91796-57-5 Usage
Description
(1S,2R,5S)-(+)-MENTHYL (R)-P-TOLUENESULFINATE is a chiral reagent derived from menthol, a natural monoterpene alcohol found in peppermint oil. It possesses a unique stereochemistry with three chiral centers, which makes it a valuable building block in organic synthesis. Its sulfinate group allows for versatile reactivity and can be used in various chemical transformations.
Uses
Used in Pharmaceutical Industry:
(1S,2R,5S)-(+)-MENTHYL (R)-P-TOLUENESULFINATE is used as a chiral auxiliary in the stereoselective synthesis of pyrazole derivatives using tert-butansulfonamide. This chiral auxiliary helps to control the stereochemistry of the final product, which is crucial for the biological activity and selectivity of pharmaceutical compounds.
Used in Chemical Synthesis:
(1S,2R,5S)-(+)-MENTHYL (R)-P-TOLUENESULFINATE is used as a chiral electrophile in the synthesis of fluorescent triazolopyridine ligands. These ligands are important for the development of new sensors, imaging agents, and catalysts.
Used in Organic Chemistry:
(1S,2R,5S)-(+)-MENTHYL (R)-P-TOLUENESULFINATE can be used to prepare various sulfinimines, which are further used in the synthesis of α-aminophosphonic acids by reacting with borane complexes. These α-aminophosphonic acids are valuable building blocks in the synthesis of biologically active compounds, such as antibiotics and enzyme inhibitors.
Used in the Synthesis of Antiplatelet Agents:
(1S,2R,5S)-(+)-MENTHYL (R)-P-TOLUENESULFINATE is used in one of the key synthetic steps for the synthesis of (S)-(+)-ethyl β-amino-3-pyridinepropanoate, a component of an antiplatelet agent. This chiral reagent plays a crucial role in the enantioselective synthesis of the active pharmaceutical ingredient, ensuring the desired stereochemistry for optimal biological activity.
Check Digit Verification of cas no
The CAS Registry Mumber 91796-57-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,1,7,9 and 6 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 91796-57:
(7*9)+(6*1)+(5*7)+(4*9)+(3*6)+(2*5)+(1*7)=175
175 % 10 = 5
So 91796-57-5 is a valid CAS Registry Number.
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
91796-57-5Relevant articles and documents
Sodium Arenesulfinates-Involved Sulfinate Synthesis Revisited: Improved Synthesis and Revised Reaction Mechanism
Ji, Yuan-Zhao,Li, Hui-Jing,Zhang, Jin-Yu,Wu, Yan-Chao
, p. 1846 - 1855 (2019/02/14)
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
Hajipour,Islami
, p. 536 - 538 (2007/10/03)
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)
Nokami, Junzo,Ohtsuki, Hirotoshi,Sakamoto, Yasuhuko,Mitsuoka, Masayuki,Kunieda, Norio
, p. 1647 - 1650 (2007/10/02)
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.
