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

Base Information

• Chemical Name: 2-(2-(3-((2R)-methoxymethylcarbonylpropyl)-2-methoxymethyloxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane
• CAS No.: 141039-67-0
• Molecular Formula: C₂₁H₃₆O₇
• Molecular Weight: 400.513
• Mol file: 141039-67-0.mol

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

Chemical Property of 2-(2-(3-((2R)-methoxymethylcarbonylpropyl)-2-methoxymethyloxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2-(3-((2R)-methoxymethylcarbonylpropyl)-2-methoxymethyloxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane

There total 7 articles about 2-(2-(3-((2R)-methoxymethylcarbonylpropyl)-2-methoxymethyloxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane 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: 82.0%

chloromethyl methyl ether (107-30-2) + (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 (111399-02-1) → 2-(2-(3-((2R)-methoxymethylcarbonylpropyl)-2-methoxymethyloxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane (141039-67-0)

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:

(1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.01,5.012,14]tetradecan-3-one (50906-56-4) → 2-(2-(3-((2R)-methoxymethylcarbonylpropyl)-2-methoxymethyloxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane (141039-67-0)

Guidance literature:

Multi-step reaction with 5 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

5.1: sodium naphthalenide / tetrahydrofuran / -25 °C

5.2: 82 percent / triethylamine / tetrahydrofuran / 4 h / -25 - 20 °C

With n-butyllithium; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium naphthalenide; 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 / 5.1: Reduction / 5.2: Alkylation;

DOI:10.1016/S0040-4020(97)10286-1

Reference yield:

(3R,3a,6R,6aS,10aS)-3a,4,5,6,6a,7,8,8a-octahydro-3,6,9-trimethylnaphtho[8a,1-b]furan-2(3H)-one (104196-16-9) → 2-(2-(3-((2R)-methoxymethylcarbonylpropyl)-2-methoxymethyloxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane (141039-67-0)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 93 percent / dimethyl sulfide / CH₂Cl₂; methanol / 3 h / 20 °C

2.1: 96 percent / trimethylsilyl triflate / CH₂Cl₂ / 16 h / -78 °C

3.1: sodium naphthalenide / tetrahydrofuran / -25 °C

3.2: 82 percent / triethylamine / tetrahydrofuran / 4 h / -25 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; sodium naphthalenide; ozone; In tetrahydrofuran; methanol; dichloromethane; 1.1: ozonolysis / 1.2: Reduction / 2.1: ketalization / 3.1: Reduction / 3.2: Alkylation;

DOI:10.1016/S0040-4020(97)10286-1

upstream raw materials:

chloromethyl methyl ether

(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

(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

(3R,3a,6R,6aS,10aS)-3a,4,5,6,6a,7,8,8a-octahydro-3,6,9-trimethylnaphtho[8a,1-b]furan-2(3H)-one

Downstream raw materials:

2-(2-(3-(3-hydroxy-(2R)-methylpropyl)-2-methoxymethoxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane

C₁₂H₁₃O₂(CH₃)3(O)(OO)

(+)-deoxyartemisinin

(+)-artemisinin