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Review
. 2012:67:95-136.
doi: 10.1016/B978-0-12-396527-1.00003-6.

Strategies in synthesis of heparin/heparan sulfate oligosaccharides: 2000-present

Steven B Dulaney  1 , Xuefei Huang
Affiliations
Review

Strategies in synthesis of heparin/heparan sulfate oligosaccharides: 2000-present

Steven B Dulaney et al. Adv Carbohydr Chem Biochem. 2012.
No abstract available

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Figures

Scheme 1
Scheme 1
(A) Structures of heparin/HS; (B) structure of fondaparinux (Arixtra®). (Note idose and iduronic acid are arbitrarily presented in the 1C4 conformation following common usage in the field. This does not necessarily represent the conformations in solution of the various heparin derivatives depicted throughout the article.)
Scheme 2
Scheme 2
Various routes for inverting D-glucose to L-idose derivatives.
Scheme 3
Scheme 3
Recent routes to monosaccharide precursors of L-IdoA.
Scheme 4
Scheme 4
Conversion of glycopyranosides into uronic acids in synthesis of heparin/HS oligosaccharides.
Scheme 5
Scheme 5
Comparison of glycosyl bromide and trichloroacetimidate donors in glycosylation.
Scheme 6
Scheme 6
Strategies for enhancing stereoselectivity in glycosylation.
Scheme 7
Scheme 7
Synthesis of all potential heparin/HS disaccharides from eight monosaccharide precursors.
Scheme 8
Scheme 8
Disaccharide derivative 43 can be orthogonally deprotected for sulfation at various locations.
Scheme 9
Scheme 9
Evaluation of TCE sulfate ester-containing donors and acceptors in glycosylation reactions.
Scheme 10
Scheme 10
Linear synthesis of oligosaccharides from the reducing end.
Scheme 11
Scheme 11
A linear synthesis of the heparin/HS trisaccharides responsible for binding with the fibroblast growth factors FGF-1 and FGF-2.
Scheme 12
Scheme 12
Linear synthesis and late-stage oxidation to generate trisaccharide 78.
Scheme 13
Scheme 13
Solid-supported synthesis of heparin oligomers.
Scheme 14
Scheme 14
Use of the water-soluble polymer MPEG in synthesis of heparin/HS oligosaccharides.
Scheme 15
Scheme 15
Soluble polymers anchored through the carboxylate group of the iduronic component.
Scheme 16
Scheme 16
Protected amino linker used in conjunction with monosaccharide building blocks used in solid-supported synthesis of heparin/HS oligosaccharides.
Scheme 17
Scheme 17
The active–latent glycosylation strategy.
Scheme 18
Scheme 18
Active–latent synthesis of dodecamer 109.
Scheme 19
Scheme 19
Active–latent synthesis with silyl protecting groups.
Scheme 20
Scheme 20
Synthesis of one of the eight disaccharide building blocks used by Boons and coworkers to prepare a library of heparin oligosaccharides.
Scheme 21
Scheme 21
The use of the 1,6-anhydro sugars in latent–active strategy.
Scheme 22
Scheme 22
Glycosylation strategy employing selective activation.
Scheme 23
Scheme 23
Synthesis utilizing the selective activation of trichloroacetimidate donors in the presence of thioglycoside acceptors.
Scheme 24
Scheme 24
Congruent use of hemiacetals and thioglycosides.
Scheme 25
Scheme 25
The armed–disarmed strategy for chemoselective glycosylation relies on differences in anomeric reactivities of the building blocks.
Scheme 26
Scheme 26
(A) Monosaccharide building blocks used in Wong’s synthesis of heparin components; (B) preparation of disaccharide building block 154; (C) one-pot synthesis of heparin pentasaccharide precursor 156 by the armed–disarmed strategy.
Scheme 27
Scheme 27
Pre-activation-based strategy for glycosylation.
Scheme 28
Scheme 28
Divergent synthesis of the building blocks needed for the assembly of a hexasaccharide library.
Scheme 29
Scheme 29
Enzymatic synthesis of pentasaccharide 178 from “heparosan.”
Scheme 30
Scheme 30
The chemoenzymatic synthesis of heparin heptasaccharides 183 and 184.
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