(1S,7R,7aS)-7-Acetoxy-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1-((R)-2-methoxycarbonyl-1-methyl-ethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester

Base Information

Chemical Name:(1S,7R,7aS)-7-Acetoxy-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1-((R)-2-methoxycarbonyl-1-methyl-ethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester
CAS No.:131010-96-3
Molecular Formula:C₂₉H₄₀O₈
Molecular Weight:516.632
Hs Code.:

(1S,7R,7aS)-7-Acetoxy-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1-((R)-2-methoxycarbonyl-1-methyl-ethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester

Synonyms:(1S,7R,7aS)-7-Acetoxy-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1-((R)-2-methoxycarbonyl-1-methyl-ethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester

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Chemical Property of (1S,7R,7aS)-7-Acetoxy-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1-((R)-2-methoxycarbonyl-1-methyl-ethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester

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Technology Process of (1S,7R,7aS)-7-Acetoxy-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1-((R)-2-methoxycarbonyl-1-methyl-ethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester

There total 1 articles about (1S,7R,7aS)-7-Acetoxy-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1-((R)-2-methoxycarbonyl-1-methyl-ethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl 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:

: 562-13-0
2,2-dimethyl-1,3-cyclohexanedione

: 131010-96-3
(1S,7R,7aS)-7-Acetoxy-5-((1S,4S)-3,3-dimethyl-2-oxo-7-oxa-bicyclo[2.2.1]hept-1-ylmethyl)-1-((R)-2-methoxycarbonyl-1-methyl-ethyl)-1,7a-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 16 steps

1: catechol borane, oxazaborolidine / toluene / -78 °C

2: imidazole / dimethylformamide / 23 °C

3: NaH, THF

4: 1.) NaH / 1.) THF, 23 deg C, 2.) -40 deg C

5: 66 percent / Pd(OAc)2, PPh₃ / tetrahydrofuran / 0.25 h / 70 °C

6: NaHB(OMe)3 / tetrahydrofuran / 8 h / -20 °C

7: pyridine / CH₂Cl₂ / 0.5 h / 23 °C

8: Cl₃CCOOH / tetrahydrofuran; H₂O / 5 h / 23 °C

9: 1.) a) mercuric trifluoroacetate, HgO, b) Et₄NCl, 2.) Bu₂SnH₂ / 1.) a) CH₃CN, 23 deg C, 24 h, 2.) toluene, from -78 deg C to 0 deg C

10: K₂CO₃-methanol / methanol / 0.17 h / 23 °C

11: pyridinium dichromate / dimethylformamide / 0.5 h / 23 °C

12: 83 percent / FeCl₃ / CH₂Cl₂ / 12 h / -78 °C

13: HF, pyridine / acetonitrile / 0.75 h / 23 °C

14: pyridinium chlorochromate, Al₂O₃ / CH₂Cl₂ / 12 h / 23 °C

15: aq. sodium chlorite, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.5 h / 23 °C

With tetrahydrofuran; pyridine; 1H-imidazole; methanol; aluminum oxide; palladium diacetate; sodium chlorite; sodium dihydrogenphosphate; dipyridinium dichromate; (S)-oxazaborolidine; 2-methyl-but-2-ene; hydrogen fluoride; tetraethylammonium chloride; mercury(II) trifluoroacetate; sodium trimethoxyborohydride; iron(III) chloride; sodium hydride; dibutyltin; potassium carbonate; triphenylphosphine; pyridinium chlorochromate; mercury(II) oxide; trichloroacetic acid; benzo[1,3,2]dioxaborole; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja00180a064