Rapid Oligosaccharide Synthesis on a Novel Benzyl-Type Fluorous Support

Kohtaro Goto; Tsuyoshi Miura; Mamoru Mizuno; Hiromi Takaki; Nobuyuki Imai; Yasuoki Murakami; Toshiyuki Inazu

doi:10.1055/s-2004-831323

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Synlett 2004(12): 2221-2223
DOI: 10.1055/s-2004-831323

LETTER

Rapid Oligosaccharide Synthesis on a Novel Benzyl-Type Fluorous Support

Kohtaro Goto^a, Tsuyoshi Miura*^a,b, Mamoru Mizuno^a, Hiromi Takaki^a, Nobuyuki Imai^b, Yasuoki Murakami^b, Toshiyuki Inazu*^a,c
^a The Noguchi Institute, 1-8-1 Kaga, Itabashi-ku, Tokyo 173-0003, Japan
^b Faculty of Pharmaceutical Sciences, Chiba Institute of Science, 3 Shiomi-cho, Choshi, Chiba 288-0025, Japan
^c Department of Applied Chemistry, School of Engineering, and Institute of Glycotechnology, Tokai University, Kitakaname 1117, Hiratsuka, Kanagawa 259-1292, Japan
e-Mail: tmiura@cis.ac.jp;

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Publication History

Received 24 June 2004
Publication Date:
31 August 2004 (online)

Abstract
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Abstract

A novel benzyl-type fluorous support (HfBn-OH) has been easily prepared, and the HfBn group was successfully introduced to the anomeric position of the carbohydrate, then removed in high yield after working as a support. The use of the HfBn group made it possible to synthesize an oligosaccharide with minimal column chromatography purification. It was found that each HfBn derivative as a synthetic intermediate is easily purified only by fluorous-organic solvent extraction.

Key words

fluorous - oligosaccharide - support - rapid synthesis

References

1 Horváth IT. Rábai J. Science 1994, 266: 72

Crossref Google Scholar
2a Hao H. Yamazaki O. Yoshida A. Nishikido J. Tetrahedron Lett. 2003, 44: 4977

Crossref Google Scholar
2b Tzschucke CC. Markert C. Bannwarth W. Roller S. Hebel A. Haag R. Angew. Chem. Int. Ed. 2002, 41: 3964

Crossref Google Scholar
2c Nishikido J. Kamishima M. Matsuzawa H. Mikami K. Tetrahedron 2002, 58: 8345

Crossref Google Scholar
2d Rocaboy C. Gladysz JA. Org. Lett. 2002, 4: 1993

Crossref Google Scholar
2e Nakamura Y. Takeuchi S. Okumura K. Ohga Y. Tetrahedron 2001, 57: 5565

Crossref Google Scholar
2f Barrett AGM. Braddock DC. Catterick D. Chadwick D. Henschke JP. McKinnell RM. Synlett 2000, 847

Crossref Google Scholar
2g Horváth IT. Acc. Chem. Res. 1998, 31: 641 ; and references cited therein

Crossref Google Scholar
3a Curran DP. Pure Appl. Chem. 2000, 72: 1649

Crossref PubMed Google Scholar
3b Curran DP. Angew. Chem. Int. Ed. 1998, 37: 1174

Crossref PubMed Google Scholar
3c Zhang Q. Luo Z. Curran DP. J. Org. Chem. 2000, 65: 8866

Crossref PubMed Google Scholar
3d Zhang W. Luo Z. Chen CH. Curran DP. J. Am. Chem. Soc. 2002, 124: 10443

Crossref PubMed Google Scholar
3e Curran DP. Furukawa T. Org. Lett. 2002, 4: 2233

Crossref PubMed Google Scholar
3f Zhang Q. Rivkin A. Curran DP. J. Am. Chem. Soc. 2002, 124: 5774

Crossref PubMed Google Scholar
3g Curran DP. Synlett 2001, 1488

Crossref PubMed Google Scholar
3h Luo Z. Zhang Q. Oderaotoshi Y. Curran DP. Science 2001, 291: 1766

