnon-4-yn-3-one

(5S,6S,8S,11R,12R,13S,14S)-5-[(R)-but-3-yn-2-yl]-11-[(tert-butyldimethylsilanyl)oxy]-13-[(4-methoxybenzyl)oxy]-2,2,3,3,6,8,12,14,17,17,18,18-dodecamethyl-4,16-dioxa-3,17-disilanonadecane