(1S,2S,3S,6R)-3-benzoyloxy-2-hydroxy-4,8,8-trimethyl-7,9-dioxabicyclo[4.3.0]non-4-ene

Base Information

• Chemical Name: (1S,2S,3S,6R)-3-benzoyloxy-2-hydroxy-4,8,8-trimethyl-7,9-dioxabicyclo[4.3.0]non-4-ene
• CAS No.: 1134474-72-8
• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.343

Synonyms:(1S,2S,3S,6R)-3-benzoyloxy-2-hydroxy-4,8,8-trimethyl-7,9-dioxabicyclo[4.3.0]non-4-ene

Chemical Property of (1S,2S,3S,6R)-3-benzoyloxy-2-hydroxy-4,8,8-trimethyl-7,9-dioxabicyclo[4.3.0]non-4-ene

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Technology Process of (1S,2S,3S,6R)-3-benzoyloxy-2-hydroxy-4,8,8-trimethyl-7,9-dioxabicyclo[4.3.0]non-4-ene

There total 1 articles about (1S,2S,3S,6R)-3-benzoyloxy-2-hydroxy-4,8,8-trimethyl-7,9-dioxabicyclo[4.3.0]non-4-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: 97.0%

3-benzoyl-1,2,7,8-tetradeoxy-5,6-O-isopropylidene-2-C-methyl-D-allo-octa-1,7-dienitol (1134474-68-2) → (1S,2S,3S,6R)-3-benzoyloxy-2-hydroxy-4,8,8-trimethyl-7,9-dioxabicyclo[4.3.0]non-4-ene (1134474-72-8)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 96h; Reflux; Inert atmosphere; Darkness;

DOI:10.1002/ejoc.200800983

Reference yield: 75.0%

3,4-dihydro-2H-pyran (110-87-2) + (1S,2S,3S,6R)-3-benzoyloxy-2-hydroxy-4,8,8-trimethyl-7,9-dioxabicyclo[4.3.0]non-4-ene (1134474-72-8) → (1R,2S,3S,6R)-3-benzoyloxy-4,8,8-trimethyl-2-tetrahydropyranyloxy-7,9-dioxabicyclo[4.3.0]non-4-ene (1134474-79-5)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.200800983

Reference yield:

trifluoromethylsulfonic anhydride (358-23-6) + (1S,2S,3S,6R)-3-benzoyloxy-2-hydroxy-4,8,8-trimethyl-7,9-dioxabicyclo[4.3.0]non-4-ene (1134474-72-8) → C18H19F3O7S

Guidance literature:

With pyridine; In dichloromethane; at -20 - 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/ejoc.200800983

upstream raw materials:

3-benzoyl-1,2,7,8-tetradeoxy-5,6-O-isopropylidene-2-C-methyl-D-allo-octa-1,7-dienitol

Downstream raw materials:

(1R,2S,3S,6R)-3-benzoyloxy-4,8,8-trimethyl-2-tetrahydropyranyloxy-7,9-dioxabicyclo[4.3.0]non-4-ene

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