Title:
PROTECTING GROUPS USEFUL IN THE SYNTHESIS OF POLYSACCHARIDES, NATURAL PRODUCTS, AND COMBINATORIAL LIBRARIES
Document Type and Number:
WIPO Patent Application WO2001038337
Kind Code:
A3
Abstract:
One aspect of the present invention relates to optionally substituted halogenated benzyl halides and the like. These compounds are useful as halogenated benzyl ether-based protecting groups for a variety of functional groups. Another aspect of the present invention relates to use of said protecting groups in an orthogonal protecting group strategy for the synthesis of complex molecules that comprise a number of suitable functional groups. Another aspect of the present invention relates to saccharides bearing various arrays of protecting groups of the present invention. Another aspect of the present invention relates to a method of synthesizing an oligosaccharide or glycoconjugate, comprising the steps of: using a saccharide bearing at least one protecting group of the present invention to glycosylate a second molecule to give a product comprising said saccharide; and removing a protecting group of the present invention from said product.
Inventors:
BUCHWALD STEPHEN L
PLANTE OBADIAH J
SEEBERGER PETER H
PLANTE OBADIAH J
SEEBERGER PETER H
Application Number:
PCT/US2000/032050
Publication Date:
September 07, 2001
Filing Date:
November 21, 2000
Export Citation:
Assignee:
MASSACHUSETTS INST TECHNOLOGY (US)
International Classes:
C07B51/00; C07C25/02; C07H15/18; C07H15/203; C07H15/26; (IPC1-7): C07H15/18
Other References:
POHL N L ET AL: "Para-Chlorobenzyl Protecting Groups As Stabilizers of the Glycosidic Linkage: Synthesis of the 3'-O-Sulfated Lewis X Trisaccharide", TETRAHEDRON LETTERS,NL,ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, vol. 38, no. 40, 6 October 1997 (1997-10-06), pages 6985 - 6988, XP004090399, ISSN: 0040-4039
K. FUKASE ET AL.: "Novel oxidatively removable protecting groups and linkers for solid-phase synthesis of oligosaccharides", MOLECULAR DIVERSITY, vol. 2, 1996, pages 182 - 188, XP000998221
D. YAMASHIRO: "Protection of aspartic acid, serine, and threonine in solid-phase peptide synthesis", J. ORG. CHEM., vol. 42, 1977, pages 523 - 525, XP002164973
S. KOTO ET AL.: "Some 2,3,4,6-tetra-O-(p-chlorobenzyl)-alfa-D-hexopyranoses", CARBOHYDRATE RESEARCH, vol. 87, 1980, pages 294 - 296, XP002164974
A. PÜSCHL, J. KEHLER, O. DAHL: "Solution phase synthesis of dithymidine phosphorothioate by a phosphotriester method using new S-protecting groups", NUCLEOSIDES & NUCLEOTIDES, vol. 16, 1997, pages 145 - 158, XP002164975
J.T. KOVALAINEN ET AL.: "Synthesis and in vitro pharmacology of a series of new chiral histamine H3-receptor ligands: 2-(R and S)-amino-3-(1H-imidazol-4(5)-yl)propyl ether derivatives", J. MED. CHEM., vol. 42, 1999, pages 1193 - 1202, XP002164976
"Catalog Handbook of Fine Chemicals 1996-1997", ALDRICH, NEDERLAND, 1996, XP002164979
S. BUDAVARI (ED): "The Merck index", 1996, MERCK & CO, WHITEHOUSE STATION, NJ, XP002164980
S. BUDAVARI (ED): "The Merck index", 1996, MERCK & CO, WHITEHOUSE STATION, NJ, XP002164981
J.F. HARTWIG: "Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates: scope and mechanism", ANGEW. CHEM. INT. ED., vol. 37, 1998, pages 2047 - 2067, XP002164977
O.J. PLANTE, S.L. BUCHWALD, P.H. SEEBERGER: "Halobenzyl ethers as protecting groups for organic synthesis", J. AM. CHEM. SOC., vol. 122, 2000, pages 7148 - 7149, XP002164978
See also references of EP 1233970A2
K. FUKASE ET AL.: "Novel oxidatively removable protecting groups and linkers for solid-phase synthesis of oligosaccharides", MOLECULAR DIVERSITY, vol. 2, 1996, pages 182 - 188, XP000998221
D. YAMASHIRO: "Protection of aspartic acid, serine, and threonine in solid-phase peptide synthesis", J. ORG. CHEM., vol. 42, 1977, pages 523 - 525, XP002164973
S. KOTO ET AL.: "Some 2,3,4,6-tetra-O-(p-chlorobenzyl)-alfa-D-hexopyranoses", CARBOHYDRATE RESEARCH, vol. 87, 1980, pages 294 - 296, XP002164974
A. PÜSCHL, J. KEHLER, O. DAHL: "Solution phase synthesis of dithymidine phosphorothioate by a phosphotriester method using new S-protecting groups", NUCLEOSIDES & NUCLEOTIDES, vol. 16, 1997, pages 145 - 158, XP002164975
J.T. KOVALAINEN ET AL.: "Synthesis and in vitro pharmacology of a series of new chiral histamine H3-receptor ligands: 2-(R and S)-amino-3-(1H-imidazol-4(5)-yl)propyl ether derivatives", J. MED. CHEM., vol. 42, 1999, pages 1193 - 1202, XP002164976
"Catalog Handbook of Fine Chemicals 1996-1997", ALDRICH, NEDERLAND, 1996, XP002164979
S. BUDAVARI (ED): "The Merck index", 1996, MERCK & CO, WHITEHOUSE STATION, NJ, XP002164980
S. BUDAVARI (ED): "The Merck index", 1996, MERCK & CO, WHITEHOUSE STATION, NJ, XP002164981
J.F. HARTWIG: "Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates: scope and mechanism", ANGEW. CHEM. INT. ED., vol. 37, 1998, pages 2047 - 2067, XP002164977
O.J. PLANTE, S.L. BUCHWALD, P.H. SEEBERGER: "Halobenzyl ethers as protecting groups for organic synthesis", J. AM. CHEM. SOC., vol. 122, 2000, pages 7148 - 7149, XP002164978
See also references of EP 1233970A2
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