(3S,3aR,3a¹R,6aR,7S,7aR,10S,11S,11aS,11bS)-7,11-dihydroxy-5,5,8,8-tetramethyl-15-methylene-10-(4-phenyl-1H-1,2,3-triazol-1-yl)decahydro-1H-6a,11a-(epoxymethano)-3,3a¹-ethanophenanthro[1,10-de][1,3]dioxin-14-one

Base Information

• Chemical Name: (3S,3aR,3a¹R,6aR,7S,7aR,10S,11S,11aS,11bS)-7,11-dihydroxy-5,5,8,8-tetramethyl-15-methylene-10-(4-phenyl-1H-1,2,3-triazol-1-yl)decahydro-1H-6a,11a-(epoxymethano)-3,3a¹-ethanophenanthro[1,10-de][1,3]dioxin-14-one
• CAS No.: 1446495-06-2
• Molecular Formula: C₃₁H₃₇N₃O₆
• Molecular Weight: 547.651

Synonyms:(3S,3aR,3a¹R,6aR,7S,7aR,10S,11S,11aS,11bS)-7,11-dihydroxy-5,5,8,8-tetramethyl-15-methylene-10-(4-phenyl-1H-1,2,3-triazol-1-yl)decahydro-1H-6a,11a-(epoxymethano)-3,3a¹-ethanophenanthro[1,10-de][1,3]dioxin-14-one

Chemical Property of (3S,3aR,3a¹R,6aR,7S,7aR,10S,11S,11aS,11bS)-7,11-dihydroxy-5,5,8,8-tetramethyl-15-methylene-10-(4-phenyl-1H-1,2,3-triazol-1-yl)decahydro-1H-6a,11a-(epoxymethano)-3,3a¹-ethanophenanthro[1,10-de][1,3]dioxin-14-one

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Technology Process of (3S,3aR,3a¹R,6aR,7S,7aR,10S,11S,11aS,11bS)-7,11-dihydroxy-5,5,8,8-tetramethyl-15-methylene-10-(4-phenyl-1H-1,2,3-triazol-1-yl)decahydro-1H-6a,11a-(epoxymethano)-3,3a¹-ethanophenanthro[1,10-de][1,3]dioxin-14-one

There total 5 articles about (3S,3aR,3a¹R,6aR,7S,7aR,10S,11S,11aS,11bS)-7,11-dihydroxy-5,5,8,8-tetramethyl-15-methylene-10-(4-phenyl-1H-1,2,3-triazol-1-yl)decahydro-1H-6a,11a-(epoxymethano)-3,3a¹-ethanophenanthro[1,10-de][1,3]dioxin-14-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: 60.0%

(3S,3aR,3a1R,6aR,7S,7aR,10S,11S,11aS,11bS)-10-azido-7,11-dihydroxy-5,5,8,8-tetramethyl-15-methylenedecahydro-1H-6a,11a-(epoxymethano)-3,3a1-ethanophenanthro[1,10-de][1,3]dioxin-14-one (1446495-05-1) + phenylacetylene (536-74-3) → (3S,3aR,3a1R,6aR,7S,7aR,10S,11S,11aS,11bS)-7,11-dihydroxy-5,5,8,8-tetramethyl-15-methylene-10-(4-phenyl-1H-1,2,3-triazol-1-yl)decahydro-1H-6a,11a-(epoxymethano)-3,3a1-ethanophenanthro[1,10-de][1,3]dioxin-14-one (1446495-06-2)

Guidance literature:

With copper(l) iodide; In acetonitrile; at 85 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ol4015865

Reference yield:

(3S,3aR,3a1R,6aR,7S,7aR,11S,11aS,11bS)-7-hydroxy-5,5,8,8-tetramethyl-15-methylene-14-oxodecahydro-1H-6a,11a-(epoxymethano)-3,3a1-ethanophenanthro[1,10-de][1,3]dioxin-11-yl methanesulfonate (1446494-89-8) → (3S,3aR,3a1R,6aR,7S,7aR,10S,11S,11aS,11bS)-7,11-dihydroxy-5,5,8,8-tetramethyl-15-methylene-10-(4-phenyl-1H-1,2,3-triazol-1-yl)decahydro-1H-6a,11a-(epoxymethano)-3,3a1-ethanophenanthro[1,10-de][1,3]dioxin-14-one (1446495-06-2)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium bromide; lithium carbonate / N,N-dimethyl-formamide / 2 h / 115 °C / Inert atmosphere

2: sodium azide; lithium perchlorate / water; ethanol / 24 h / 85 °C / Inert atmosphere

3: copper(l) iodide / acetonitrile / 16 h / 85 °C / Inert atmosphere

With copper(l) iodide; sodium azide; lithium perchlorate; lithium carbonate; lithium bromide; In ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ol4015865

Reference yield:

oridonin (28957-04-2,28957-10-0) → (3S,3aR,3a1R,6aR,7S,7aR,10S,11S,11aS,11bS)-7,11-dihydroxy-5,5,8,8-tetramethyl-15-methylene-10-(4-phenyl-1H-1,2,3-triazol-1-yl)decahydro-1H-6a,11a-(epoxymethano)-3,3a1-ethanophenanthro[1,10-de][1,3]dioxin-14-one (1446495-06-2)

Guidance literature:

Multi-step reaction with 5 steps

1: toluene-4-sulfonic acid / acetone / 2 h / 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

3: lithium bromide; lithium carbonate / N,N-dimethyl-formamide / 2 h / 115 °C / Inert atmosphere

4: sodium azide; lithium perchlorate / water; ethanol / 24 h / 85 °C / Inert atmosphere

5: copper(l) iodide / acetonitrile / 16 h / 85 °C / Inert atmosphere

With copper(l) iodide; sodium azide; lithium perchlorate; lithium carbonate; toluene-4-sulfonic acid; triethylamine; lithium bromide; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/ol4015865

upstream raw materials:

(3S,3aR,3a¹R,6aR,7S,7aR,10S,11S,11aS,11bS)-10-azido-7,11-dihydroxy-5,5,8,8-tetramethyl-15-methylenedecahydro-1H-6a,11a-(epoxymethano)-3,3a¹-ethanophenanthro[1,10-de][1,3]dioxin-14-one

phenylacetylene

oridonin

(3S,3aR,3a¹R,6aR,7S,7aR,11S,11aS,11bS)-7-hydroxy-5,5,8,8-tetramethyl-15-methylene-14-oxodecahydro-1H-6a,11a-(epoxymethano)-3,3a¹-ethanophenanthro[1,10-de][1,3]dioxin-11-yl methanesulfonate

Downstream raw materials:

(1S,2S,4aR,5S,6S,6aR,9S,11aS,11bS,14R)-1,5,6,14-tetrahydroxy-4,4-dimethyl-8-methylene-2-(4-phenyl-1H-1,2,3-triazol-1-yl)decahydro-1H-6,11b-(epoxymethano)-6a,9-methanocyclohepta[a]naphthalen-7(8H)-one

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