Preparation of monosaccharide having (mercaptomethyl)diacetylene compounds using solid-support as a thiol source

Synlett

Volumn , Issue 10, 2003, Pages 1395-1398

  Izumi, Minoru ^a   Shibakami, Motonari ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

Acetylenic coupling; Gold nanoparticle; Saccharide; Solid support; Thiol 2 chlorotrityl resin

Indexed keywords

(MERCAPTOMETHYL)DIACETYLENE; ACETYLENE DERIVATIVE; GOLD; MONOSACCHARIDE; NANOPARTICLE; RESIN; THIOL; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; SOLID; SYNTHESIS;

EID: 0042069865     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40853     Document Type: Article

References (16)

1. Izumi, M.; Takagi, T.; Shibakami, M. ITE Lett. Batteries 2002, 3, 707.
2. (a) Glaser, C. Ber. Dtsch. Chem. Ges. 1869, 2, 422.
3. (b) Glaser, C. Ann. Chem. Pharm. 1870, 154, 137.
4. (c) Montierth, J. M.; Demario, D. R.; Kurth, M. J.; Schore, N. E. Tetrahedron 1998, 54, 11741; this reference describes the polymer-supported Cadiot-Chodkiewicz coupling of acetylenes to provide unsymmetrical diynes.
5. (d) Siemsen, P.; Livingston, R.; Diederich, F. Angew. Chem. Int. Ed. 2000, 39, 2632; and references therein.
6. Commercially available from Novabiochem, an affiliate of Merck KGaA, Darmstadt, Germany.
7. 2O, and MeOH to give 3.11 g of propargylated resin 3.
8. (a) Izumi, M.; Fukase, K.; Kusumoto, S. Biosci. Biotechnol. Biochem. 2002, 66, 211.
9. (b) Izumi, M.; Fukase, K.; Kusumoto, S. Synlett 2002, 1409.
10. 2O, and MeOH to give the resin having monosaccharide 6.
11. +.
12. A Procedure for Iodoalkynylation of Solid-support 3: The propargylated resin 3 (3.00 g, 1.44 mmol) was placed in a polypropylene tube fitted with a frit, and washed with DMF. Morpholine (2 mL), DMF (10 mL) and iodine (132 mg, 1.69 mmol) were added to the tube, successively. The reaction mixture was then shaken for 3 h. After the mixture was filtered, the resulting resin was washed with DMF and MeOH to give 3.31 g of 4.
13. 4 (16.6 mg, 0.01 mmol), DMF (2.5 mL), pyridine (2.5 mL) and 5 (132 mg, 0.43 mmol) were successively added to the tube. The reaction mixture was then vigorously stirred at r.t. After 24 h, the solution was removed by filtration and the resin washed with DMF and MeOH.
14. +.
15. 4 (39.3 mg, 0.10 mmol) was added 7 (32.9 mg, 0.10 mmol) in EtOH (3.0 mL) at 0 °C. The reaction mixture was then vigorously stirred. After stirring for 1 h, the gold nanoparticles that precipitated were obtained by centrifugation and then washed with MeOH. Removal of the residual solvent under reduced pressure afforded 11.5 mg of 14.
16. -1.