34675-24-6

Basic information

• Product Name: (-)-DI[(1R)-MENTHYL] FUMARATE
• Synonyms: (-)-DI[(1R)-MENTHYL] FUMARATE;(-)-DIMENTHYL FUMARATE;Bis(2-isopropyl-5-methylcyclohexyl) (2E)-2-butenedioate;Menthol, fumarate (2:1), (1R,3R,4S)-;(E)-2-Butenedioic acid bis[(1R)-5β-methyl-2α-isopropylcyclohexan-1β-yl] ester;Fumaric acid bis[(1R)-2α-isopropyl-5β-methylcyclohexane-1β-yl] ester;Fumaric acid bis[(1R,1β,4S)-p-menthane-3β-yl] ester;Fumaric acid bis[(1R,1β,4α)-p-menthane-3β-yl] ester
• CAS NO: 34675-24-6
• Molecular Formula: C₂₄H₄₀O₄
• Molecular Weight: 392.57
• Product Categories: DID - DINChiral Building Blocks;Alphabetic;D;Esters;Organic Building Blocks
• Mol File: 34675-24-6.mol

Chemical Properties

• Melting Point: 62-64 °C
• Boiling Point: 211 °C5 mm Hg(lit.)
• Flash Point: 214°C
• Appearance: Colorless to off-white/Low Melting Solid or Powder
• Density: 0.9985 (rough estimate)
• Vapor Pressure: 3.43E-06mmHg at 25°C
• Refractive Index: 1.4460 (estimate)
• BRN: 2568525
• CAS DataBase Reference: (-)-DI[(1R)-MENTHYL] FUMARATE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-DI[(1R)-MENTHYL] FUMARATE(34675-24-6)
• EPA Substance Registry System: (-)-DI[(1R)-MENTHYL] FUMARATE(34675-24-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 34675-24-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemical Synthesis:
(-)-DI[(1R)-MENTHYL] FUMARATE is used as a reagent in the organic chemical synthesis of several compounds, including the synthesis of pentacyclic steroids via tandem Stille coupling. This application highlights its importance in the development of complex organic molecules and its potential use in various industries.
Used in Pharmaceutical Industry:
(-)-DI[(1R)-MENTHYL] FUMARATE is used as a key intermediate in the synthesis of Lobucavir (L469360), an antiviral agent. This demonstrates its significance in the development of pharmaceutical compounds and its potential contribution to the treatment of viral infections.

InChI:InChI=1/C24H40O4/c1-15(2)19-9-7-17(5)13-21(19)27-23(25)11-12-24(26)28-22-14-18(6)8-10-20(22)16(3)4/h11-12,15-22H,7-10,13-14H2,1-6H3/b12-11+

Upstream product

• 627-63-4 fumaryl dichloride 
• 2216-51-5 (-)-menthol 
• 34212-60-7 di-<(1R,2S,5R)-(-)-menthyl>maleate 
• 108-31-6 maleic anhydride 
• 110-17-8 (2E)-but-2-enedioic acid 
• 624-49-7 dimethylfumarate 
• 89-78-1 menthol 

Downstream Products

• 138736-91-1 (1S,2R)-3,3-Dimethoxy-cyclobutane-1,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 
• 139012-63-8 (1R,2S)-3,3-Dimethoxy-cyclobutane-1,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 
• 109005-04-1 bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) (1R,2S,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate 
• 125515-26-6 (11S,12S)-9,10-ethane-11,12-dimenthyl carboxylate-9,10-dihydro anthracene 
• 119163-09-6 (2S,3S)-Oxirane-2,3-dicarboxylic acid 2-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 3-methyl ester 
• 119163-10-9 (2S,3S)-Oxirane-2,3-dicarboxylic acid 2-tert-butyl ester 3-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 
• 111832-30-5 (2S,3S)-Oxirane-2,3-dicarboxylic acid bis-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 
• 182127-14-6 (2S,3R,4R)-4,6-Di-thiophen-2-yl-3,4-dihydro-2H-thiopyran-2,3-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 

Relevant articles and documents

Facile Synthesis of Vinyl Copolymers with Optical Activity Arising from the Configuration of Stereogenic Carbon Atoms in the Main Chain

Hydrolytic cleavage of the alkyl side chain auxiliaries from copolymers of diborneyl and dimethyl fumarates each with styrene, yields optically active vinyl copolymers of fumaric acid and styrene in which the chirality is due to the main chain.

Enantioselective Construction of Modular and Asymmetric Baskets

The precise positioning of functional groups about the inner space of abiotic hosts is a challenging task and of interest for developing more effective receptors and catalysts akin to those found in nature. To address it, we herein report a synthetic methodology for preparing basket-like cavitands comprised of three different aromatics as side arms with orthogonal esters at the rim for further functionalization. First, enantioenriched A (borochloronorbornene), B (iodobromonorbornene), and C (boronorbornene) building blocks were obtained by stereoselective syntheses. Second, consecutive A-to-B and then AB-to-C Suzuki–Miyaura (SM) couplings were optimized to give enantioenriched ABC cavitand as the principal product. The robust synthetic protocol allowed us to prepare (a) an enantioenriched basket with three benzene sides and each holding either tBu, Et, or Me esters, (b) both enantiomers of a so-called “spiral staircase” basket with benzene, naphthalene, and anthracene groups surrounding the inner space, and (c) a photo-responsive basket bearing one anthracene and two benzene arms.

