Tri-O-benzyl-D-galactal (CAS 80040-79-5)
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Tri-O-benzyl-D-galactal is a compound that has applications in organic synthesis and carbohydrate chemistry research. It is used as an intermediate in the preparation of complex glycoconjugates due to its protected form, which allows for selective deprotection and further chemical modification. The compound is particularly useful in the study of stereoselective glycosylation reactions, where it is employed to understand the formation of glycosidic bonds and the factors influencing anomeric selectivity. Researchers also utilize Tri-O-benzyl-D-galactal in the synthesis of glycosidase inhibitors, exploring its role in mimicking the transition state of carbohydrate hydrolysis. Additionally, this compound is used in the preparation of chiral auxiliaries and catalysts that are relevant in asymmetric synthesis, which is for the production of enantiomerically pure substances.
Tri-O-benzyl-D-galactal (CAS 80040-79-5) References
- Stereoselective synthesis of C-[2-S-(p-tolyl)-2-thio-beta-D-galactopyranosyl] compounds using the reaction of TolSCl adducts of D-galactal with C-nucleophiles. | Han, M., et al. 2000. Carbohydr Res. 323: 202-7. PMID: 10782302
- Rhenium(V)-catalyzed synthesis of 2-deoxy-alpha-glycosides. | Sherry, BD., et al. 2004. J Am Chem Soc. 126: 4510-1. PMID: 15070356
- An efficient synthesis of 2,3-dideoxy-alpha,beta-unsaturated carbohydrate enals by mixed Lewis acid (HfCl4 and ZnI2) catalyzed hydration of glycals. | Saquib, M., et al. 2006. Carbohydr Res. 341: 1052-6. PMID: 16564512
- Remarkable oxidation stability of glycals: excellent substrates for cerium(IV)-mediated radical reactions. | Linker, T., et al. 2008. J Am Chem Soc. 130: 16003-10. PMID: 18975872
- Synthesis of fused pyran-carbahexopyranoses as glycosidase inhibitors. | Doddi, VR., et al. 2009. Carbohydr Res. 344: 606-12. PMID: 19217083
- Glycosyl hydroperoxides derived from 2-deoxysugars. | Szechner, B., et al. 2010. Carbohydr Res. 345: 2464-8. PMID: 20933224
- The synthesis of 2-deoxy-α-D-glycosides from D-glycals catalyzed by TMSI and PPh3. | Cui, XK., et al. 2012. Carbohydr Res. 358: 19-22. PMID: 22854184
- Synthesis of 2-fluoro and 4-fluoro galactopyranosyl phosphonate analogues of UDP-Gal. | Jambal, I., et al. 2012. Carbohydr Res. 360: 31-9. PMID: 22975276
- A double diastereoselective Michael-type addition as an entry to conformationally restricted tn antigen mimics. | Aydillo, C., et al. 2013. J Org Chem. 78: 10968-77. PMID: 24083620
- N-halosuccinimide/AgNO3-efficient reagent systems for one-step synthesis of 2-haloglycals from glycals: application in the synthesis of 2C-branched sugars via Heck coupling reactions. | Dharuman, S. and Vankar, YD. 2014. Org Lett. 16: 1172-5. PMID: 24499471
- Iridium-promoted deoxyglycoside synthesis: stereoselectivity and mechanistic insight. | Pal, KB., et al. 2020. Chem Sci. 12: 2209-2216. PMID: 34163986
- Inverse-electron demand Diels Alder Reactions between glycals and tetrazines. | Marzabadi, CH., et al. 2022. Carbohydr Res. 519: 108623. PMID: 35738050
- Oxidation of Glycals with Hydrogen Peroxide | and Danuta Mostowicz, Margarita Jurczak, Hans-Jurgen Hamann, Eugen Höft, Marek Chmielewski. November 1998. European Journal of Organic Chemistry. Volume1998, Issue11: Pages 2617-2621.
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Tri-O-benzyl-D-galactal, 1 g | sc-258279 | 1 g | $224.00 |