Oxetanes

Oxetanes are close homologs of epoxides and are attractive modules for drug discovery. Rogers-Evans, Carreira, and co-workers have reported that replacing a gem-dimethyl unit with an oxetane unit demonstrated improved physio- and biochemical properties of a molecular scaffold. They also showed the use of 1,6-substituted azaspiro[3.3]heptanes containing an oxetane ring as alternatives to unstable 1,3-heteroatom substituted cyclohexanes. The oxetane ring can also function as a surrogate for a carbonyl group. In most cases, 3-oxetanone was the principal building block employed by the authors to install the oxetane unit.

The presence of the oxetane moiety in drug-like and biologically active molecules is nothing new to synthetic and medicinal chemists. Perhaps the best-known examples of oxetane-containing drugs are the natural product paclitaxel (Taxol®) and its synthetic analog docetaxel. Joëlle Dubois and co-workers studied the effect of the deletion of the oxetane ring in analogs of docetaxel and found the analogs to be less active than docetaxel in biological assays. Merrilactone A shows promise as a nonpeptidal neurotropic agent, and the β-amino acid oxetin has demonstrated both herbicidal and antibiotic activity.

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Oxetanes

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731536 3-Oxetanone C3H4O2
756962 3-Bromooxetane 95% C3H5BrO
731560 3-Iodooxetane 95% C3H5IO
84985 L-Serine β-lactone tetrafluoroborate salt ≥98.0% (T) C3H6NO2 · BF4
92459 Trimethylene oxide purum, ≥97.0% (GC) C3H6O
T76201 Trimethylene oxide 97% C3H6O
733296 3-Hydroxyoxetane 95% C3H6O2
777838 3-Aminooxetane 97% C3H7NO
CDS010703 3-oxetanamine AldrichCPR C3H7NO
CDS019474 3-Oxetanamine hydrochloride AldrichCPR C3H8ClNO
219126 β-Butyrolactone 98% C4H6O2
790591 Oxetane-3-carboxylic acid C4H6O3
745715 Oxetane-3-methanol 97% C4H8O2
745693 3-(Aminomethyl)oxetane 97% C4H9NO
759635 3-Amino-3-methyloxetane 97% C4H9NO
CDS008106 3-methyl-3-oxetanamine AldrichCPR C4H9NO
755923 N-Methyl-3-aminooxetane 97% C4H9NO
CDS019094 N-Methyl-3-oxetanamine AldrichCPR C4H9NO
340235 (R)-(+)-4-Methyl-4-(trichloromethyl)-2-oxetanone 98% C5H5Cl3O2
731579 2-(3-Oxetanylidene)acetonitrile 95% C5H5NO
CDS006155 3-Methyl-3-oxetanecarboxaldehyde AldrichCPR C5H8O2
745677 3-Methyloxetane-3-carboxylic acid 97% C5H8O3
CDS007824 3-bromomethyl-3-methyloxetane AldrichCPR C5H9BrO
192309 3,3-Dimethyloxetane 98% C5H10O
277681 3-Methyl-3-oxetanemethanol 98% C5H10O2
CDS019169 1-(3-Methyloxetan-3-yl)methanamine AldrichCPR C5H11NO
759643 2-Oxa-5-azaspiro[3.4]octane oxalate salt C6H11NO · xC2H2O4
L500534 2-Oxa-6-azaspiro[3.4]octane AldrichCPR C6H11NO
444197 3-Ethyl-3-oxetanemethanol 96% C6H12O2
731544 2-Oxa-7-azaspiro[3.5]nonane oxalate 97% C8H14NO3 · xC2H2O4
CVT00025 3-(Phenoxymethyl)-3-oxetanylamine AldrichCPR C10H13NO2
759651 1-Boc-6-oxa-1-azaspiro[3.3]heptane 95% (GC) C10H17NO3
CVT00028 3-[(4-Methoxyphenoxy)methyl]-3-oxetanamine AldrichCPR C11H15NO3
759694   6-Boc-2-oxa-6-azaspiro[3.4]octane 97% C11H19NO3
93470 N-Trityl-L-serine lactone ≥98.0% (sum of enantiomers, TLC) C22H19NO2