(1S,2S,5R,6R,7R)-5-Benzyloxymethyl-2-methyl-8,9-dioxa-tricyclo[5.2.2.0^2,6]undec-10-ene

Base Information

• Chemical Name: (1S,2S,5R,6R,7R)-5-Benzyloxymethyl-2-methyl-8,9-dioxa-tricyclo[5.2.2.0^2,6]undec-10-ene
• CAS No.: 164225-18-7
• Molecular Formula: C₁₈H₂₂O₃
• Molecular Weight: 286.371

Synonyms:(1S,2S,5R,6R,7R)-5-Benzyloxymethyl-2-methyl-8,9-dioxa-tricyclo[5.2.2.0^2,6]undec-10-ene

Chemical Property of (1S,2S,5R,6R,7R)-5-Benzyloxymethyl-2-methyl-8,9-dioxa-tricyclo[5.2.2.0^2,6]undec-10-ene

Chemical Property:

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Technology Process of (1S,2S,5R,6R,7R)-5-Benzyloxymethyl-2-methyl-8,9-dioxa-tricyclo[5.2.2.0^2,6]undec-10-ene

There total 1 articles about (1S,2S,5R,6R,7R)-5-Benzyloxymethyl-2-methyl-8,9-dioxa-tricyclo[5.2.2.0^2,6]undec-10-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: 83.0%

(1R,3aR,7aR)-1-Benzyloxymethyl-3a-methyl-2,3,3a,7a-tetrahydro-1H-indene → (1S,2S,5R,6R,7R)-5-Benzyloxymethyl-2-methyl-8,9-dioxa-tricyclo[5.2.2.02,6]undec-10-ene (164225-18-7)

Guidance literature:

With oxygen; rose bengal; In isopropyl alcohol; at 23 ℃; for 11h; Irradiation;

DOI:10.1016/0957-4166(95)00072-W

Reference yield:

(1S,2S,5R,6R,7R)-5-Benzyloxymethyl-2-methyl-8,9-dioxa-tricyclo[5.2.2.02,6]undec-10-ene (164225-18-7) → (3R,3aR,7S,7aS)-3-Benzyloxymethyl-7-hydroxy-7a-methyl-1,2,3,3a,7,7a-hexahydro-inden-4-one + (1R,3aS,7R,7aR)-1-Benzyloxymethyl-7-hydroxy-3a-methyl-1,2,3,3a,7,7a-hexahydro-inden-4-one (164225-19-8)

Guidance literature:

With triethylamine; In dichloromethane; at 30 - 35 ℃; for 90h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/0957-4166(95)00072-W

Reference yield:

acetic anhydride (108-24-7) + (1S,2S,5R,6R,7R)-5-Benzyloxymethyl-2-methyl-8,9-dioxa-tricyclo[5.2.2.02,6]undec-10-ene (164225-18-7) → Acetic acid (1R,3aS,4S,7S,7aR)-1-benzyloxymethyl-7-hydroxy-3a-methyl-octahydro-inden-4-yl ester + Acetic acid (3R,3aR,4R,7R,7aS)-3-benzyloxymethyl-7-hydroxy-7a-methyl-octahydro-inden-4-yl ester

Guidance literature:

With pyridine; dmap; sodium tetrahydroborate; triethylamine; Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1016/0957-4166(95)00072-W

Downstream raw materials:

(1R,3aS,7R,7aR)-1-Benzyloxymethyl-7-hydroxy-3a-methyl-1,2,3,3a,7,7a-hexahydro-inden-4-one

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