Acetic acid 6-[1-((1aR,3aS,5S,7aS,7bS)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-meth-(Z)-ylidene]-4-hydroxy-5-methyl-3-oxo-cyclohexa-1,4-dienyl ester

Base Information

Chemical Name:Acetic acid 6-[1-((1aR,3aS,5S,7aS,7bS)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-meth-(Z)-ylidene]-4-hydroxy-5-methyl-3-oxo-cyclohexa-1,4-dienyl ester
CAS No.:393803-69-5
Molecular Formula:C₂₆H₃₄O₇
Molecular Weight:458.552
Hs Code.:

Acetic acid 6-[1-((1aR,3aS,5S,7aS,7bS)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-meth-(Z)-ylidene]-4-hydroxy-5-methyl-3-oxo-cyclohexa-1,4-dienyl ester

Synonyms:Acetic acid 6-[1-((1aR,3aS,5S,7aS,7bS)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-meth-(Z)-ylidene]-4-hydroxy-5-methyl-3-oxo-cyclohexa-1,4-dienyl ester

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Chemical Property of Acetic acid 6-[1-((1aR,3aS,5S,7aS,7bS)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-meth-(Z)-ylidene]-4-hydroxy-5-methyl-3-oxo-cyclohexa-1,4-dienyl ester

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Technology Process of Acetic acid 6-[1-((1aR,3aS,5S,7aS,7bS)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-meth-(Z)-ylidene]-4-hydroxy-5-methyl-3-oxo-cyclohexa-1,4-dienyl ester

There total 19 articles about Acetic acid 6-[1-((1aR,3aS,5S,7aS,7bS)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-meth-(Z)-ylidene]-4-hydroxy-5-methyl-3-oxo-cyclohexa-1,4-dienyl ester 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: 51.0%

: 393803-68-4
Acetic acid (S)-(6-acetoxy-3,4-dihydroxy-2-methyl-phenyl)-((1aR,3aS,5S,7aS,7bR)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-methyl ester

: 393803-69-5
Acetic acid 6-[1-((1aR,3aS,5S,7aS,7bS)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-meth-(Z)-ylidene]-4-hydroxy-5-methyl-3-oxo-cyclohexa-1,4-dienyl ester

: UPA₀₀₄₄

Guidance literature:: With sodium hydrogencarbonate; In methanol; for 1h;
DOI:10.1021/ol016960n

Reference yield:

: 114626-74-3
(1aR,3aS,5S,7aS,7bS)-5-Acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalene-7b-carboxylic acid methyl ester

: 393803-69-5
Acetic acid 6-[1-((1aR,3aS,5S,7aS,7bS)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-meth-(Z)-ylidene]-4-hydroxy-5-methyl-3-oxo-cyclohexa-1,4-dienyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 286 mg / NaOMe / methanol / 22 h / 20 °C

2.1: 86 percent / pyridine / 1 h / 0 °C

3.1: 70 percent / Dibal-H / toluene / 0.5 h / -78 °C

4.1: t-BuLi / diethyl ether; pentane / 1 h / -78 °C

4.2: 15 percent / diethyl ether; pentane / 0.5 h / -78 °C

5.1: 90 percent / DMAP; pyridine / 20 °C

6.1: 87 percent / aq. HF / acetonitrile / 0 °C

7.1: 94 percent / pyridine / 20 °C

8.1: 93 percent / H₂ / Pd/C / methanol / 20 °C / atmospheric pressure

9.1: 10 percent / NaHCO₃ / methanol / 4 h / 0 °C

With pyridine; dmap; hydrogen fluoride; hydrogen; tert.-butyl lithium; sodium methylate; diisobutylaluminium hydride; sodium hydrogencarbonate; palladium on activated charcoal; In methanol; diethyl ether; toluene; acetonitrile; pentane;
DOI:10.1021/ol016960n

Reference yield:

: 393803-37-7
(1aR,3aS,5S,7aS,7bS)-5-(tert-Butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalene-7b-carboxylic acid methyl ester

: 393803-69-5
Acetic acid 6-[1-((1aR,3aS,5S,7aS,7bS)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-meth-(Z)-ylidene]-4-hydroxy-5-methyl-3-oxo-cyclohexa-1,4-dienyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 70 percent / Dibal-H / toluene / 0.5 h / -78 °C

2.1: t-BuLi / diethyl ether; pentane / 1 h / -78 °C

2.2: 15 percent / diethyl ether; pentane / 0.5 h / -78 °C

3.1: 90 percent / DMAP; pyridine / 20 °C

4.1: 87 percent / aq. HF / acetonitrile / 0 °C

5.1: 94 percent / pyridine / 20 °C

6.1: 93 percent / H₂ / Pd/C / methanol / 20 °C / atmospheric pressure

7.1: 10 percent / NaHCO₃ / methanol / 4 h / 0 °C

With pyridine; dmap; hydrogen fluoride; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; palladium on activated charcoal; In methanol; diethyl ether; toluene; acetonitrile; pentane;
DOI:10.1021/ol016960n