(1S,5R)-cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanemethanol

Base Information

• Chemical Name: (1S,5R)-cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanemethanol
• CAS No.: 171231-07-5
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.252
• Mol file: 171231-07-5.mol

Synonyms:(1S,5R)-cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanemethanol

Chemical Property of (1S,5R)-cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanemethanol

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (1S,5R)-cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanemethanol

There total 15 articles about (1S,5R)-cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanemethanol 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: 95.0%

(1S,5R)-8,8-dimethyl-2-methylene-6-oxabicyclo[3.2.1]octan-7-one (106036-74-2) → (1S,5R)-cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanemethanol (171231-07-5)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 - 20 ℃; for 1.5h;

DOI:10.1016/S0040-4020(00)00645-1

Reference yield: 50.0%

(R,E)-((5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-yl)oxy)trimethylsilane (171231-05-3) → (1S,5R)-cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanemethanol (171231-07-5) + 3(S)-(Hydroxymethyl)-2,2,4-trimethylcyclohex-3-en-1(R)-ol (171231-04-2)

Guidance literature:

With tin(IV) chloride; In dichloromethane; toluene; at 0 ℃; for 1h; Yield given. Title compound not separated from byproducts;

DOI:10.1021/jo00127a028

Reference yield: 7.0%

vinyl acetate (108-05-4,9003-20-7) + (1RS,3SR)-3-(hydroxymethyl)-2,2-dimethyl-4-methylenecyclohexanol (72445-03-5,85121-46-6) → C12H20O3 + C12H20O3 + C12H20O3 (1178893-08-7) + C12H20O3 + C14H22O4 (1178893-12-3) + (1'R,3'S)-(+)-cis-(3'-hydroxy-2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methanol (475197-90-1) + (1S,5R)-cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanemethanol (171231-07-5)

Guidance literature:

With Pseudomonas cepacia lipase; In tert-butyl methyl ether; at 20 ℃; optical yield given as %ee; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.tetasy.2009.05.013

upstream raw materials:

(R,E)-((5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-yl)oxy)trimethylsilane

(1S,5R)-8,8-dimethyl-2-methylene-6-oxabicyclo[3.2.1]octan-7-one

4-hydroxy-3-methyl-cyclohex-2-en-1-one

(R)-4-hydroxy-3-methyl-cyclohex-2-en-1-one