(-)-diethyl ((1R,2R,3R,6R,7R)-10-ethylenedioxy-6-methyltricyclo<5.3.0.0^2,6>decan-3-yl)malonate

Base Information

• Chemical Name: (-)-diethyl ((1R,2R,3R,6R,7R)-10-ethylenedioxy-6-methyltricyclo<5.3.0.0^2,6>decan-3-yl)malonate
• CAS No.: 84077-38-3
• Molecular Formula: C₂₀H₃₀O₆
• Molecular Weight: 366.455

Synonyms:(-)-diethyl ((1R,2R,3R,6R,7R)-10-ethylenedioxy-6-methyltricyclo<5.3.0.0^2,6>decan-3-yl)malonate

Chemical Property of (-)-diethyl ((1R,2R,3R,6R,7R)-10-ethylenedioxy-6-methyltricyclo<5.3.0.0^2,6>decan-3-yl)malonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-diethyl ((1R,2R,3R,6R,7R)-10-ethylenedioxy-6-methyltricyclo<5.3.0.0^2,6>decan-3-yl)malonate

There total 1 articles about (-)-diethyl ((1R,2R,3R,6R,7R)-10-ethylenedioxy-6-methyltricyclo<5.3.0.0^2,6>decan-3-yl)malonate 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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (-)-diethyl ((1R,2R,3R,6R,7R)-10-ethylenedioxy-6-methyltricyclo<5.3.0.02,6>decan-3-yl)malonate (84077-38-3)

Guidance literature:

Multi-step reaction with 8 steps

2: cc HCl / methanol

3: pyridine / methanol

4: 25 percent / Irradiation

5: 95 percent

7: 2.) NaBH₄ / 1.)Pd/C in AcOEt; 2.) MeOH

8: 1.)tosylation 2.) refluxing DME

With pyridine; hydrogenchloride; sodium tetrahydroborate; In methanol;

DOI:10.1016/S0040-4039(00)87626-1

Reference yield:

(-)-diethyl ((1R,2R,3R,6R,7R)-10-ethylenedioxy-6-methyltricyclo<5.3.0.02,6>decan-3-yl)malonate (84077-38-3) → (1S,3aS,3bR,6aS,6bR)-1-Isopropyl-3a-methyl-6-methylene-decahydro-cyclobutadicyclopentene (5208-59-3,13828-08-5,68036-15-7,78148-76-2,92998-16-8,119903-95-6,135355-71-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / LAH / diethyl ether / 2 h / Ambient temperature

2: pyridin / 36 h / Ambient temperature

3: 78 percent / LiAlH₄ / tetrahydrofuran / 1.8 h / Heating

4: 82 percent / p-toluenesulfonic acid / acetone / 23 h / Ambient temperature

5: 98 percent / BuLi / hexane; diethyl ether / 20 h / Ambient temperature

With pyridine; lithium aluminium tetrahydride; n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; acetone;

Reference yield:

(-)-diethyl ((1R,2R,3R,6R,7R)-10-ethylenedioxy-6-methyltricyclo<5.3.0.02,6>decan-3-yl)malonate (84077-38-3) → (-)-β-bourbonene (5208-59-3,13828-08-5,68036-15-7,78148-76-2,92998-16-8,119903-95-6,135355-71-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / LiAlH₄

2: 1.) LiAlH₄ 2.) p-TsOH / 2.) acetone

3: 98 percent

With lithium aluminium tetrahydride; toluene-4-sulfonic acid;

DOI:10.1016/S0040-4039(00)87626-1

upstream raw materials:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Downstream raw materials:

(1S,3aS,3bR,6aS,6bR)-1-Isopropyl-3a-methyl-6-methylene-decahydro-cyclobutadicyclopentene

(-)-β-bourbonene

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