A facile H2SO4/4 Å molecular sieves catalyzed synthesis of 2,3-unsaturated O -glycosides via ferrier-type rearrangement

Synlett

Volumn , Issue 6, 2010, Pages 893-896

  Zhou, Jiafen ^a   Zhang, Bo ^a   Yang, Guofang ^a   Chen, Xuan ^a   Wang, Qingbing ^a   Wang, Zhongfu ^b   Zhang, Jianbo ^a   Tang, Jie ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b NORTHWEST UNIVERSITY   (China)

Author keywords

D glucal; Ferrier rearrangement; Glycosylation; Molecular sieves; O glycosides; Sulfuric acid

Indexed keywords

GLYCOSIDE; SULFURIC ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR SIZE; SYNTHESIS;

EID: 77949889654     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219539     Document Type: Article

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58. General Experimental Procedure Typically, H2SO4 (0.3 equiv, 16 ?L) was added to the mixture of D-glucal (1 mmol, 272 mg), 4 ? MS (272 mg) and alcohol (1.5 equiv) in CH2Cl2, and the reaction mixture was stirred for 5 min at r.t. After the reaction was completed, the reaction mixture was filtered and washed with CH2Cl2. The combined organic layer was washed with sat. NaHCO3 solution (10 mL) and sat. brine (10 mL), and then dried over anhyd Na2SO4. After evaporation of the solvent under reduced pressure, the crude products were purified by silica gel column chromatography (PE?EtOAc = 10:1). (34)
59. Selected Spectral Data n-Pentyl 4,6-Di-O-acetyl-2,3-dideoxy-a-D-erythro- hex-2- enopyranoside (5b) 1H NMR (500 MHz, CDCl3): δ= 0.91 (t, J = 6.7 Hz, 3 H), 1.34?1.37 (m, 4 H), 1.59?1.63 (m, 2 H), 2.07?2.10 (m, 6 H), 3.48?3.53 (m, 1 H), 3.75?3.80 (m, 1 H), 4.09?4.27 (m, 3 H, H-5, H-6a, H-6b), 5.03 (s, 1 H, H-1), 5.30?5.32 (dd, 1 H, J = 9.6 Hz, H-4), 5.83?5.89 (m, 2 H, H-2, H-3) ppm. 13C NMR (125 MHz, CDCl3): δ= 13.94, 20.69, 20.88, 22.40, 28.31, 29.32, 62.99, 65.27, 66.81, 68.87, 94.31, 127.92, 128.89, 170.22, 170.71 ppm. ESI-MS: m/z = 323.10 [M +Na+]. n-Decyl 4,6-Di-O-acetyl-2,3-dideoxy-a-D-erythro-hex-2- enopyranoside (6b) 1H NMR (500 MHz, CDCl3): δ= 0.86 (t, 3 H), 1.26?1.35 (m, 16 H), 2.07?2.09 (m, J = 9.2 Hz, 6 H), 3.49 (m, 1 H), 4.09? 4.26 (m, 3 H, H-5, H-6a, H-6b), 5.01 (s, 1 H, H-1), 5.29?5.32 (dd, J = 1.3, 9.7 Hz, 1 H, H-4), 5.83?5.88 (m, 2 H, H-2, H- 3) ppm. 13C NMR (125 MHz, CDCl3): δ= 14.00, 20.69, 20.87, 22.58, 25.67, 26.16, 29.23, 29.36, 29.47, 31.81, 32.70, 62.92, 64.37, 66.80, 68.94, 94.32, 127.90, 128.88, 170.27, 170.76 ppm. ESI-MS: m/z = 393.20 [M + Na+] 2-Ethylhexyl 4,6-Di-O-acetyl-2,3-dideoxy-a-D-erythrohex- 2-enopyranoside (12b) 1H NMR (500 MHz, CDCl3): δ= 0.86?0.91 (m, 6 H), 1.26? 1.33 (m, 8 H), 1.34?1.42 (m, 1 H), 2.09?2.10 (m, J = 5.7 Hz, 6 H), 3.36?3.38 (q, 1 H), 3.54?3.55 (d, 1 H), 3.70?3.71 (t, 1 H), 4.08?4.25 (m, 3 H, H-5, H-6a, H-6b), 5.00 (s, 1 H, H-1), 5.29?5.31 (dd, J = 9.7 Hz, 1 H, H-4), 5.82?5.94 (m, 2 H, H-2, H-3) ppm. 13C NMR (125 MHz, CDCl3): δ= 11.02, 13.99, 20.67, 20.87, 22.94, 23.68, 28.93, 30.49, 39.57, 63.03, 65.28, 66.87, 72.64, 94.45-94.53, 127.95, 128.74, 170.21, 170.71 ppm. ESI-MS: m/z = 365.14 [M + Na+]. 2-yanoethyl 4,6-Di-O-acetyl-2,3-dideoxy-a-D-erythrohex- 2-enopyranoside (15b) 1H NMR (500 MHz, CDCl3): δ= 2.08?2.10 (m, J = 10.0 Hz, 6 H), 2.64?2.71 (m, 2 H), 3.76?3.97 (m, 2 H), 4.12?4.22 (m, 3 H, H-5, H-6a, H-6b), 5.07 (s, 1 H, H-1), 5.29?5.31 (dd, 1 H, J = 1.0, 9.5 Hz, H-4), 5.81?5.93 (m, 2 H, H-2, H-3) ppm. 13C NMR (125 MHz, CDCl3): δ= 18.96, 20.56, 20 72, 62.69, 63.26, 64.85, 67.14, 94.60, 117.58, 126.70, 129.57, 170.13, 170.59 ppm. ESI-MS: m/z = 306.07 [M + Na+]. Trichloroethyl 4,6-Di-O-acetyl-2,3-dideoxy-a-D- erythrohex- 2-enopyranoside (17b) 1H NMR (500 MHz, CDCl3): δ= 2.07?2.13 (m, J = 10.8 Hz, 6 H), 4.17?4.18 (d, 2 H), 4.27?4.36 (m, 3 H, H-5, H-6a, H- 6b), 5.31 (s, 1 H, H-1), 5.37?5.38 (dd, J = 9.2 Hz, 1 H, H-4), 5.97?6.00 (m, 2 H, H-2, H-3) ppm. 13C NMR (125 MHz, CDCl3): δ= 20.76, 20.87, 62.66, 65.01, 67.49, 76.15, 79.61, 96.37, 126.38, 130.20, 170.39, 170.92 ppm. ESI-MS: m/z = 382.94 [M + Na+].