Oleandrose

Oleandrose

Names
IUPAC name 2,6-Dideoxy-3-O-methyl-L-arabino-hexose
Systematic IUPAC name (3S,4S,5S)-4,5-Dihydroxy-3-methoxyhexanal
Other names 2,6-Dideoxy-3-O-methyl-L-arabinohexose
Identifiers
CAS Number	13089-77-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:10423
ChemSpider	4574484
KEGG	C08237
PubChem CID	5461155
UNII	C9TRD5E7IQ
InChI InChI=1S/C7H14O4/c1-5(9)7(10)6(11-2)3-4-8/h4-7,9-10H,3H2,1-2H3/t5-,6-,7-/m0/s1 Key: GOYBREOSJSERKM-ACZMJKKPSA-N
SMILES C[C@@H]([C@@H]([C@H](CC=O)OC)O)O
Properties
Chemical formula	C7H14O4
Molar mass	162.185 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Oleandrose is a type of carbohydrate with the chemical formula C₇H₁₄O₄. With a six-carbon chain, it is classified as a hexose. With two hydroxyl groups replaced with hydrogen atoms, it is a dideoxy sugar. The hydroxyl group at C3 is methylated.

Occurrence

Oleandrdose is found in the leaves of Nerium oleander and may contribute to the toxicity of the plant. ^{[1] [2]} Oleandrose is also a component of several naturally occurring chemical compounds including the avermectins (emamectin, abamectins, ivermectin, and others), the macrolide antibiotic oleandomycin, and the cardiac glycoside oleandrin.

Laboratory syntheses of L-oleandrose ^[3] and DL-oleandrose ^[4] have been reported.

See also

• Sarmentose, a diastereomeric dideoxy sugar

References

1. Siddiqui, Bina Shaheen; Khatoon, Nasima; Begum, Sabira; Farooq, Ahsana Dar; Qamar, Kehkashan; Bhatti, Huma Aslam; Ali, Syed Kashif (2012). "Flavonoid and cardenolide glycosides and a pentacyclic triterpene from the leaves of Nerium oleander and evaluation of cytotoxicity". Phytochemistry. 77: 238–244. Bibcode:2012PChem..77..238S. doi:10.1016/j.phytochem.2012.01.001. PMID   22281382.
2. Bakir Çilesizoğlu, Neşe; Yalçin, Emine; Çavuşoğlu, Kültiğin; Sipahi Kuloğlu, Selin (2022). "Qualitative and quantitative phytochemical screening of Nerium oleander L. Extracts associated with toxicity profile". Scientific Reports. 12 (1): 21421. Bibcode:2022NatSR..1221421B. doi:10.1038/s41598-022-26087-0. PMC   9742154 . PMID   36504046.
3. Bredenkamp, Martin W.; Holzapfel, Cedric W.; Toerien, Francois (1992). "Alternative Syntheses of L-(-)-Oleandrose from L-Rhamnose¹Preparation of Glycals". Synthetic Communications. 22 (17): 2459–2477. doi:10.1080/00397919208021642.
4. Berti, G.; Catelani, G.; Colonna, F.; Monti, L. (1982). "A highly diastereoselective synthesis of dl-oleandrose". Tetrahedron. 38 (20): 3067–3072. doi:10.1016/0040-4020(82)80194-4.