Crossref PubMed Google Scholar
4a Curran DP. Amatore M. Guthrie D. Campbell M. Go E. Luo Z. J. Org. Chem. 2003, 68: 4643

Crossref Google Scholar
4b Roger W. Zhang C. Tetrahedron Lett. 2003, 44: 7045

Crossref Google Scholar
4c Schwinn D. Bannwarth W. Helv. Chim. Acta 2002, 85: 255

Crossref Google Scholar
4d Filippov DV. Zoelen DJ. Oldfield SP. Marel GA. Overkleeft HS. Drijfhout JW. Boom JH. Tetrahedron Lett. 2002, 43: 7809

Crossref Google Scholar
4e Pardo J. Cobas A. Guitlán E. Castedo L. Org. Lett. 2001, 3: 3711

Crossref Google Scholar
4f Luo Z. Williams J. Read RW. Curran DP. J. Org. Chem. 2001, 66: 4261

Crossref Google Scholar
4g Wipf P. Reeves JT. Balachandran R. Giuliano KA. Hamel E. Day BW. J. Am. Chem. Soc. 2000, 122: 9391

Crossref Google Scholar
4h Röver S. Wipf P. Tetrahedron Lett. 1999, 40: 5667

Crossref Google Scholar
4i Wipf P. Reeves JT. Tetrahedron Lett. 1999, 40: 5139

Crossref Google Scholar
4j Wipf P. Reeves JT. Tetrahedron Lett. 1999, 40: 4649

Crossref Google Scholar
4k Curran DP. Ferritto R. Hua Y. Tetrahedron Lett. 1998, 39: 4937

Crossref Google Scholar
4l Studer A. Curran DP. Tetrahedron 1997, 53: 6681

Crossref Google Scholar
4m Manzoni L. Chem. Commun. 2003, 2930

Crossref Google Scholar
5a Miura T. Inazu T. Tetrahedron Lett. 2003, 44: 1819

Crossref Google Scholar
5b Miura T. Hirose Y. Ohmae M. Inazu T. Org. Lett. 2001, 3: 3947

Crossref Google Scholar
5c Miura T. Goto K. Waragai H. Matsumoto H. Hirose Y. Ohmae M. Ishida H.-K. Satoh A. Inazu T. J. Org. Chem. 2004, 69: 5348

Crossref Google Scholar
6 Miura T. Goto K. Hosaka D. Inazu T. Angew. Chem. Int. Ed. 2003, 42: 2047

Crossref PubMed Google Scholar
7a Mizuno M. Goto K. Miura T. Hosaka D. Inazu T. Chem. Commun. 2003, 972

Crossref Google Scholar
7b Mizuno M. Goto K. Miura T. Matsuura D. Inazu T. Tetrahedron Lett. 2004, 45: 3425

Crossref Google Scholar
10a Bock K. Pedersen C. Pedersen H. Adv. Carbohydr. Chem. Biochem. 1983, 42: 193

Crossref Google Scholar
10b Ajisaka K. Fujimoto H. Nishida H. Carbohydr. Res. 1988, 180: 35

Crossref Google Scholar

8

Compound 5: ¹H NMR (CDCl₃): δ = 1.73-1.95 (m, 8 H), 1.95-2.17 (m, 8 H), 2.39-2.82 (m, 16 H), 3.23-3.79 (m, 25 H), 4.68 and 4.70 (each s, 2 H, split of HO-CH ₂-Ph), 7.21-7.42 (m, 6 H). MALDI-TOF-MS: m/z calcd for C₉₀H₆₆F₁₀₂N₇O₈ [M + H⁺]: 3310.3. Found: 3310.4.

9

Compound 5 was obtained by treatment with sodium methoxide after coupling, because a slight excess amount of 4 further reacted with the hydroxyl function of 5 to give the undesired ester.

11

The fluorocarbon solvent (EtOC₄F₉, Novec^TM HFE-7200) is commercially available.

12

The fluorocarbon solvent (FC-72, bp 76 °C, formally called Fluorinert^TM FC-72) is commercially available and consists of perfluorohexane isomers (C₆F₁₄).