New One-Carbon Degradative Transformation of β-Alkyl-β-azido Alcohols

Abstract

A new transformation of 2-azido-1-hydroxy-containing compounds to nitriles with one carbon less than the starting materials by oxidation was reported. The reaction can be performed under mild conditions.

Illuminating the binding interactions of galactonoamidines during the inhibition of β-galactosidase (E. coli)

“…17,18 After protection of the primary hydroxyl group at C-6 of 4 as triphenylmethyl ether yielding 5 (Scheme 2), 19,20 the hydroxyl group at C-2 was methylated affording 6 . 21 All temporary protecting groups of 6 were then removed with aqueous acetic acid affording 7 and, after perbenzylation, 8 .…”

“…17 Colorless oil; δ H (CDCl 3 ) 7.44 (dt, 8.0, 1.8, 2H), 7.13 (d, 7.8, 2H), 4.41 (d, 10.3, 1H), 4.18 (dd, 5.5, 2.3, 1H), 4.11 (dd, 7.0, 5.5, 1H), 3.98 (dd, 11.3, 7.0, 1H), 3.84 – 3.89 (m, 1H), 3.81 (dd, 11.5, 4.3, 1H), 3.55 (dd, 10.2, 6.9, 4H), 2.34 (s, 3H), 1.43 (s, 3H), 1.34 (s, 3H); δ C (CDCl 3 ) 138.2, 132.8, 129.7, 128.0, 110.3, 87.9, 79.2, 77.0, 73.8, 71.4, 62.4, 27.9, 26.3, 21.0; the spectral data of 4 match those previously reported. 38 …”

“…11,17 N -Bromosuccinimide (3.75 g, 21.1 mmol, 1.2 eqiv) was added to a solution of 8 (10.00 g, 17.5 mmol) in 100 mL acetone/H 2 O (9/1, v/v) at 0 °C. After 30 min, 20 mL of a saturated aqueous sodium bicarbonate solution were added.…”

Minor oxygenated cannabinoids from high potency Cannabis sativa L.

“…Comparison of the 13 C NMR spectrum of the oxidation product 9α-hydroxy-10-oxo-hexahydrocannabinol resulting from selective oxidation reaction of 9 S ,10 S -dihydroxy-hexahydrocannabinol (Cannabiripsol) with pyridinium chlorochromate (PCC), further supported the S configuration of C-9 where both have δ C at 73 (Fig. 2) (Fan et al, 2006). Thus compound 8 was established as 9α-hydroxy-10-oxo-Δ 6a,10a -THC.…”

Carbohydrate-conjugated 4-(1,3,2-dithiarsolan-2-yl)aniline as a cytotoxic agent against colorectal cancer

“…To synthesize the other reactant of the click reaction (i.e., azide 6), which bears the 1,3,4,6-tetra-Oacetyl-b-D-glucosamine (OADG) moiety, the amino group of commercially available 2-amino-2-deoxy-D-glucose (5) was converted to azido functionality by reaction with tri-uoromethanesulfonyl azide, followed by acetylation of its 1,3,4,6 hydroxyl groups to yield the key building block 6. 30,31 Coupling of 4 with 6 under typical conditions of click reaction produced the desired conjugate 8, which exists as a mixture of equilibrium of arsenic oxide 8a and its hydrated analog arsonous acid 8b. The presence of the arsenic oxide 8a and arsonous acid 8b was conrmed by NMR and mass spectrometry analysis.…”