66211-46-9

Usage

Chemical Properties

white to light yellow crystal powder

InChI:InChI=1/C3H9NO2/c4-1-3(6)2-5/h3,5-6H,1-2,4H2/t3-/m1/s1

Upstream product

• 131321-84-1 (R)-1-azido-2,3-dihydroxypropane 
• 122697-84-1 (2R,5R)-2-(tert-Butyl)-5-(hydroxymethyl)-1,3-oxazolidin-3-carbonsaeure-methylester 
• 60456-23-7 (S)-oxiranemethanol 
• 22195-47-7 4-aminomethyl-2,2-dimethyl[1,3]dioxolane 
• 616-30-8 3-Amino-1,2-propanediol 
• 910655-43-5 ethyl (2R,1'R)-2-acetyloxy-3-(1'-phenylethyl)aminopropionate 

Downstream Products

• 148983-23-7 (R)-1-<(tert-butoxycarbonyl)amino>-2,3-dihydroxypropane 
• 97859-49-9 (R)-5-(hydroxymethyl)-1,3-oxazolidin-2-one 
• 173465-37-7 [(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-carbamic acid tert-butyl ester 
• 799261-92-0 (R)-5-cyano-1-(2,3-dihydroxypropyl)-3-methyluracil 
• 869484-00-4 (R)-N-(2,3-dihydroxypropyl)-4-nitroaniline 
• 908256-15-5 7-((R)-2,3-hydroxypropylamino)-3-(2-trifluoromethoxyphenyl)-2H-isoquinolin-1-one 
• 718619-93-3 C₁₇H₁₆F₃IN₄O₄ 
• 641617-22-3 (R)-3-[N-(benzyloxycarbonyl)amino]-1,2-propanediol 
• 1020192-49-7 (R)-(2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl)methanol 
• 1089144-70-6 N-[(2R)-2,3-dihydroxypropyl]-2-methyl-5-[(Z)-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-4-phenyl-1H-pyrrole-3-carboxamide 
• 352524-57-3 (R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)oxazolidin-2-one 
• 955998-69-3 (R)-N-(2,3-dihydroxypropyl)stearamide 

Relevant academic research and scientific papers

HIV INTEGRASE INHIBITORS

The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

Synthesis and properties of crosslinked chiral nanoparticles via RAFT miniemulsion polymerization

Crosslinked chiral nanoparticles were successfully synthesized via reversible addition-fragmentation chain transfer (RAFT) miniemulsion polymerization of 6-O-p-vinylbenzyl-1,2:3,4di-O-isopropylidene-D-galactopyranose (VBPG) using linear poly(VBPG) as the macro-RAFT agent. The polymerization of VBPG in the absence of crosslinker was first studied and the kinetic results showed that the molecular weights of the obtained poly(VBPG) increased linearly with the monomer conversion and was in good consistency with the corresponding theoretical ones while there remained a relative narrow polydisperslty. The effect of the amount of crosslinker, divlnylbenzene, on the nanoparticle size and chiral separation properties of the obtained nanoparticles were investigated in detail using four racemates ±-3-Amino-1,2propanediol, D,L-arablnose, D,L-tartaric acid, and D,L-mandelic acid.

Ring opening of 2-acylaziridines by acid chlorides

Good nucleophilicity of the ring nitrogen in chiral (2R,1′R)-2-acyl-(1′-phenylethyl)aziridines initiated the reaction with various acid chlorides to form the corresponding acylaziridinium ion intermediates whose rings were opened by the chloride anion to

Efficient Pathways to (R)- and (S)-5-Hydroxymethyl-2-oxazolidinone and some Derivatives

2-Oxazolidinones are a very interesting class of compounds due to their various pharmacological effects.Two new syntheses of enantiomerically pure (R)- and (S)-5-hydroxymethyl-2-oxazolidinone have been developed starting with D-mannitol, L-ascorbic acid and (R)- or (S)-malic acid. (R)- and (S)-5-hydroxymethyl-2-oxazolidinone have been used to synthesize some new homochiral 2-oxazolidinone derivatives.

Syntheses of Novel Nucleoside Dimer Analogues Containing an Acyclic Nucleoside and a Carbamate Linkage

Novel acyclic nucleoside analogues 10 were synthesized and successfully incorporated into heterolytic nucleoside dimers 1-3 containing natural nucleosides and a carbamate linkage.

Synthesis and Structure-Activity Relationships of a Series of Penicillin-Derived HIV Proteinase Inhibitors: Heterocyclic Ring Systems Containing P'1 and P'2 Substituents

As an extension of our earlier work based upon a single penicillin-derived thiazolidine moiety we have found that the decahydroisoquinoline grouping, also present in Ro 31-8959, is an effective replacement for one of the thiazolidine units in C2 symmetric penicillin-derived dimers.Reaction of racemic epoxide 6 with -decahydro-N-(1,1-dimethylethyl)-3-isoquinolinecarboxamide gave diastereoisomers 34a and 34b.The stereochemistry of the hydroxyl grouping of 34a was determined to be (S).Reaction of the amines derived from 34a and 34b with thiazolidine 8a gave 50 and 51, respectively.Compound 50 was a potent inhibitor of HIV proteinase (IC50 = 23 nM) with antiviral activity against HIV-1 in vitro (EC50 C8166 cells = 50 nM).However, a poor pharmacokinetic profile in the dog for compound 50 and its analogues, in keeping with earlier studies on penicillin-derived dimers in three species, precluded their development as potential antivirals.

Enantioselective Synthesis of (2S)-1-Benzyloxy-2,3-propanediol and (2R)-1-amino-2,3-propanediol from Glycerol

Enantioselective syntheses of (2S)-1-benzyloxy- and (2R)-1-amino-2,3-propanediol from glycerol employing N,N-diisopropyl-10-camphorsulfonamide 1 as chiral auxiliary are described.

Substitution and Addition Reactions of Methyl (R)-2-tert-Butyl-Δ4-1,3-oxazoline-3-carboxylates

Enantiomerically pure Δ4-1,3-oxazolines (1-5) bearing a tert-butyl group in the position 2 are prepared on a 100-g scale from serine or threonine using an electrochemical key step.They contain highly reactive double bonds, amenable to stereoselective electrophilic (1-3) or nucleophilic attack (4, 5).Thus, Vilsmeier and Friedel-Crafts-type reactions (--> 21, 22) and Michael additions (--> 11, 13) occur at C-5.Furthermore, substituents may be introduced in position 4 (next to the carbamate group) by lithiation and reaction with electrophiles (products 4, 10).Finally, dienolate 16 (from 5) reacts with aldehydes at the exocyclic position (--> 18).Hydrogenations of the tri- or tetrasubstituted double bonds in the oxazolines thus obtained are highly stereoselective (--> 14, 19, 24, 26).In the most cases, the 2-tert-butyl substituent directs reactions to the opposite face of the five-membered ring.The overall transformations achieved are discussed with regard to the bonds of serine and threonine. - Key Words: EPC syntheses / Stereogenic centers, self-regeneration of / Δ4-1,3-Oxazoline, derivatives / Electrochemistry, oxidative decarboxylation (Hofer-Moest)