40940-58-7

Upstream product

• 2216-51-5 (-)-menthol 
• 106-95-6 allyl bromide 
• 556-56-9 allyl iodid 
• 136375-73-0 [[[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl]oxy]methyl]benzene 
• 101-37-1 triallyl cyanurate 
• 15356-70-4 menthol 
• 753488-83-4 (1S,2R,4R)-2-(2,3-dimethylbut-2-en-1-yloxy)-1-isopropyl-4-methylcyclohexane 
• 195863-85-5 (1S,2R,4R)-1-isopropyl-4-methyl-2-(2-methylprop-2-en-1-yloxy)cyclohexane 
• 180477-54-7 (1S,2R,4R)-1-isopropyl-4-methyl-2-(3-methylbut-2-en-1-yloxy)cyclohexane 
• 27303-99-7 sodium menthoxide 

Downstream Products

• 76993-59-4 (-)-(1'R,2'S,5'R)-1-(2'-isopropyl-5'-methylcyclohexyloxy)acetaldehyde 
• 19876-19-8 Menthoxypropyl-methyl-dichlor-silan 
• 19876-26-7 ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-[3-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-propyl]-dimethyl-silane 
• 19876-20-1 Chloro-[3-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-propyl]-dimethyl-silane 
• 19876-21-2 Dichloro-[3-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-propyl]-phenyl-silane 
• 19876-22-3 Menthoxypropyl-trichlor-silan 
• 2216-51-5 (-)-menthol 
• 107941-60-6 (1S,2R,4R)-1-isopropyl-4-methyl-2-((Z)-prop-1-en-1-yloxy)cyclohexane 
• 19876-23-4 Ethoxy-[3-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-propyl]-dimethyl-silane 
• 19876-24-5 Diethoxy-[3-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-propyl]-methyl-silane 
• 19876-31-4 1,3-Bis-[3-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-propyl]-1,1,3,3-tetramethyl-disiloxane 
• 19876-25-6 triethoxy(3-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)- propyl)silane 
• 107941-60-6 (1S,2R,4R)-1-Isopropyl-4-methyl-2-[((E)-propenyl)oxy]-cyclohexane 
• 1204045-48-6 2-N-phenoxyacetyl-6-(3-O-L-menthylpropenyl)-9-(3',5'-di-O-t-butyldimethylsilyl-2'-deoxy-β-D-ribofuranosyl)purine 

Relevant academic research and scientific papers

Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization

This report discloses the deallylation of O - and N -allyl functional groups by using a combination of a Ni-H precatalyst and excess Bronsted acid. Key steps are the isomerization of the O - or N -allyl group through Ni-catalyzed double-bond migration followed by Bronsted acid induced O/N-C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.

Reliably Regioselective Dialkyl Ether Cleavage with Mixed Boron Trihalides

A protocol for the regioselective cleavage of unsymmetrical alkyl ethers to generate alkyl alcohol and alkyl bromide products is described. A mixture of trihaloboranes triggers this conversion and exhibits improved reactivity profiles (regioselectivity and yield) compared with BBr3 alone. Additionally, this procedure allows the efficient synthesis of (B-Cl) dialkyl boronate esters. There are limited methods to generate acyclic dialkoxyboryl chlorides, and these intermediates constitute important synthons in main-group chemistry.

Study of O-allylation using triazine-based reagents

Acid-catalyzed allylating reagent 2,4,6-tris(allyloxy)-1,3,5-triazine (TriAT-allyl) and its substituted derivatives have been developed. The reaction of acid-, and alkali-labile alcohols with these reagents in the presence of a catalytic amount of trifluoromethanesulfonic acid (TfOH) afforded the corresponding allyl ethers in good yields. Reactions using these reagents with an unsymmetrically-substituted regioisometric allyl group suggested that a single isometric allylic cation species would be involved.

Isomerization of allyl ethers initiated by lithium diisopropylamide

Lithium diisopropylamide (LDA) promotes virtually quantitative conversion of allylic ethers to (Z)-propenyl ethers. It was discovered that allylic ethers can be isomerized efficiently with very high stereoselectivity to (Z)-propenyl ethers by LDA in THF a

The synthesis of a menthol derivative of 2-aminopurine as a fluorescent DNA lesion

An efficient synthetic route to the phosphoramidite of a menthol functionalized guanosine analog is presented. Two procedures were executed for the key introduction of the 6′-allyl menthyl moiety. Stille vinylation on 6-O-tosylguanosine followed by cross-

Allyl, methallyl, prenyl, and methylprenyl ethers as protected alcohols: Their selective cleavage with diphenyldisulfone under neutral conditions

Diphenyldisulfone is a mild and efficient reagent for selective cleavage of methylprenyl (2,3-dimethylbut-2-en-1-yl), prenyl (3-methylbut-2-en1-yl), and methallyl (2-methylallyl) ethers. These reaction conditions are compatible with the presence of other protecting groups such as acetals, acetates, and allyl, benzyl, and TBDMS ethers. Exposure of 2,3-dimethylbut-2-en-1-yl and 3-methylbut-2-en1-yl ethers to diphenyldisulfone led to the formation of 2,3-dimethylbuta-1,3-diene and isoprene, respectively. 2-Methylallyl ethers undergo isomerization to 2-methylpropenyl ethers, which are easily hydrolyzed into the corresponding free alcohols and isobutyraldehyde.

Oxidative deprotection of allyl glycosides

Allyl glycosides can be deprotected under the condition of the Kharasch- Sosnovsky reaction and by photoinduced reaction with di-(t)butylperoxide in the presence of bromotrichloromethane.

A (-)-Menthyl Bonded Silica Phase for Chiral Separations: Synthesis and Solid State NMR Characterization

A new (-)-menthyl bonded silica phase has been prepared by hydrosilation of a hydride silica intermediate. The hydride silica intermediate was synthesized by the reaction of a monoalkoxysilane (CH3)2SiH(OEt) with silica gel, yielding a relatively high surface coverage (4.4 μmol/m2) of SiH groups. This intermediate was then used successfully in the preparation of a monomeric (-)-menthyl bonded silica phase. The bonded phase produced has been used for the Chromatographic separation of enantiomers in a reversed phase mode (chiral separations). Solid state 13C and 29Si CP-MAS NMR spectroscopy and DRIFT spectroscopy provides valuable information on the structure of the different surface species formed on silica after modification. The surface coverage of the hydride silica intermediate and of the final bonded silica phase produced are also determined. It is found that this modification procedure can exclusively produce a monomeric coverage of SiH groups on the silica surface and can further produce a final monomeric bonded organic silica phase for the separation of enantiomers.

Reductive deprotection of allyl, benzyl and sulfonyl substituted alcohols, amines and amides using a naphthalene-catalysed lithiation

The reaction of different protected alcohols, amines and amides with lithium and a catalytic amount of naphthalene (4 mol %) in THF at low temperature leads to their deprotection under very mild reaction conditions, the process being in many cases chemoselective.

Preparation and use of chiral (Z)-enol ethers in asymmetric Bradsher cycloaddition

Chiral (Z)-enol ethers 7a-7p have been prepared in two steps. Bradsher cycloaddition between such compounds and 2,7-naphthyridinium salt 4b in water or in ter-butanol-water afforded, in some cases with good yield and diastereoselectivity, highly functionalized isoquinoline derivatives, potential intermediates in Manzamine A 1 total synthesis. X-Ray analysis secured the direction of asymmetric induction with enol ether 7l.