(1R,5S,6R,8R)-5-tert-Butoxy-6-methyl-9,12-dioxa-tricyclo[6.3.1.0^1,6]dodec-10-ene

Base Information

• Chemical Name: (1R,5S,6R,8R)-5-tert-Butoxy-6-methyl-9,12-dioxa-tricyclo[6.3.1.0^1,6]dodec-10-ene
• CAS No.: 155095-75-3
• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.354

Synonyms:(1R,5S,6R,8R)-5-tert-Butoxy-6-methyl-9,12-dioxa-tricyclo[6.3.1.0^1,6]dodec-10-ene

Chemical Property of (1R,5S,6R,8R)-5-tert-Butoxy-6-methyl-9,12-dioxa-tricyclo[6.3.1.0^1,6]dodec-10-ene

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Technology Process of (1R,5S,6R,8R)-5-tert-Butoxy-6-methyl-9,12-dioxa-tricyclo[6.3.1.0^1,6]dodec-10-ene

There total 1 articles about (1R,5S,6R,8R)-5-tert-Butoxy-6-methyl-9,12-dioxa-tricyclo[6.3.1.0^1,6]dodec-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: 44.0%

(2R,8S,8aS)-8-tert-Butoxy-8a-methyl-1,2,3,5,6,7,8,8a-octahydro-naphthalene-2,3-diol → {(1S,2S)-2-tert-Butoxy-1-methyl-6-[2-oxo-eth-(E)-ylidene]-cyclohexyl}-acetaldehyde + (1R,5S,6R,8S)-5-tert-Butoxy-6-methyl-9,12-dioxa-tricyclo[6.3.1.01,6]dodecan-10-ol + (1R,5S,6R,8R)-5-tert-Butoxy-6-methyl-9,12-dioxa-tricyclo[6.3.1.01,6]dodec-10-ene (155095-75-3)

Guidance literature:

With sodium bismuthate; In water; acetic acid; at 20 ℃; for 19h;

DOI:10.1002/ejoc.200400549

Reference yield:

(1R,5S,6R,8R)-5-tert-Butoxy-6-methyl-9,12-dioxa-tricyclo[6.3.1.01,6]dodec-10-ene (155095-75-3) → (1S,2R,3S)-3-tert-Butoxy-2-(2-hydroxy-ethyl)-1-hydroxymethyl-2-methyl-cyclohexanol (215371-36-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / O₃, pyridine / CH₂Cl₂ / 0.08 h / -78 °C

2: 67 percent / aq. K₂CO₃ / methanol / 6 h / Ambient temperature

3: LiAlH₄ / tetrahydrofuran / 1 h / Heating

With pyridine; lithium aluminium tetrahydride; potassium carbonate; ozone; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0957-4166(98)00289-4

Downstream raw materials:

(1S,2R,3S)-3-tert-Butoxy-2-(2-hydroxy-ethyl)-1-hydroxymethyl-2-methyl-cyclohexanol

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