Activation of glycoyl trihaloacetimidates with acid-washed molecular sieves in the glycosidation reaction

Organic Letters

Volumn 5, Issue 7, 2003, Pages 987-989

  Adinolfi, Matteo ^a   Barone, Gaspare ^a   Iadonisi, Alfonso ^a   Schiattarella, Marialuisa ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; SACCHARIC ACID; ACID; GLYCOSIDE;

ARTICLE; CHEMICAL REACTION; GLYCOSIDATION; MOLECULAR BIOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE; RECYCLING; STEREOCHEMISTRY; CHEMICAL STRUCTURE; CHEMISTRY; GLYCOSYLATION;

ACIDS; GLYCOSIDES; GLYCOSYLATION; MOLECULAR STRUCTURE;

EID: 0041728885     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027353i     Document Type: Article

References (15)

1. Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-124.
2. Yu, B.; Tao, H. Tetrahedron Lett. 2001, 42, 2405-2407.
3. Adinolfi, M.; Barone, G.; Iadonisi, A.; Schiattarella, M. Synlett 2002, 269-270.
4. Adinolfi, M.; Barone, G.; Iadonisi, A.; Schiattarella, M. Tetrahedron Lett. 2002, 43, 5573-5577.
5. Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L.; Schiattarella, M. Tetrahedron Lett. 2001, 42, 5967-5969.
6. Fraser Reid, B.; Udodong, U. E.; Wu, Z.; Ottesson, H.; Merritt, J. R.; Rao, C. S.; Roberts, C.; Madsen, R. Synlett 1992, 927-942.
7. Nakajima, N.; Saito, M.; Kudo, M.; Ubukata, M. Tetrahedron 2002, 58, 3579-3588.
8. Demchenko, A.; Stauch, T.; Boons, G.-J. Synlett 1997, 818-821.
9. Schmidt, R. R.; Behrendt, M. M.; Toepfer, M. W. Synlett 1990, 694-696.
10. Reactive furanosyl chloride donors can be activated by ordinary molecular sieves: (a) Zissis, C.; Glaudemans, C. P. J. Carbohydr. Res. 1976, 50, 292-294. (b) Nilsson, S.; Bengtsson, M.; Norberg, T. J. Carbohydr. Chem. 1992, 11, 265-285.
11. Reactive furanosyl chloride donors can be activated by ordinary molecular sieves: (a) Zissis, C.; Glaudemans, C. P. J. Carbohydr. Res. 1976, 50, 292-294. (b) Nilsson, S.; Bengtsson, M.; Norberg, T. J. Carbohydr. Chem. 1992, 11, 265-285.
12. For applications of zeolites in organic synthesis see: Holderich, W.; Hesse, M.; Naumann, F. Angew. Chem., Int. Ed. Engl. 1988, 27, 226-241.
13. For recent examples in the use of solid acids as recoverable activators of armed sulfoxide donors see: (a) Nagai, H.; Matsumura, S.; Toshima, K. Tetrahedron Lett. 2000, 41, 10233-10237. (b) Nagai, H.; Kawahara, K.; Matsumura, S.; Toshima, K. Tetrahedron Lett. 2001, 42, 4159-4162.
14. For recent examples in the use of solid acids as recoverable activators of armed sulfoxide donors see: (a) Nagai, H.; Matsumura, S.; Toshima, K. Tetrahedron Lett. 2000, 41, 10233-10237. (b) Nagai, H.; Kawahara, K.; Matsumura, S.; Toshima, K. Tetrahedron Lett. 2001, 42, 4159-4162.
15. Typical procedure: donor 1 (23.0 mg, 0.042 mmol) and acceptor 5 (12.1 mg, 0.032 mmol) were dissolved under argon in toluene (1 mL) in the presence of freshly activated acid-washed 4 Å molecular sieves AW MS 300 (600 rag, purchased from Fluka, 1/8 in. rods). After being stirred for 30 min at room temperature, the mixture was heated at 70°C for 2 h, and then a few drops of triethylamine was added. The mixture was filtered and concentrated and the residue chromatographed on a short silica gel column eluted with 7:3 hexane/ethyl acetate to afford disaccharide 10 (21.7 mg, yield 91%). The procedure was upscaled for the synthesis of 19: acceptor 17 (228 mg, 0.48 mmol) and donor 18 (426 mg, 0.62 mmol) were azeotroped three times with anhydrous toluene. The mixture was then dissolved at 0°C (ice bath) under argon in anhydrous dichloroethane (10 mL) in the presence of 4 Å AW 300 MS (2.4 g). After 30 min the ice bath was removed, and the mixture was left under stirring for 24 h at room temperature. An additional aliquot of AW MS (2.4 g) was then added. After a further 24 h, a few drops of triethylamine was added and the mixture was filtered and concentrated. Silica gel chromatography of the residue (eluent 85:15 hexane-AcOEt) yielded 312 mg (68%) of disaccharide 19. The recovered sieves were dehydrated and reactivated by overnight heating at 200°C under vacuum.