(1S,2S,3R,7R,9S)-2,5,5,10,10-Pentamethyl-3-((E)-styryl)-4,6-dioxa-tricyclo[7.1.1.0^2,7]undecane

Base Information

• Chemical Name: (1S,2S,3R,7R,9S)-2,5,5,10,10-Pentamethyl-3-((E)-styryl)-4,6-dioxa-tricyclo[7.1.1.0^2,7]undecane
• CAS No.: 178435-81-9
• Molecular Formula: C₂₂H₃₀O₂
• Molecular Weight: 326.479

Synonyms:(1S,2S,3R,7R,9S)-2,5,5,10,10-Pentamethyl-3-((E)-styryl)-4,6-dioxa-tricyclo[7.1.1.0^2,7]undecane

Chemical Property of (1S,2S,3R,7R,9S)-2,5,5,10,10-Pentamethyl-3-((E)-styryl)-4,6-dioxa-tricyclo[7.1.1.0^2,7]undecane

Chemical Property:

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Technology Process of (1S,2S,3R,7R,9S)-2,5,5,10,10-Pentamethyl-3-((E)-styryl)-4,6-dioxa-tricyclo[7.1.1.0^2,7]undecane

There total 2 articles about (1S,2S,3R,7R,9S)-2,5,5,10,10-Pentamethyl-3-((E)-styryl)-4,6-dioxa-tricyclo[7.1.1.0^2,7]undecane 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:

(1S,2R,3R,6R,8R)-2,9,9-Trimethyl-3-((E)-styryl)-5-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-4-oxa-5-bora-tricyclo[6.1.1.02,6]decane (178435-67-1) → (1S,2S,3R,7R,9S)-2,5,5,10,10-Pentamethyl-3-((E)-styryl)-4,6-dioxa-tricyclo[7.1.1.02,7]undecane (178435-81-9)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂O₂; NaOH

2: PPTS

With sodium hydroxide; dihydrogen peroxide; pyridinium p-toluenesulfonate; 1: Oxidation / 2: Condensation;

DOI:10.1021/ja991161+

Reference yield:

2,2-dimethoxy-propane (77-76-9) + (1S,2S,3R,5S)-2-((E)-(R)-1-Hydroxy-3-phenyl-allyl)-2,6,6-trimethyl-bicyclo[3.1.1]heptan-3-ol (178435-78-4) → (1S,2S,3R,7R,9S)-2,5,5,10,10-Pentamethyl-3-((E)-styryl)-4,6-dioxa-tricyclo[7.1.1.02,7]undecane (178435-81-9)

Guidance literature:

With pyridinium p-toluenesulfonate;

DOI:10.1021/ja991161+

Reference yield: 93.0%

methanol (67-56-1) + (1S,2S,3R,7R,9S)-2,5,5,10,10-Pentamethyl-3-((E)-styryl)-4,6-dioxa-tricyclo[7.1.1.02,7]undecane (178435-81-9) → (1S,2S,3R,7R,9S)-3-[(1S)-2,2-dimethoxy-1-phenylethyl]-2,5,5,10,10-pentamethyl-4,6-dioxatricyclo[7.1.1.02,7]undecane

Guidance literature:

With boron trifluoride diethyl etherate; [bis(pyridine)iodine]⁺ tetrafluoroborate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/chem.200500070

upstream raw materials:

2,2-dimethoxy-propane

(1S,2S,3R,5S)-2-((E)-(R)-1-Hydroxy-3-phenyl-allyl)-2,6,6-trimethyl-bicyclo[3.1.1]heptan-3-ol

(1S,2R,3R,6R,8R)-2,9,9-Trimethyl-3-((E)-styryl)-5-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-4-oxa-5-bora-tricyclo[6.1.1.0^2,6]decane

Downstream raw materials:

(1S,2S,3S,7R,9S)-3-[(1S,2S)-1-iodo-2-methoxy-2-phenylethyl]-2,5,5,10,10-pentamethyl-4,6-dioxatricyclo[7.1.1.0^2,7]undecane

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