79161-91-4

Basic information

• Product Name: 3-ThioMorpholinecarboxylic acid, Methyl ester, (R)-
• Synonyms: 3-ThioMorpholinecarboxylic acid, Methyl ester, (R)-
• CAS NO: 79161-91-4
• Molecular Formula: C6H9NO3S
• Molecular Weight: 175.20556
• Mol File: 79161-91-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-ThioMorpholinecarboxylic acid, Methyl ester, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ThioMorpholinecarboxylic acid, Methyl ester, (R)-(79161-91-4)
• EPA Substance Registry System: 3-ThioMorpholinecarboxylic acid, Methyl ester, (R)-(79161-91-4)

Safety Data

• Hazardous Substances Data: 79161-91-4(Hazardous Substances Data)

Upstream product

• 18598-63-5 L-cysteine methyl ester hydrochloride 
• 67-56-1 methanol 
• 114525-81-4 (R)-4-(tert-butoxycarbonyl)thiomorpholine-3-carboxylic acid 
• 1041173-31-2 1-vinyltetrahydro-1H-thiophenium trifluoromethanesulfonate 
• 872424-97-0 2-amino-3-(2-chloro-ethylsulfanyl)-propionic acid methyl ester hydrochloride 

Relevant articles and documents

Evaluation of synthetic FK506 analogues as ligands for the FK506-binding proteins 51 and 52

The FK506-binding proteins (FKBP) 51 and 52 are cochaperones that modulate the signal transduction of steroid hormone receptors. Both proteins have been implicated in prostate cancer. Furthermore, single nucleotide polymorphisms in the gene encoding FKBP51 have been associated with a variety of psychiatric disorders. Rapamycin and FK506 are two macrocyclic natural products that bind to these proteins indiscriminately but with nanomolar affinity. We here report the cocrystal structure of FKBP51 with a simplified α-ketoamide analogue derived from FK506 and the first structure-activity relationship analysis for FKBP51 and FKBP52 based on this compound. In particular, the tert-pentyl group of this ligand was systematically replaced by a cyclohexyl ring system, which more closely resembles the pyranose ring in the high-affinity ligands rapamycin and FK506. The interaction with FKBPs was found to be surprisingly tolerant to the stereochemistry of the attached cyclohexyl substituents. The molecular basis for this tolerance was elucidated by X-ray cocrystallography.

An annulation reaction for the synthesis of morpholines, thiomorpholines, and piperazines from β-heteroatom amino compounds and vinyl sulfonium salts

(Chemical Equation Presented) Heterocycling: Diphenyl vinyl sulfonium salt 1 acts first as an electrophile, then a base, and then again as an electrophile in this operationally simple, high yielding, one-pot synthesis of pharmacologically important morpholines, thiomorpholines, and piperazines. Compound 1 is an excellent synthon for the 1,2-ethane dication.

Convenient synthesis of 1,4-thiazane-3-carboxylic acid derivatives

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