940890-90-4

Basic information

• Product Name: (S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE
• Synonyms: (S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE;1-Piperidinecarboxylic acid, 3-[(Methylsulfonyl)oxy]-, 1,1-diMethylethyl ester, (3S)-;1Piperidinecarboxylic acid, 3[(methylsulfonyl)oxy], 1,1dimeth;2-Methyl-2-propanyl (3S)-3-[(methylsulfonyl)oxy]-1-piperidinecarboxylate (S)tertButyl 3(methylsulfonyloxy)piperidine1carboxylate;(S)-1-Boc-3-mesyloxyl-piperidine
• CAS NO: 940890-90-4
• Molecular Formula: C₁₁H₂₁NO₅S
• Molecular Weight: 279.36
• Mol File: 940890-90-4.mol
• Article Data: 26

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE(940890-90-4)
• EPA Substance Registry System: (S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE(940890-90-4)

Safety Data

• Hazardous Substances Data: 940890-90-4(Hazardous Substances Data)

Usage

Description

(S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE, also known as tert-Butyl (3S)-3-[(Methylsulfonyl)oxy]piperidine-1-carboxylate, is a chemical compound with a unique structure that features a tert-butoxycarbonyl group, a piperidinyl group, and a methanesulfonyl group. (S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE plays a significant role in the synthesis of various pharmaceutical agents, particularly as a reactant in the production of non-nucleoside MtbTMPK inhibitors.

Uses

Used in Pharmaceutical Industry:
(S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE is used as a reactant in the synthesis of non-nucleoside MtbTMPK inhibitors for the development of novel antitubercular drugs. These inhibitors target the Mycobacterium tuberculosis thymidylate kinase enzyme (MtbTMPK), which is essential for the synthesis of thymidine monophosphate, a crucial component of DNA. By inhibiting MtbTMPK, these compounds can effectively combat tuberculosis, a significant global health concern.
In the synthesis process, (S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE serves as a key intermediate, contributing to the formation of the desired non-nucleoside MtbTMPK inhibitors. Its unique structure allows for the creation of various chemical bonds and interactions that are vital for the biological activity of the final product. As a result, this compound is an essential component in the ongoing research and development of new and effective treatments for tuberculosis.

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 143900-44-1 tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate 
• 101469-92-5 (S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 404577-34-0 (R)-3-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester 
• 14813-01-5 1-benzyl-3-hydroxypiperidine 
• 91599-79-0 (S)-1-N-benzyl-3-hydroxypiperidine 
• 91599-81-4 (R)-N-benzyl-3-hydroxypiperidine 
• 85275-45-2 N-tert-butoxycarbonyl-3-piperidinol 
• 75-75-2 methanesulfonic acid 

Downstream Products

• 85838-94-4 N-Boc-1,2,3,6-tetrahydropyridine 
• 946725-84-4 (R)-3-(3-fluoro-phenoxy)-piperidine 
• 946725-84-4 (S)-3-(3-fluoro-phenoxy)-piperidine 
• 902836-20-8 C₁₇H₂₅NO₃ 
• 912761-71-8 (R)-3-m-tolyloxy-piperidine 
• 1061682-78-7 (R)-tert-butyl 3-(dimethylamino)piperidine-1-carboxylate 
• 936563-87-0 ibrutinib 
• 143900-44-1 tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate 
• 404577-34-0 (R)-3-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester 
• 85275-46-3 tert-butyl (3R)-3-(p-tolylsulfonyloxy)piperidine-1-carboxylate 
• 143900-43-0 tert-butyl (3R)-3-hydroxypiperidine-1-carboxylate 
• 1022150-11-3 (3R)‐4‐amino‐3‐(4-phenoxyphenyl)‐1‐(1‐tert-butoxycarbonylpiperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine 
• 1553977-42-6 3-(4-phenoxyphenyl)-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3.4-d]pyrimidin-4-amine hydrochloride salt 

Relevant articles and documents

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Ibrutinib is an inhibitor of Bruton's tyrosine kinase that has been approved for the treatment of patients with chronic lymphocytic leukemia, mantle cell lymphoma and Waldenstrom's macroglobulinemia and is connected with toxicities. To minimize its toxicities, we linked ibrutinib to a cell-targeted, internalizing antibody. To this end, we synthesized a poly-anionic derivate, ibrutinib-Cy3.5, that retains full functionality. This anionic inhibitor is complexed by our anti-CD20-protamine targeting conjugate and free protamine, and thereby spontaneously assembles into an electrostatically stabilized vesicular nanocarrier. The complexation led to an accumulation of the drug driven by the CD20 antigen internalization to the intended cells and an amplification of its pharmacological effectivity. In vivo, we observed a significant enrichment of the drug in xenograft lymphoma tumors in immune-compromised mice and a significantly better response to lower doses compared to the original drug.

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