(5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl benzoate

Base Information

• Chemical Name: (5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl benzoate
• CAS No.: 163381-14-4
• Molecular Formula: C₂₂H₂₈O₆
• Molecular Weight: 388.461

Synonyms:(5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl benzoate

Chemical Property of (5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl benzoate

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of (5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl benzoate

There total 5 articles about (5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl benzoate 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: 80.0%

dihydroartemisinin (71939-50-9) + trichloroacetonitrile (545-06-2) + benzoic acid (65-85-0,8013-63-6) → (5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl benzoate (163381-14-4)

Guidance literature:

dihydroartemisinin; trichloroacetonitrile; With 1,8-diazabicyclo-[5,4,0]-undecane; In dichloromethane; for 18h;

benzoic acid; In dichloromethane; for 2h;

DOI:10.1002/1099-0690(20021)2002:1<113::AID-EJOC113>3.0.CO;2-N

Reference yield: 53.0%

dihydroartemisinin (71939-50-9) + benzoic acid (65-85-0,8013-63-6) → (5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl benzoate (163381-14-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃;

DOI:10.1002/1099-0690(20021)2002:1<113::AID-EJOC113>3.0.CO;2-N

Reference yield: 38.0%

10α-dihydroartemisinyl benzoate (82596-25-6) → 9,10-dehydrodihydroartemisinin (82596-30-3) + (5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl benzoate (163381-14-4) + bis(3,6,9-trimethyl-3,12-epidioxy-3,4,5,5a,6,7,8,8a,9,10-decahydro-12H-pyrano[4,3-j][1,2]benzodioxepin-10-yl) ether (150358-71-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1002/ejoc.200300064

upstream raw materials:

dihydroartemisinin

trichloroacetonitrile

benzoic acid

10α-dihydroartemisinyl benzoate

Downstream raw materials:

10α-(2'-furyl)-10-deoxo-10-dihydroartemisinin

9,10-dehydrodihydroartemisinin

bis(3,6,9-trimethyl-3,12-epidioxy-3,4,5,5a,6,7,8,8a,9,10-decahydro-12H-pyrano[4,3-j][1,2]benzodioxepin-10-yl) ether

10α-(2',4'-dimethoxyphenyl)-10-deoxo-10-dihydroartemisin

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