6α-Benzyloxy-4β,8β-epoxy-4,5,8,8a-tetrahydro-3-phenyl-(3a-αH,8a-αH)-3aH-cycloheptaisoxazol

Base Information

• Chemical Name: 6α-Benzyloxy-4β,8β-epoxy-4,5,8,8a-tetrahydro-3-phenyl-(3a-αH,8a-αH)-3aH-cycloheptaisoxazol
• CAS No.: 139781-11-6
• Molecular Formula: C₂₁H₂₁NO₃
• Molecular Weight: 335.403

Synonyms:6α-Benzyloxy-4β,8β-epoxy-4,5,8,8a-tetrahydro-3-phenyl-(3a-αH,8a-αH)-3aH-cycloheptaisoxazol

Chemical Property of 6α-Benzyloxy-4β,8β-epoxy-4,5,8,8a-tetrahydro-3-phenyl-(3a-αH,8a-αH)-3aH-cycloheptaisoxazol

Chemical Property:

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Technology Process of 6α-Benzyloxy-4β,8β-epoxy-4,5,8,8a-tetrahydro-3-phenyl-(3a-αH,8a-αH)-3aH-cycloheptaisoxazol

There total 3 articles about 6α-Benzyloxy-4β,8β-epoxy-4,5,8,8a-tetrahydro-3-phenyl-(3a-αH,8a-αH)-3aH-cycloheptaisoxazol 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: 65.0%

3α-Benzyloxy-(1-αH,5-αH)-8-oxabicyclo<3.2.1>oct-6-en (139882-20-5) + benzohydroximoyl chloride (698-16-8) → 6α-Benzyloxy-4β,8β-epoxy-4,5,8,8a-tetrahydro-3-phenyl-(3a-αH,8a-αH)-3aH-cycloheptaisoxazol (139781-11-6)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 8h; Ambient temperature;

DOI:10.1002/ardp.19923250205

Reference yield:

8-oxabicyclo[3.2.1]oct-6-en-3-one (40458-77-3) → 6α-Benzyloxy-4β,8β-epoxy-4,5,8,8a-tetrahydro-3-phenyl-(3a-αH,8a-αH)-3aH-cycloheptaisoxazol (139781-11-6)

Guidance literature:

Multi-step reaction with 3 steps

1: K-Selektride / tetrahydrofuran / 4 h / -75 °C

2: 1) NaH / 1) THF, RT, 0.5h, 2) 2.5h, reflux

3: 65 percent / NEt₃ / tetrahydrofuran / 8 h / Ambient temperature

With sodium hydride; potassium tri-sec-butyl-borohydride; triethylamine; In tetrahydrofuran;

DOI:10.1002/ardp.19923250205

Reference yield:

endo-8-oxabicyclo[3.2.1]oct-6-en-3-ol (89858-82-2,99327-44-3,99327-43-2) → 6α-Benzyloxy-4β,8β-epoxy-4,5,8,8a-tetrahydro-3-phenyl-(3a-αH,8a-αH)-3aH-cycloheptaisoxazol (139781-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) NaH / 1) THF, RT, 0.5h, 2) 2.5h, reflux

2: 65 percent / NEt₃ / tetrahydrofuran / 8 h / Ambient temperature

With sodium hydride; triethylamine; In tetrahydrofuran;

DOI:10.1002/ardp.19923250205

upstream raw materials:

3α-Benzyloxy-(1-αH,5-αH)-8-oxabicyclo<3.2.1>oct-6-en

benzohydroximoyl chloride

8-oxabicyclo[3.2.1]oct-6-en-3-one

endo-8-oxabicyclo[3.2.1]oct-6-en-3-ol

Downstream raw materials:

3α-Benzyloxy-7β-(aminophenylmethyl)-(1-αH,5-αH)-8-oxabicyclo<3.2.1>octan-6β-ol

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