Estrone tetraacetylglucoside

Estrone tetraacetylglucoside

Identifiers
IUPAC name [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-{[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy}oxan-2-yl]methyl acetate
CAS Number	27610-08-8
PubChem CID	102146562
ChemSpider	26594301
CompTox Dashboard (EPA)	DTXSID901046420
Chemical and physical data
Formula	C32H40O11
Molar mass	600.661 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(=O)OCC1OC(Oc2ccc3C4CCC5(C)C(CCC5=O)C4CCc3c2)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O
InChI InChI=1S/C32H40O11/c1-16(33)38-15-26-28(39-17(2)34)29(40-18(3)35)30(41-19(4)36)31(43-26)42-21-7-9-22-20(14-21)6-8-24-23(22)12-13-32(5)25(24)10-11-27(32)37/h7,9,14,23-26,28-31H,6,8,10-13,15H2,1-5H3 Key:IMZSXCARTLIDBP-UHFFFAOYSA-N

Estrone tetraacetylglucoside (brand name Glucovex, Glycovex) is a semisynthetic, steroidal estrogen. ^[1] It is an estrogen ester, specifically, an ester of estrone. ^[1] The drug was marketed since at least 1942. ^[2]

Synthesis: ^{[3] [4]}

References

1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 900. ISBN   978-1-4757-2085-3.
2. Jacobson O (1947). Heredity in breast cancer, a genetic and clinical study of two hundred probands. Munksgaard. p. 251.{{cite book}}: |work= ignored (help)
3. Bernstein, S., Conrow, R. B. (April 1971). "Steroid conjugates. VI. Improved Koenigs--Knorr synthesis of aryl glucuronides using cadmium carbonate, a new and effective catalyst". The Journal of Organic Chemistry. 36 (7): 863–870. doi:10.1021/jo00806a001.
4. Paquet, A., Layne, D. S. (1 December 1973). "Reactivity of the Thallium(I) Salts of 3-Hydroxy-1,3,5(10)-estratrien-17-one and 1,3,5(10)-Estratriene-3,17β-diol. Preparation of 17-Oxoestra-1,3,5(10)-trien-3-yl 2′-Acetamido-3′,4′,6′-tri- O -acebtyl-2′-deoxy-β- D -glucopyranoside". Canadian Journal of Chemistry. 51 (23): 3855–3859. doi:10.1139/v73-575.