Date published: 2026-4-26

1-800-457-3801

SCBT Portrait Logo
Seach Input

2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl Trichloroacetimidate (CAS 121238-27-5)

0.0(0)
Write a reviewAsk a question

CAS Number:
121238-27-5
Molecular Weight:
492.69
Molecular Formula:
C16H20Cl3NO10
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

QUICK LINKS

2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl Trichloroacetimidate is a chemical compound extensively used in carbohydrate chemistry research due to its role as a glycosyl donor in glycosylation reactions. In these reactions, the trichloroacetimidate moiety serves as an excellent leaving group, facilitating the transfer of the α-D-mannopyranosyl residue onto acceptor molecules. This compound has been employed in the synthesis of various glycoconjugates, including oligosaccharides, glycopeptides, and glycolipids, which are crucial for studying carbohydrate-protein interactions, cell recognition processes, and pathogen-host interactions. Researchers utilize 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl Trichloroacetimidate to investigate the structure-function relationships of carbohydrates and their involvement in biological processes. Additionally, it is utilized in the synthesis of carbohydrate-based materials with applications in drug delivery systems, biomaterials, and diagnostics. Its ability to efficiently introduce α-linked mannopyranosyl residues into various molecules makes it a valuable tool for synthesizing complex glycoconjugates and probing their roles in biological systems. Through its use in research, this compound contributes to advancing our understanding of carbohydrate biology and developing novel carbohydrate-based materials for diverse applications in biotechnology and materials science.


2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl Trichloroacetimidate (CAS 121238-27-5) References

  1. A facile and effective synthesis of alpha-(1-->6)-linked mannose di-, tri-, tetra-, hexa-, octa-, and dodecasaccharides, and beta-(1-->6)-linked glucose di-, tri-, tetra-, hexa-, and octasaccharides using sugar trichloroacetimidates as the donors and unprotected or partially protected glycosides as the acceptors.  |  Zhu, Y. and Kong, F. 2001. Carbohydr Res. 332: 1-21. PMID: 11403082
  2. From solution phase to 'on-column' chemistry: trichloroacetimidate-based glycosylation promoted by perchloric acid-silica.  |  Mukhopadhyay, B., et al. 2005. J Org Chem. 70: 9059-62. PMID: 16238354
  3. Mannose-pepstatin conjugates as targeted inhibitors of antigen processing.  |  Free, P., et al. 2006. Org Biomol Chem. 4: 1817-30. PMID: 16633575
  4. A comparative study of different glycosylation methods for the synthesis of D-mannopyranosides of Nalpha-fluorenylmethoxycarbonyl-trans-4-hydroxy-L-proline allyl ester.  |  Lee, DJ., et al. 2007. Carbohydr Res. 342: 2628-34. PMID: 17854783
  5. On the origin of the regioselectivity in glycosylation reactions of 1,2-diols.  |  Cid, MB., et al. 2009. Org Biomol Chem. 7: 1471-81. PMID: 19300834
  6. Monovalent mannose-based DC-SIGN antagonists: targeting the hydrophobic groove of the receptor.  |  Tomašić, T., et al. 2014. Eur J Med Chem. 75: 308-26. PMID: 24556146
  7. Synthesis of high-mannose oligosaccharide analogues through click chemistry: true functional mimics of their natural counterparts against lectins?  |  François-Heude, M., et al. 2015. Chemistry. 21: 1978-91. PMID: 25483029
  8. Synthesis of a fucosylated and a non-fucosylated core structure of xylose-containing carbohydrate chains from N-glycoproteins.  |  van der Ven, JG., et al. 1994. Carbohydr Res. 264: 45-62. PMID: 8001019
  9. Synthesis of three tetrasaccharides containing 3-O-methyl-D-mannose, as model compounds for xylose-containing carbohydrate chains from N-glycoproteins.  |  van der Ven, JG., et al. 1994. Carbohydr Res. 253: 121-39. PMID: 8156544
  10. Synthesis of a 3, 4‐Di‐O‐substituted Heptose Structure: A Partial Oligosaccharide Expressed in Neisserial Lipooligosaccharide  |  Kubo, H., Ishii, K., Koshino, H., Toubetto, K., Naruchi, K., & Yamasaki, R. 2004. European Journal of Organic Chemistry. 2004(6): 1202-1213.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl Trichloroacetimidate, 500 mg

sc-213981
500 mg
$360.00