(1S,2S,6R)-6-Benzyloxymethyl-2,13-dimethyl-8-oxa-tricyclo[4.4.3.0^1,5]trideca-4,12-dien-9-one

Base Information

• Chemical Name: (1S,2S,6R)-6-Benzyloxymethyl-2,13-dimethyl-8-oxa-tricyclo[4.4.3.0^1,5]trideca-4,12-dien-9-one
• CAS No.: 99268-15-2
• Molecular Formula: C₂₂H₂₆O₃
• Molecular Weight: 338.447

Synonyms:(1S,2S,6R)-6-Benzyloxymethyl-2,13-dimethyl-8-oxa-tricyclo[4.4.3.0^1,5]trideca-4,12-dien-9-one

Chemical Property of (1S,2S,6R)-6-Benzyloxymethyl-2,13-dimethyl-8-oxa-tricyclo[4.4.3.0^1,5]trideca-4,12-dien-9-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,6R)-6-Benzyloxymethyl-2,13-dimethyl-8-oxa-tricyclo[4.4.3.0^1,5]trideca-4,12-dien-9-one

There total 8 articles about (1S,2S,6R)-6-Benzyloxymethyl-2,13-dimethyl-8-oxa-tricyclo[4.4.3.0^1,5]trideca-4,12-dien-9-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: 75.0%

(1S,2S,6R)-6-Benzyloxymethyl-2-methyl-13-methylene-8-oxa-tricyclo[4.4.3.01,5]tridec-4-en-9-one (99268-14-1) → (1S,2S,6R)-6-Benzyloxymethyl-2,13-dimethyl-8-oxa-tricyclo[4.4.3.01,5]trideca-4,12-dien-9-one (99268-15-2)

Guidance literature:

With methanesulfonic acid; In dichloromethane; for 46h; Heating;

DOI:10.1021/ja00310a076

Reference yield:

2-allyl-2-cyclopenten-1-one (51557-85-8) → (1S,2S,6R)-6-Benzyloxymethyl-2,13-dimethyl-8-oxa-tricyclo[4.4.3.01,5]trideca-4,12-dien-9-one (99268-15-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) Me₂LiCu*SMe₂; 2.) 10percent KOH / 1.) Et₂O, -30 deg C; 2.) EtOH, reflux, 40 min

2: dimethylformamide / 2 h / 130 °C

3: 0.17 h / 0 °C

4: 60 percent / 2.) MeOH / 2.) conc. HCl / 1.) Et₂O, -78 deg C, 1 h; 2.) 25 deg C, 2 h

5: 1.) LDA, HMPA / tetrahydrofuran / 1.) -78 deg C; 2.) 25 deg C

6: LiAlH₄ / diethyl ether / 0.25 h / 25 °C

7: 1.) KIO₄, K₂CO₃, KMnO₄; 2.) p-TsOH / 1.) aq. t-BuOH, 25 deg C, 60 h; 2.) C₆H₆, reflux, 20 min

8: 75 percent / CH₃SO₃H / CH₂Cl₂ / 46 h / Heating

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; potassium permanganate; lithium aluminium tetrahydride; potassium metaperiodate; methanesulfonic acid; potassium carbonate; Lithium dimethylcuprate-dimethyl sulfide complex; toluene-4-sulfonic acid; lithium diisopropyl amide; hydrogenchloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00310a076

Reference yield:

(1S,7aS)-7a-Allyl-1-methyl-1,2,3,6,7,7a-hexahydro-inden-5-one (99268-09-4) → (1S,2S,6R)-6-Benzyloxymethyl-2,13-dimethyl-8-oxa-tricyclo[4.4.3.01,5]trideca-4,12-dien-9-one (99268-15-2)

Guidance literature:

Multi-step reaction with 7 steps

1: dimethylformamide / 2 h / 130 °C

2: 0.17 h / 0 °C

3: 60 percent / 2.) MeOH / 2.) conc. HCl / 1.) Et₂O, -78 deg C, 1 h; 2.) 25 deg C, 2 h

4: 1.) LDA, HMPA / tetrahydrofuran / 1.) -78 deg C; 2.) 25 deg C

5: LiAlH₄ / diethyl ether / 0.25 h / 25 °C

6: 1.) KIO₄, K₂CO₃, KMnO₄; 2.) p-TsOH / 1.) aq. t-BuOH, 25 deg C, 60 h; 2.) C₆H₆, reflux, 20 min

7: 75 percent / CH₃SO₃H / CH₂Cl₂ / 46 h / Heating

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium permanganate; lithium aluminium tetrahydride; potassium metaperiodate; methanesulfonic acid; potassium carbonate; toluene-4-sulfonic acid; lithium diisopropyl amide; hydrogenchloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00310a076

upstream raw materials:

(1S,2S,6R)-6-Benzyloxymethyl-2-methyl-13-methylene-8-oxa-tricyclo[4.4.3.0^1,5]tridec-4-en-9-one

2-allyl-2-cyclopenten-1-one

(1S,7aS)-7a-Allyl-1-methyl-1,2,3,6,7,7a-hexahydro-inden-5-one

(1S,7aS)-7a-Allyl-1,5-dimethyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester

Downstream raw materials:

C₁₅H₂₀O₇

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