16854-32-3 Usage
Description
(1S,2S)-(+)-2-AMINO-1-[4-(METHYLTHIO)PHENYL]-1,3-PROPANEDIOL, also known as (1S,2S)-(+)-Thiomicamine, is an organic compound with a unique structure that features a chiral center and a methylthio group. It is characterized by its optical activity and is a valuable building block in the synthesis of various biologically active molecules.
Uses
(1S,2S)-(+)-Thiomicamine is used as a starting material in the synthesis of 3,4-dihydroisoquinolinium salts, which are employed as promoters in asymmetric epoxidation and oxidation reactions. These reactions are crucial in the production of enantiomerically pure compounds, which are essential in the pharmaceutical industry for the development of drugs with specific therapeutic effects.
Used in Pharmaceutical Industry:
(1S,2S)-(+)-Thiomicamine is used as a starting material in the synthesis of an α-amino acid named (3R,4R)-4-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid. This α-amino acid is used to prepare modified peptides of biological importance, which can have potential applications in the development of new drugs and therapies.
Used in Chiral Resolution:
(1S,2S)-(+)-Thiomicamine is used as a chiral base in the resolution of an angiotensin II type 2 receptor (AT2R) antagonist named EMA401. The resolution of chiral compounds is an important process in the pharmaceutical industry, as it allows for the separation of enantiomers with different biological activities, leading to more effective and safer drugs.
Check Digit Verification of cas no
The CAS Registry Mumber 16854-32-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,8,5 and 4 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 16854-32:
(7*1)+(6*6)+(5*8)+(4*5)+(3*4)+(2*3)+(1*2)=123
123 % 10 = 3
So 16854-32-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H15NO2S/c1-14-8-4-2-7(3-5-8)10(13)9(11)6-12/h2-5,9-10,12-13H,6,11H2,1H3/t9-,10-/m0/s1
16854-32-3Relevant articles and documents
Reversed-phase liquid chromatographic separation of enantiomeric and diastereomeric bases related to chloramphenicol and thiamphenicol.
Gal,Meyer-Lehnert
, p. 1062 - 1065 (2007/10/02)
The important antimicrobial agents chloramphenicol and thiamphenicol are N-acylated amines whose chemical structures include two chiral centers. Each drug is the single enantiomer of R,R configuration. The N-deacylated bases of the drugs are important intermediates in their synthesis and optical resolution. In this report, reversed-phase HPLC methods are described for the separation of enantiomeric and diastereomeric bases of the two drugs and of two closely related bases used in some syntheses of the drugs. The stereoisomeric bases were derivatized with a homochiral isothiocyanate and the resulting diastereomeric thioureas were separated on C18 columns with methanol:water mixtures as mobile phases and detection at 254 nm. The four stereoisomeric bases of chloramphenicol and those of its unnitrated analogue were thus separable after derivatization with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate. This reagent also allowed the separation of the D-threo isomer of the p-mercaptomethyl analogue of thiamphenicol base from its stereoisomers. The stereoisomers of thiamphenicol base were similarly separated with (R)-alpha-methylbenzyl isothiocyanate as the derivatizing agent. The diastereomers of chloramphenicol base and of thiamphenicol base were chromatographically separable after derivatization with the nonchiral reagent benzyl isothiocyanate. The procedures developed may be useful in the determination of the stereoisomeric composition of the drugs in research and in quality control, and may be applicable to other similar agents whose chemistry and pharmacology are receiving considerable attention.
