The efficient synthesis of a bis-glycosylated steroid drug transport reagent: Methyl 3-β-amino-7α, 12α-di(1′α-glucosyl)-5β-cholate (TC002)
| Autor: | Natan A. Kogan, Y. W. Hui, Richard G. Dulina, Michael J. Sofia, Dashan Liu, Thomas Wagler, Ramesh Kakarla, Anna Chen, Nicole T. Hatzenbuhler |
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| Rok vydání: | 1997 |
| Předmět: |
chemistry.chemical_classification
Chemistry medicine.medical_treatment Organic Chemistry Clinical Biochemistry Pharmaceutical Science Glycoside Sulfoxide Biochemistry Medicinal chemistry Chemical synthesis Steroid carbohydrates (lipids) chemistry.chemical_compound Aldose Reagent Yield (chemistry) Drug Discovery medicine Molecular Medicine Drug carrier Molecular Biology |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 7:2251-2254 |
| ISSN: | 0960-894X |
| DOI: | 10.1016/s0960-894x(97)00410-1 |
| Popis: | The drug transport reagent, methyl 3-β-amino-7α, 12α-di(1′α-glucosyl)-5β-cholate (TC002) 1 was prepared in 15% overall yield from pentaacetyl glucose and methyl cholate. Pentaacetyl glucose was converted to glucosyl sulfoxide 2 in 56% overall yield. Methyl cholate was converted to methyl 3-β-azido cholate 3 in 67% yield. Bis-glycosylation of 3 with 2 followed by a single step reduction provided 1. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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