Syntheses of Glucosides. I

Abstract

Berger and Bradley synthesized a large number of glycerol ethers of which 3-(2' methylphenoxy) propane-1, 2-dzol has been used as myostatie anesthetic under the trade name of Myanesin.

Contribution of Several Volatile Phenols and Their Glycoconjugates to Smoke-Related Sensory Properties of Red Wine

“…The flask was cooled on ice, and methanol (20 mL) was added; the mixture was stirred for a further 30 min before being concentrated under reduced pressure. The resulting oil was purified by silica column chromatography (CH 2 Cl 2 →10% Et 2 O/CH 2 Cl 2 ; R f = 0.59 in 10% Et 2 O/CH 2 Cl 2 ) and recrystallized from EtOH to give a 21 3-Methylphenyl 1-O-β-D-Glucopyranoside (m-Cresol β-D-Glucoside). m-Cresol tetra-O-acetylglucoside (451 mg, 1.0 mmol) was stirred overnight at room temperature in methanol/water/ triethylamine (8:1:1 v/v, 9 mL).…”

“…This procedure was repeated several times until the solid residue reached a constant weight. The solid was recrystallized from ethanol to give a white powder (192 mg, 69%; R f = 0.41 in CH 2 Cl 2 /CH 3 OH/CH 3 COOH 79.5:20:0.5 v/v), which was >99% pure by HPLC-DAD at 280 nm: 1 H NMR (CD 3 OD), δ7.14 (1H, t, J = 7.8 Hz, H 5 ), 6.92 (1H, s, H 2 ), 6.86 (1H, dd, J = 7.8, 2.3 Hz, H 6 ), 6.80 (1H, d, J = 7.8 Hz, H 4 ), 4.88 (1H, d, J = 7.5 Hz, H 1′ ), 3.86 (1H, dd, J = 12.2, 2.5 Hz, H 6b′ ), 3.67 (1H, dd, J = 12.2, 5.5 Hz, H 6a′ ), 3.47 (1H, dd, J = 9.1, 8.9 Hz, H 3′ ), 3.46 (1H, dd, J = 9.1, 7.5 Hz, H 2′ ), 3.43 (1H, ddd, J = 10.1, 5.5, 2.5 Hz, H 5′ ), 3.39 (1H, t, J = 8.9 Hz, H 4′ ), 2.31 (s, 3H, H 7 ); 13 21 Chemical Analysis. The basic chemical composition of all wines was determined by the AWRI Commercial Services as detailed in Iland et al 22 The titratable acidity, volatile acidity, and alcohol were measured using FTIR WineScan (FOSS, Hillerød, Denmark).…”

“…The solid was recrystallized from ethanol to give a white powder (192 mg, 69%; R f = 0.41 in CH 2 Cl 2 /CH 3 OH/CH 3 COOH 79.5:20:0.5 v/v), which was >99% pure by HPLC-DAD at 280 nm: 1 H NMR (CD 3 OD), δ7.14 (1H, t, J = 7.8 Hz, H 5 ), 6.92 (1H, s, H 2 ), 6.86 (1H, dd, J = 7.8, 2.3 Hz, H 6 ), 6.80 (1H, d, J = 7.8 Hz, H 4 ), 4.88 (1H, d, J = 7.5 Hz, H 1′ ), 3.86 (1H, dd, J = 12.2, 2.5 Hz, H 6b′ ), 3.67 (1H, dd, J = 12.2, 5.5 Hz, H 6a′ ), 3.47 (1H, dd, J = 9.1, 8.9 Hz, H 3′ ), 3.46 (1H, dd, J = 9.1, 7.5 Hz, H 2′ ), 3.43 (1H, ddd, J = 10.1, 5.5, 2.5 Hz, H 5′ ), 3.39 (1H, t, J = 8.9 Hz, H 4′ ), 2.31 (s, 3H, H 7 ); 13 C NMR (CD 3 OD), δ 159.12 (C 1 ), 140.53 (C 3 ), 130.14 (C 5 ), 124.08 (C 4 ), 118.41 (C 2 ), 114.66 (C 6 ), 102.26 (C 1′ ), 78.07 (C 5′ ), 77.94 (C 3′ ), 74.90 (C 2′ ), 71.36 (C 4′ ), 62.48 (C 6′ ), 21.52 (C 7 ); HR-MS calcd for C 13 H 18 NaO 6 + ([M + Na] + ) 293.1001, found 293.1005; [α] D , −64.1 ( c 0.5, H 2 O) [lit. −69.7 (H 2 O)]; mp 178–179 °C [lit. 183–184 °C] …”

BF3 ⋅ CH3CN Promotes a Formation of Aryl α‐O‐Glycosides from Pyranoses: A Facile Approach to Oligosaccharide EPS‐G7

“…The experimental details, characterization data, 1 H NMR and 13 C NMR copies for all the compounds are available in the supporting information for this paper. Additional references cited within the Supporting Information [16–28] …”

“…From 30 min to 4 h, the yield of α-anomer remained about 50 %, however, the yield of βanomer descended gradually (entries 14-17). As time prolonged, both isomers decreased (entries [18][19]. The acidic conditions caused the product to decompose and the βanomer isomerized to α-anomer simultaneously, thus resulted in the dominance of the α-anomer in the product.…”