Discovery of (E)-5,5-Difluoro-1-[2-[5-(3-fluorophenyl)pyridin-2-yl]vinyl]octahydrospiro(indene-2,5′-oxazolidin)-2′-one as a PAR1 Antagonist

In a previous study, we showed that several octahydroindene derivatives are potent protease activated receptor 1 (PAR1) antagonists. In the current study, we prepared a series of trans-fused 5,5-difulorooctahydroindenes which do not have a C5 stereogenic center, and evaluated their biological activities and metabolic stabilities. Compound 19 in this series, containing a spirooxazolidinone moiety at C2, showed excellent efficacy in both PAR1 binding (IC50 = 70 nM) and human platelet rich plasma (PRP) aggregation (IC50 = 0.19 μM), along with good metabolic stability (R50 = 345.8, 337.2, and 43.4 min in human, rat, and monkey liver microsomes, each), which is comparable to that of vorapaxar. Four stereoisomers of 19 were prepared and evaluated. (1S,2R,3aR,7aR)-5,5-Difluoro-1-[(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]vinyl]octahydrospiro(indene-2,5′-oxazolidin)-2′-one (31) was found to be the most active (IC50 = 21 nM) stereoisomer as PAR1 antagonist. Compound 31 exhibited good in vivo oral PK profiles and significant ex vivo antithrombotic efficacy in cynomolgus monkeys upon oral administration. When the plasma concentration of 31 was maintained above 200 ng/mL, platelet aggregation induced by haTRAP was completely inhibited.

Menthol derivatives, mixture thereof, and preparation method and applications of menthol derivatives

The invention discloses menthol derivatives, a mixture thereof, and a preparation method and applications of the menthol derivatives. Menthol carries out esterification reactions, then molecular design is performed to synthesize the menthol derivatives with a special molecular structure or a special group, and through the modification on the chemical structure, a novel material, which has a highermelting point and low volatility and is applied to temporary cultural relic reinforcement, is provided. The melting points of the menthol derivatives are gradient, the volatile speed of the menthol derivatives is slower than that of menthol, thus the removing of the menthol derivatives is controllable, and the requirements of cultural relic protection can be satisfied. The provided menthol derivatives are used to temporarily strengthen cultural relic onsite, and have a wide application range.

ADENYLYL CYCLASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND METHOD OF USE THEREOF

The present invention relates to novel adenine based inhibitors of adenylyl cyclase of the formula: wherein X, L, R1, R2, R5 are those defined herein. Compounds of the present invention are useful to treat cardiovascular diseases. The present invention also relates to a method of preventing heart failure by administering an effective amount of compound according to the invention following vascular injury and reperfusion therapy.

[6+5] FUSED BICYCLES AS A THROMBIN ANTAGONIST, PROCESS FOR PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE BICYCLES

The present invention relates to the new [6+5] fused bicycle derivatives, pharmaceutically acceptable salts or isomers thereof, processes for preparing the same, and pharmaceutical compositions comprising the same. The [6+5] fused bicycle derivatives can antagonize the thrombin receptor and thus may be effectively used for the treatment and prevention of thrombus, platelet aggregation, atherosclerosis, restenosis, blood coagulation, hypertension, arrhythmia, angina pectoris, heart failure, inflammation and cancer when used alone or with other cardiovascular agents.

Synthesis and in vivo evaluation of 3,4-disubstituted gababutins

A range of 3,4-alkylated five-membered ring derivatives of gabapentin were synthesised. One compound (21) had an excellent level of potency against α2δ and was profiled in in vivo models of pain and anxiety.

POLYMORPHS OF A HYDROISOINDOLINE TACHYKININ RECEPTOR ANTAGONIST

This application is directed to a novel polymorph of a hydroisoindoline tachykinin receptor antagonist having the following structural formula A.

Process for making hydroisoindoline tachykinin receptor antagonists

The present invention is directed to a process for preparing certain hydroisoindoline compounds which are useful as neurokinin-1 (NK-1) receptor antagonists, and inhibitors of tachykinin and in particular substance P. The compounds are useful in the treatment of certain disorders, including emesis, urinary incontinence, depression, and anxiety.

Asymmetric cycloaddition routes to both enantiomers of trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid

Fumarates prepared from a series of optically active alcohols were used as dienophiles in Lewis acid catalyzed asymmetric cycloadditions to anthracene. The reactions gave high yields and d.e.'s of the diester cycloaddition products and acid hydrolysis could be performed under conditions yielding only about 10% racemization. The reactions form a valuable synthetic pathway to both enantiomers of the bicyclic dicarboxylic acid, since di-(-)-menthyl fumarate yielded the (-)-(S,S)-enantiomer and di-(+)-iso-menthyl fumarate the (+)-(R,R)-enantiomer of the acid. The other fumarates, obtained from (-)-borneol, (+)-fenchol and (-)-isopulegol, likewise gave the (-)-(S,S)-enantiomer of the acid. The absolute stereochemistry of the products was confirmed via a single crystal X-ray crystallographic structure determination of the brucine salt of the (-)-(S,S)-enantiomer.