trans-(1S,5'R)-1-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-3-phenyl-prop-2-en-ol

Base Information

• Chemical Name: trans-(1S,5'R)-1-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-3-phenyl-prop-2-en-ol
• CAS No.: 267665-95-2
• Molecular Formula: C₁₄H₁₈O₃
• Molecular Weight: 234.295

Synonyms:trans-(1S,5'R)-1-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-3-phenyl-prop-2-en-ol

Chemical Property of trans-(1S,5'R)-1-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-3-phenyl-prop-2-en-ol

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Technology Process of trans-(1S,5'R)-1-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-3-phenyl-prop-2-en-ol

There total 9 articles about trans-(1S,5'R)-1-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-3-phenyl-prop-2-en-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: 87.0%

(1S,5'R)-1-(2',2'-dimethyl-[1',3']dioxolan-4-yl)-3-phenyl-prop-2-yn-ol (208114-17-4) → trans-(1S,5'R)-1-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-3-phenyl-prop-2-en-ol (267665-95-2)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; at 20 ℃; for 1h;

DOI:10.1002/jccs.200000004

Reference yield: 85.0%

C11H14O3 + 2,2-dimethoxy-propane (77-76-9) → ((4S,5S)-2,2-dimethyl-5-((E)-styryl)-1,3-dioxolan-4-yl)methanol (127743-12-8) + trans-(1S,5'R)-1-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-3-phenyl-prop-2-en-ol (267665-95-2)

Guidance literature:

With toluene-4-sulfonic acid; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.0c03929

Reference yield:

trans-(2R,3R)-2-benzylsulfonyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)oxirane (889862-53-7) → cis-(1S,5'R)-1-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-3-phenyl-prop-2-en-ol (267665-93-0) + trans-(1S,5'R)-1-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-3-phenyl-prop-2-en-ol (267665-95-2)

Guidance literature:

With lithium tert-butoxide; In tetrahydrofuran; at 20 ℃; for 36h;

DOI:10.1002/ejoc.200500956

upstream raw materials:

(1S,5'R)-1-(2',2'-dimethyl-[1',3']dioxolan-4-yl)-3-phenyl-prop-2-yn-ol

trans-(2R,3R)-2-benzylsulfonyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)oxirane

trans-2-benzylsulfonyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)ethene

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

Downstream raw materials:

trans-(1S,5'R)-1-diazoacetic acid 1-(2',2'-dimethyl-[1',3']dioxolane-4'-yl)-3-phenyl-prop-2-enyl ester

(2R,3S)-trans-5-phenyl-4-penten-1,2,3-triol

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