1H NMR chemical shift studies of pregn-5-ene-3β,20(R)-diol and pregn-5-ene-3β-ol,20-one d-glucopyranoside derivatives

✍ Scribed by J.D Warthen Jr.; R.M Waters; J.E Oliver

• Publisher: Elsevier Science
• Year: 1990
• Tongue: English
• Weight: 480 KB
• Volume: 46
• Category: Article
• ISSN: 1386-1425
• DOI: 10.1016/0584-8539(90)80107-a

✦ Synopsis

The 'HNMR chemical shift and J value data of a series of pregn-S-ene-38,20(R)-diol/pregn-5-ene-38-ol,20-one D-glucopyranosides and D-glucopyranoside derivatives are reported because of their relevance to the structure determination of pregnenediol tri-and diglucosides on tobacco hornworm eggs. Effects of various substituents at the 3/3-and 20(R)-positions of the pregn-5-ene nucleus upon chemical shifts of selected protons on the pregn-5-ene nucleus are discussed. Chemical shifts of selected protons on the Dglucopyranoside nucleus/nuclei are also discussed. Differentiation between the pregn-S-ene substitution points, between anomeric glucose configurations and between anomeric protons on p-D-glucosides at 38 and 20(R) is demonstrated. A COSY NMR analysis of the Manduca peracetylated triglucoside is utilized to show the interaction of the three anomeric p-D-glucoside protons and to distinguish the dissimilar one.