(1S,2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-1-((Z)-1-methoxy-2-(ethoxycarbonyl)ethenyl)-2,4,5-trimethylcyclohex-3-en-1-ol

Base Information

• Chemical Name: (1S,2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-1-((Z)-1-methoxy-2-(ethoxycarbonyl)ethenyl)-2,4,5-trimethylcyclohex-3-en-1-ol
• CAS No.: 1428980-17-9
• Molecular Formula: C₁₉H₃₀O₆
• Molecular Weight: 354.444

Synonyms:(1S,2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-1-((Z)-1-methoxy-2-(ethoxycarbonyl)ethenyl)-2,4,5-trimethylcyclohex-3-en-1-ol

Chemical Property of (1S,2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-1-((Z)-1-methoxy-2-(ethoxycarbonyl)ethenyl)-2,4,5-trimethylcyclohex-3-en-1-ol

Chemical Property:

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Technology Process of (1S,2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-1-((Z)-1-methoxy-2-(ethoxycarbonyl)ethenyl)-2,4,5-trimethylcyclohex-3-en-1-ol

There total 16 articles about (1S,2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-1-((Z)-1-methoxy-2-(ethoxycarbonyl)ethenyl)-2,4,5-trimethylcyclohex-3-en-1-ol 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: 28.0%

(1S,2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-1(2-(ethoxycarbonyl)ethynyl)-2,4,5-trimethylcyclohex-3-en-1-ol (1428980-14-6) → (5S,6R,9R)-6-((1,3-dioxolan-2-yl)methyl)-4-methoxy-6,8,9-trimethyl-1-oxaspiro[4.5]deca-3,7-dien-2-one (1428980-16-8) + (1S,2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-1-((Z)-1-methoxy-2-(ethoxycarbonyl)ethenyl)-2,4,5-trimethylcyclohex-3-en-1-ol (1428980-17-9)

Guidance literature:

With sodium methylate; In methanol; at 20 - 60 ℃; for 34.5h; Inert atmosphere; Molecular sieve;

DOI:10.1038/ja.2012.124

Reference yield:

C27H54O9Si2 → (5S,6R,9R)-6-((1,3-dioxolan-2-yl)methyl)-4-methoxy-6,8,9-trimethyl-1-oxaspiro[4.5]deca-3,7-dien-2-one (1428980-16-8) + (1S,2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-1-((Z)-1-methoxy-2-(ethoxycarbonyl)ethenyl)-2,4,5-trimethylcyclohex-3-en-1-ol (1428980-17-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 4-methylmorpholine N-oxide / dichloromethane / 0.17 h / 20 °C / Inert atmosphere; Molecular sieve

1.2: 1 h / 20 °C / Inert atmosphere; Molecular sieve

2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 - 0 °C

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.75 h / -18 - 20 °C / Inert atmosphere

4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

5.1: magnesium; ethylene dibromide / tetrahydrofuran / 1 h / Inert atmosphere; Reflux

5.2: 1 h / 20 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 18 h / 80 °C / Inert atmosphere

8.1: tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

8.2: 1 h / -78 °C / Inert atmosphere

9.1: sodium methylate / methanol / 34.5 h / 20 - 60 °C / Inert atmosphere; Molecular sieve

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; n-butyllithium; sodium methylate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; magnesium; 4-methylmorpholine N-oxide; ethylene dibromide; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;

DOI:10.1038/ja.2012.124

Reference yield:

(R)-2,3-dimethyl-1,3-butanediol (73295-16-6) → (5S,6R,9R)-6-((1,3-dioxolan-2-yl)methyl)-4-methoxy-6,8,9-trimethyl-1-oxaspiro[4.5]deca-3,7-dien-2-one (1428980-16-8) + (1S,2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-1-((Z)-1-methoxy-2-(ethoxycarbonyl)ethenyl)-2,4,5-trimethylcyclohex-3-en-1-ol (1428980-17-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyridine / 15 h / 0 °C

2.1: methanesulfonyl chloride; triethylamine / diethyl ether / 15 h / 0 °C / Inert atmosphere

3.1: lithium bromide / tetrahydrofuran / 3.5 h / Inert atmosphere; Reflux

4.1: magnesium; ethylene dibromide / tetrahydrofuran / 1 h / Inert atmosphere; Reflux

4.2: 1 h / 20 °C / Inert atmosphere

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 18 h / 80 °C / Inert atmosphere

7.1: tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

7.2: 1 h / -78 °C / Inert atmosphere

8.1: sodium methylate / methanol / 34.5 h / 20 - 60 °C / Inert atmosphere; Molecular sieve

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium methylate; sodium hydrogencarbonate; Dess-Martin periodane; magnesium; methanesulfonyl chloride; ethylene dibromide; triethylamine; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene;

DOI:10.1038/ja.2012.124

upstream raw materials:

(2R)-2-((1,3-dioxolan-2-yl)methyl)-2-methylbut-3-en-1-ol

(S)-2,3-dimethylbut-3-en-1-yl 4-methylbenzenesulfonate

(3S)-4-bromo-2,3-dimethylbut-1-ene

(2R)-2-((1,3-dioxolan-2-yl)methyl)-2-methylbut-3-enal

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