(1R,3S,6S)-6-((1E,3Z)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-1,5,5-trimethyl-7-oxa-bicyclo[4.1.0]heptan-3-ol

Base Information

Chemical Name:(1R,3S,6S)-6-((1E,3Z)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-1,5,5-trimethyl-7-oxa-bicyclo[4.1.0]heptan-3-ol
CAS No.:69350-47-6
Molecular Formula:C₁₅H₂₄O₃
Molecular Weight:252.354
Hs Code.:

Synonyms:(1R,3S,6S)-6-((1E,3Z)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-1,5,5-trimethyl-7-oxa-bicyclo[4.1.0]heptan-3-ol

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Chemical Property of (1R,3S,6S)-6-((1E,3Z)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-1,5,5-trimethyl-7-oxa-bicyclo[4.1.0]heptan-3-ol

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Technology Process of (1R,3S,6S)-6-((1E,3Z)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-1,5,5-trimethyl-7-oxa-bicyclo[4.1.0]heptan-3-ol

There total 1 articles about (1R,3S,6S)-6-((1E,3Z)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-1,5,5-trimethyl-7-oxa-bicyclo[4.1.0]heptan-3-ol 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:

: 51318-62-8,51371-55-2,26918-14-9
ethyl 4-bromo-3-methylcrotonate

: 69350-47-6
(1R,3S,6S)-6-((1E,3Z)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-1,5,5-trimethyl-7-oxa-bicyclo[4.1.0]heptan-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 1) Zn, I₂ / 1) THF, 0 deg C, 10 min, 2) THF, 30 min

2: 100 percent / CH₃OK / methanol / 18 h / Ambient temperature

4: 86 percent / aq. HClO₄ / tetrahydrofuran / 0.03 h / 4 °C

5: LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature; other reducing agent

With lithium aluminium tetrahydride; perchloric acid; potassium methanolate; iodine; zinc; In tetrahydrofuran; methanol;
DOI:10.1016/S0040-4020(01)80491-9

Reference yield: 100.0%

: 69350-47-6
(1R,3S,6S)-6-((1E,3Z)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-1,5,5-trimethyl-7-oxa-bicyclo[4.1.0]heptan-3-ol

: 8066-07-7,28321-44-0
(1'S,2'R,4'S,2Z,4E)-(1',2'-epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-dienal

Guidance literature:: With manganese(IV) oxide; In dichloromethane; for 2h; Ambient temperature;
DOI:10.1016/S0040-4020(01)80491-9

Reference yield:

: 69350-47-6
(1R,3S,6S)-6-((1E,3Z)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-1,5,5-trimethyl-7-oxa-bicyclo[4.1.0]heptan-3-ol

: 8066-07-7,28321-44-0
(1'S,2'R,4'S,2Z,4E)-(1',2'-epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-dienal

: 28874-44-4,28321-44-0
(1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienal

Guidance literature:: With manganese(IV) oxide; In ethyl acetate; at -10 ℃; for 6h; Yield given. Yields of byproduct given;
DOI:10.1002/hlca.19940770405