91796-57-5

Basic information

• Product Name: (1S,2R,5S)-(+)-MENTHYL (R)-P-TOLUENESULFINATE
• Synonyms: (1S,2R,5S)-(+)-MENTHYL (R)-P-TOLUENESULFINATE;(1S,2R,5S)-MENTHYL (R)-P-TOLUENESULFINATE;(+)-(1S)-MENTHYL (R)-TOLUENE-4-SULFINATE;(R)-(+)-MENTHYL P-TOLUENESULFINATE;(R)-(+)-P-TOLUENESULFINIC ACID D-MENTHYL ESTER;(+)-(1S)-Menthyl (R)-p-toluenesulfinate;p-Toluenesulfinic acid (1R)-5β-methyl-2β-isopropylcyclohexan-1β-yl ester;Benzenesulfinic acid, 4-Methyl-,(1S,2R,5S)-5-Methyl-2-(1-Methylethyl)cyclohexylester, [S(R)]-
• CAS NO: 91796-57-5
• Molecular Formula: C₁₇H₂₆O₂S
• Molecular Weight: 294.45
• Product Categories: chiral;Asymmetric Synthesis;Biochemistry;Monocyclic Monoterpenes;Synthetic Organic Chemistry;Terpenes
• Mol File: 91796-57-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 104-106 °C(lit.)
• Appearance: /
• Refractive Index: 200 ° (C=2, Acetone)
• Storage Temp.: −20°C
• BRN: 4907352
• CAS DataBase Reference: (1S,2R,5S)-(+)-MENTHYL (R)-P-TOLUENESULFINATE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R,5S)-(+)-MENTHYL (R)-P-TOLUENESULFINATE(91796-57-5)
• EPA Substance Registry System: (1S,2R,5S)-(+)-MENTHYL (R)-P-TOLUENESULFINATE(91796-57-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 91796-57-5(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 91796-57-5 differently. You can refer to the following data:
1. (1S,2R,5S)-(+)-Menthyl (R)-p-Toluenesulfinate is used as a reactant in the stereoselective synthesis of pyrazole derivatives using tert-butansulfonamide as a chiral auxiliary.
2. (1S,2R,5S)-(+)-Menthyl (R)-p-toluenesulfinate can be used:As a chiral electrophile in the synthesis of fluorescent triazolopyridine ligands.To prepare various sulfinimines, which are further used in the synthesis of α-aminophosphonic acids by reacting with borane complexes.In one of the key synthetic steps for the synthesis of (S)-(+)-ethyl β-amino-3-pyridinepropanoate, a component of an antiplatelet agent.

InChI:InChI=1/C17H26O2S/c1-12(2)16-10-7-14(4)11-17(16)19-20(18)15-8-5-13(3)6-9-15/h5-6,8-9,12,14,16-17H,7,10-11H2,1-4H3/t14-,16?,17?,20?/m0/s1

Upstream product

• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 103-19-5 di(p-tolyl) disulfide 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 89-78-1 menthol 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 343257-00-1 (S)-2-Benzyl-3,3,3-trifluoro-2-((R)-toluene-4-sulfinylamino)-propionic acid methyl ester 
• 6873-90-1 N-benzyl-4-methylbenzenesulfinamide 
• 2216-51-5 (-)-menthol 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 100-51-6 benzyl alcohol 
• 15356-70-4 menthol 
• 536-57-2 p-toluene sulfinic acid 
• 672-78-6 methyl p-toluene sulfinate 
• 334023-36-8 N-(p-tolylsulfinylimino)triphenylphosphorane 

Downstream Products

• 124770-15-6 6-(1-hydroxycyclohexyl)-2-p-tolylsulphinylcyclohexanone 
• 83859-24-9 (2R,R_S)-2-p-tolylsulphinylcyclohexanone 
• 83859-17-0 (S₂,R_S)-2-p-Tolylsulfinylcyclohexanone 
• 104871-67-2 (R)-2-(p-tolylsulfinyl)-1-cyclohexanone 
• 86000-96-6 1-((S)-4-Methoxymethyl-cyclohexylmethanesulfinyl)-4-methyl-benzene 
• 94110-80-2 1-Methyl-4-((S)-4-pentyl-cyclohexylmethanesulfinyl)-benzene 
• 131154-12-6 4-Methyl-benzenesulfinic acid [1-phenyl-pent-(E)-ylidene]-amide 
• 188447-75-8 4-Methyl-benzenesulfinic acid [1-phenyl-eth-(E)-ylidene]-amide 
• 61187-71-1 (+)-(R)-(dimethoxyphosphoryl)methyl p-tolyl sulfoxide 
• 175689-22-2 (R)-(-)-N-(3-pyridinemethylidene)-p-toluenesulfinamide 
• 188709-37-7 tert-butyl (-)-(S_S)-3-oxo-4-p-tolylsulfinyl-butanoate 
• 218168-22-0 methyl (-)-(S)-3,5-dioxo-6-(p-tolylsulfinyl)hexanoate 
• 302934-11-8 (S)-2-(Triisopropylsyloxymethyl)phenyl p-tolylsulfoxide 
• 1519-39-7 (R)-methyl p-tolyl sulfoxide 

Relevant articles and documents

Sodium Arenesulfinates-Involved Sulfinate Synthesis Revisited: Improved Synthesis and Revised Reaction Mechanism

Reaction of alcohols with sodium arenesulfinates could afford either sulfones or sulfinates, and O-attack of sulfinate anions onto the in situ generated carbocation intermediates from alcohols was the previous proposed reaction mechanism in many syntheses of sulfinates. This concept, which is often used consciously or unconsciously, was revised herein by using isotopic labeling experiments and development of an improved sulfinate synthesis. The improved sulfinate synthetic protocol possesses many advantages such as a high sulfinate/sulfone selectivity, a broad substrate scope, metal-free, and mild reaction conditions. The revised reaction mechanism necessitates revision of many previous proposed reaction mechanisms in literatures.

Highly diastereoselective synthesis and easy method for synthesis of optically active sulfinate esters from aromatic disulfides

One-step synthesis of chiral aromatic sulfinate esters 2 from aromatic disulfides 1 using lead tetraacetate is reported. The yields are good to excellent and diastereoselectivity is high.

Synthesis of Optically Active α-Alkylidene-β-hydroxy-γ-methylenebutyrolactones. Isoobtusilactones and Isomahubalactones (Isomahubanolide and Isomahubenolide)

The title compounds were prepared via stereoselective aldol reaction of α,β-unsaturated carboxylate α-anion equivalent, derived from optically active α-(arylsulfinyl)carboxylate and bromomagnesium diisopropylamide, with propargyl aldehyde as a key step.