(3R,3aS,6R,7S,7aS)-3,6-dimethyl-7a-formyl-7-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-hexahydrobenzo[1,2-b]furan-2(3H)-one

Base Information

Chemical Name:(3R,3aS,6R,7S,7aS)-3,6-dimethyl-7a-formyl-7-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-hexahydrobenzo[1,2-b]furan-2(3H)-one
CAS No.:111399-02-1
Molecular Formula:C₁₇H₂₆O₅
Molecular Weight:310.39
Hs Code.:

Synonyms:(3R,3aS,6R,7S,7aS)-3,6-dimethyl-7a-formyl-7-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-hexahydrobenzo[1,2-b]furan-2(3H)-one

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Chemical Property of (3R,3aS,6R,7S,7aS)-3,6-dimethyl-7a-formyl-7-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-hexahydrobenzo[1,2-b]furan-2(3H)-one

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Technology Process of (3R,3aS,6R,7S,7aS)-3,6-dimethyl-7a-formyl-7-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-hexahydrobenzo[1,2-b]furan-2(3H)-one

There total 1 articles about (3R,3aS,6R,7S,7aS)-3,6-dimethyl-7a-formyl-7-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-hexahydrobenzo[1,2-b]furan-2(3H)-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:

: 50906-56-4
(1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.0^1,5.0^12,14]tetradecan-3-one

: 111399-02-1
(3R,3aS,6R,7S,7aS)-3,6-dimethyl-7a-formyl-7-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-hexahydrobenzo[1,2-b]furan-2(3H)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 57 percent / hydrogen / tris(triphenylphosphine)rhodium(I) chloride / benzene; ethanol

2.1: 59 percent / WCl₆; n-BuLi / tetrahydrofuran / 1.75 h / 20 °C

3.1: ozone / CH₂Cl₂; methanol / -78 - 20 °C

3.2: 93 percent / dimethyl sulfide / CH₂Cl₂; methanol / 3 h / 20 °C

4.1: 96 percent / trimethylsilyl triflate / CH₂Cl₂ / 16 h / -78 °C

With n-butyllithium; trimethylsilyl trifluoromethanesulfonate; hydrogen; tungsten(VI) chloride; ozone; Wilkinson's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; benzene; 1.1: Hydrogenation / 2.1: deoxygenation / 3.1: ozonolysis / 3.2: Reduction / 4.1: ketalization;
DOI:10.1016/S0040-4020(97)10286-1

Reference yield: 82.0%

: 107-30-2
chloromethyl methyl ether

: 111399-02-1
(3R,3aS,6R,7S,7aS)-3,6-dimethyl-7a-formyl-7-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-hexahydrobenzo[1,2-b]furan-2(3H)-one

: 141039-67-0
2-(2-(3-((2R)-methoxymethylcarbonylpropyl)-2-methoxymethyloxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane

Guidance literature:: (3R,3aS,6R,7S,7aS)-3,6-dimethyl-7a-formyl-7-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-hexahydrobenzo[1,2-b]furan-2(3H)-one; With sodium naphthalenide; In tetrahydrofuran; at -25 ℃;

chloromethyl methyl ether; With triethylamine; In tetrahydrofuran; at -25 - 20 ℃; for 4h;
DOI:10.1016/S0040-4020(97)10286-1

Reference yield: 46.0%

: 111399-02-1
(3R,3aS,6R,7S,7aS)-3,6-dimethyl-7a-formyl-7-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-hexahydrobenzo[1,2-b]furan-2(3H)-one

: 74-88-4
methyl iodide

: 141039-65-8
2-(2-(3-((2R)-methoxycarbonylpropyl)-2-methoxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane

Guidance literature:: (3R,3aS,6R,7S,7aS)-3,6-dimethyl-7a-formyl-7-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-hexahydrobenzo[1,2-b]furan-2(3H)-one; With sodium naphthalenide; In tetrahydrofuran; at -25 ℃;

methyl iodide; In tetrahydrofuran; at -25 - 20 ℃; for 16h;
DOI:10.1016/S0040-4020(97)10286-1