(1R,5R,6S,7R)-5-Benzyloxymethoxy-2,2,6-trimethyl-8-methylene-11-oxa-tricyclo[5.3.2.0^1,6]dodec-9-ene

Base Information

• Chemical Name: (1R,5R,6S,7R)-5-Benzyloxymethoxy-2,2,6-trimethyl-8-methylene-11-oxa-tricyclo[5.3.2.0^1,6]dodec-9-ene
• CAS No.: 120666-93-5
• Molecular Formula: C₂₃H₃₀O₃
• Molecular Weight: 354.489

Synonyms:(1R,5R,6S,7R)-5-Benzyloxymethoxy-2,2,6-trimethyl-8-methylene-11-oxa-tricyclo[5.3.2.0^1,6]dodec-9-ene

Chemical Property of (1R,5R,6S,7R)-5-Benzyloxymethoxy-2,2,6-trimethyl-8-methylene-11-oxa-tricyclo[5.3.2.0^1,6]dodec-9-ene

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Technology Process of (1R,5R,6S,7R)-5-Benzyloxymethoxy-2,2,6-trimethyl-8-methylene-11-oxa-tricyclo[5.3.2.0^1,6]dodec-9-ene

There total 9 articles about (1R,5R,6S,7R)-5-Benzyloxymethoxy-2,2,6-trimethyl-8-methylene-11-oxa-tricyclo[5.3.2.0^1,6]dodec-9-ene 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: 60.0%

(1R,5R,6S,7R,8R)-5-Benzyloxymethoxy-2,2,6,8-tetramethyl-11-oxa-tricyclo[5.3.2.01,6]dodec-9-en-8-ol (120666-91-3) → (1R,5R,6S,7R)-5-Benzyloxymethoxy-2,2,6-trimethyl-8-methylene-11-oxa-tricyclo[5.3.2.01,6]dodec-9-ene (120666-93-5) + (1R,5R,6S,7R)-5-Benzyloxymethoxy-2,2,6,8-tetramethyl-11-oxa-tricyclo[5.3.2.01,6]dodec-8-en-10-one (120666-92-4)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; Title compound not separated from byproducts;

DOI:10.1021/jo00272a005

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (1R,5R,6S,7R)-5-Benzyloxymethoxy-2,2,6-trimethyl-8-methylene-11-oxa-tricyclo[5.3.2.01,6]dodec-9-ene (120666-93-5)

Guidance literature:

Multi-step reaction with 6 steps

1: iPr₂NEt / CH₂Cl₂

2: NaH / tetrahydrofuran / Heating

3: 70 percent / N,N-dimethylaniline / 240 °C

4: LiAlH₄ / diethyl ether

5: tBuOOH, VO(acac)2 / benzene

6: 1.) PCC, 2.) Al-Hg, H₂O / 1.) CH₂Cl₂, 2.) THF

With tert.-butylhydroperoxide; lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; aluminium amalgam; water; sodium hydride; N,N-dimethyl-aniline; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo00272a005

Reference yield:

4-(3-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-3-en-2-one (14398-34-6) → (1R,5R,6S,7R)-5-Benzyloxymethoxy-2,2,6-trimethyl-8-methylene-11-oxa-tricyclo[5.3.2.01,6]dodec-9-ene (120666-93-5)

Guidance literature:

Multi-step reaction with 6 steps

1: iPr₂NEt / CH₂Cl₂

2: NaH / tetrahydrofuran / Heating

3: 70 percent / N,N-dimethylaniline / 240 °C

4: LiAlH₄ / diethyl ether

5: tBuOOH, VO(acac)2 / benzene

6: 1.) PCC, 2.) Al-Hg, H₂O / 1.) CH₂Cl₂, 2.) THF

With tert.-butylhydroperoxide; lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; aluminium amalgam; water; sodium hydride; N,N-dimethyl-aniline; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo00272a005

upstream raw materials:

(1R,5R,6S,7R,8R)-5-Benzyloxymethoxy-2,2,6,8-tetramethyl-11-oxa-tricyclo[5.3.2.0^1,6]dodec-9-en-8-ol

Benzyloxymethyl chloride

4-(3-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-3-en-2-one

(E)-4-(3-Benzyloxymethoxy-2,6,6-trimethyl-cyclohex-1-enyl)-but-3-en-2-one

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