ChemicalBook CAS DataBase List n-Octyl-β-D-glucopyranoside

n-Octyl-β-D-glucopyranoside synthesis

11synthesis methods

Product Name:n-Octyl-β-D-glucopyranoside
CAS Number:29836-26-8
Molecular formula:C14H28O6
Molecular Weight:292.37

111-87-5 Synthesis

111-87-5
740 suppliers
$6.00/100g

50-99-7 Synthesis

50-99-7
995 suppliers
$6.00/25g

29836-26-8
319 suppliers
$16.80/1G

Yield:29836-26-8 15%

Reaction Conditions:

with Amberlite IR-120 (H⁺) resin for 0.133333 h;Microwave irradiation;

Steps:

5.2.1. Octyl b-D-glucopyranoside (2).

Amberlite IR-120 (H⁺) resin (2.0 g) was added to a solution of D-glucose (1.0 g, 5.551 mmol) in anhydrous 1-octanol (20 mL) and the mixture was placed in a domestic microwave oven. The mixture was irradiated 30 sec span for sixteen times (i.e. 8 min) at 180 watt when TLC indicated completion of reaction with the formation of a faster-moving product. The resin was filtered off and the filtrate concentrated under reduced pressure. The resulting syrup was purified by passage through a silica gel column (with ethyl acetate/methanol, 8/1, v/v as eluant) to give the desired glycoside 2. However, some octanol (bp ~195 °C) was present with glucoside 2, which took our tedious effort (heating at 90-100 °C) to remove octanol and we obtained a little amount of compound 2 (0.244 g, 15%) as a solid. Recrystallization from absolute ethanol gave the glucoside 2 as needles, mp 101-103 °C, lit. [22] mp 97-103 °C. R_f = 0.51 (ethyl acetate/methanol = 2/1, v/v); FT-IR (KBr): ν 3200-3560 (OH), 1080 cm^-1(pyranose ring); ¹H NMR (400 MHz, CDCl₃): d_H 4.32 (d, 1H, J_1,2 7.8 Hz, H-1), 3.78-3.91 [br m, 7H, H-6, CH₃(CH₂)₆CH_AH_BO and 4×OH], 3.63 (t, 1H, J_2,3;3,4 = 9.2 Hz, H-3), 3.50-3.57 [m, 2H, H-5 and CH₃(CH₂)₆CH_AH_BO], 3.39 (dd, 1H, H-2), 3.32 (t, 1H, J_4,5 9.3 Hz, H-4), 1.61-1.68 [m, 2H, CH₃(CH₂)₅CH₂CH₂O], 1.22-1.37 [m, 10H, CH₃(CH₂)₅CH₂CH₂O], 0.90 [t, 3H, J 6.6 Hz, CH₃(CH₂)₇O]; ¹³C NMR (100 MHz, CDCl₃): d_C 102.8 (C-1), 76.4 (C-3), 75.5 (C-2), 73.4 (C-5), 70.6 [CH₃(CH₂)₆CH₂O], 69.5 (C-4), 61.4 (C-6), 31.8, 29.6, 29.5, 29.3, 25.9, 22.7 [CH₃(CH₂)₆CH₂O], 14.1 [CH₃(CH₂)₇O]; Anal. Calcd for C₁₄H₂₈O₆: C, 57.51; H, 9.65. Found: C, 57.62; H, 9.63.

References:

Matin, Mohammed M.;Bhattacharjee, Sreebash C.;Chakraborty, Priyanka;Alam, Muhammad S. [Carbohydrate Research,2019,vol. 485,art. no. 107812] Location in patent:supporting information

38954-67-5 Synthesis