148983-25-9

Basic information

• Product Name: Carbamic acid, [(2S)-2,3-dihydroxypropyl]-, 1,1-dimethylethyl ester (9CI)
• Synonyms: Carbamic acid, [(2S)-2,3-dihydroxypropyl]-, 1,1-dimethylethyl ester (9CI)
• CAS NO: 148983-25-9
• Molecular Formula: C₈H₁₇NO₄
• Molecular Weight: 191.22488
• Product Categories: N-BOC
• Mol File: 148983-25-9.mol

Chemical Properties

• Boiling Point: 361.6±32.0 °C(Predicted)
• Appearance: /
• Density: 1.136±0.06 g/cm3(Predicted)
• PKA: 12.19±0.46(Predicted)
• CAS DataBase Reference: Carbamic acid, [(2S)-2,3-dihydroxypropyl]-, 1,1-dimethylethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(2S)-2,3-dihydroxypropyl]-, 1,1-dimethylethyl ester (9CI)(148983-25-9)
• EPA Substance Registry System: Carbamic acid, [(2S)-2,3-dihydroxypropyl]-, 1,1-dimethylethyl ester (9CI)(148983-25-9)

Safety Data

• Hazardous Substances Data: 148983-25-9(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 148982-76-7 tert-butyl N-(2-oxiranylmethyl)carbamate 
• 61278-21-5 (S)-3-Amino-1,2-propanediol 

Relevant articles and documents

Diversity oriented concise asymmetric synthesis of azasugars: A facile access to l-2,3-trans-3,4-cis-dihydroxyproline and (3S,5S)-3,4,5-trihydroxypiperidine

Diversity oriented concise asymmetric syntheses of l-2,3-trans-3,4-cis-dihydroxyproline and (3S,5S)-3,4,5-trihydroxypiperidine have been developed from (R)-glycidol. The key step of the synthesis is Sharpless asymmetric dihydroxylation on enantiomerically pure TBDMS protected allylic alcohol 14 which generates the triol intermediate 15 in excellent de. The (2R,3R,4S)-2,3-dihydroxypentanoate derivative 15 was subsequently converted to natural pyrrolidine azasugar 1 and non-natural piperidine azasugar 4 under cascade reaction conditions in good yields.

MACROCYCLIC KINASE INHIBITORS AND THEIR USE

The present disclosure relates to certain chiral diaryl macrocyclic derivatives, pharmaceutical compositions containing them, and methods of using them to treat cancer, pain, neurological diseases, autoimmune diseases, and inflammation.

MACROCYCLIC COMPOUNDS FOR TREATING DISEASE

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Synthesis and Absolute Stereochemical Reassignment of Mukanadin F: A Study of Isomerization of Bromopyrrole Alkaloids with Implications on Marine Natural Product Isolation

Synthesis of both enantiomers of mukanadin F was achieved by using a seven step synthesis. Comparison of the optical rotation data of synthetic samples to that reported for the isolated natural product determined that the absolute configuration of the natural product is 9S and not the reported 9R. Further studies established that the reported low magnitude of optical rotation in the isolated sample is due to compounds of this type undergoing isomerization and racemization under benign laboratory conditions. Additionally the synthetic methods developed were applied to synthesize mukanadins B and D.

BIARYL MONOBACTAM COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF BACTERIAL INFECTIONS

The present invention relates to biaryl monobactam compounds of Formula I: and pharmaceutically acceptable salts thereof, wherein X, Y, Z, A1, Q, A2, M, W, RX and Rz are as defined herein. The present invention also relates to compositions which comprise a biaryl monobactam compound of the invention or a pharmaceutically acceptable salt therof, and a pharmaceutically acceptable carrier. The invention further relates to methods for treating a bacterial infection comprising administering to the patient a therapeutically effective amount of a compound of the invention, either alone or in combination with a therapeutically effective amount of a second beta-lactam antibiotic.

BRIDGED COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS

Novel bridged compounds are disclosed herein, along with their pharmaceutically acceptable salts, hydrates and prodrugs. Also disclosed are compositions comprising such compounds, methods of preparing such compounds and methods of using such compounds as antibacterial agents. The disclosed compounds, their pharmaceutically acceptable salts, hydrates and prodrugs, as well as compositions comprising such compounds, salts, hydrates and prodrugs, are useful for treating bacterial infections and associated diseases and conditions.

METALLO-BETA-LACTAMASE INHIBITORS

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Synthesis of homochiral tetrahydropteridines

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Transition state analogue inhibitors of human methylthioadenosine phosphorylase and bacterial methylthioadenosine/S-adenosylhomocysteine nucleosidase incorporating acyclic ribooxacarbenium ion mimics

Several acyclic hydroxy-methylthio-amines with 3-5 carbon atoms were prepared and coupled via a methylene link to 9-deazaadenine. The products were tested for inhibition against human MTAP and Escherichia coli and Neisseria meningitidis MTANs and gave Ki values as low as 0.23 nM. These results were compared to those obtained with 1st and 2nd generation inhibitors (1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-methylthio-d-ribitol (MT-Immucillin-A, 3) and (3R,4S)-1-[9-deazaadenin-9-yl)methyl]3-hydroxy-4- methylthiomethylpyrrolidine (MT-DADMe-Immucillin-A, 4). The best inhibitors were found to exhibit binding affinities of approximately 2- to 4-fold those of 3 but were significantly weaker than 4. Cleavage of the 2,3 carbon-carbon bond in MT-Immucillin-A (3) gave an acyclic product (79) with a 21,500 fold loss of activity against E. coli MTAN. In another case, N-methylation of a side chain secondary amine resulted in a 250-fold loss of activity against the same enzyme [(±)-65 vs (±)-68]. The inhibition results were also contrasted with those acyclic derivatives previously prepared as inhibitors for a related enzyme, purine nucleoside phosphorylase (PNP), where some inhibitors in the latter case were found to be more potent than their cyclic counterparts.

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