3-Oxo-3-phosphapentopyranoses. -Addition of methyl phosphinate (III) to dialdehyde (II), which is readily accessible by periodate cleavage of methyl β-D-arabinoside (I), affords 3-phosphapentopyranose (IV) as mixture of all eight possible diastereomers (no yield given). -(FOOKES, C.
3-oxo-3-phosphapentopyranoses
✍ Scribed by Christopher J. R. Fookes; Michael J. Gallagher
- Publisher
- John Wiley and Sons
- Year
- 1996
- Tongue
- English
- Weight
- 444 KB
- Volume
- 7
- Category
- Article
- ISSN
- 1042-7163
No coin nor oath required. For personal study only.
✦ Synopsis
Addition of methyl phosphinate to 2(R)-methoxy 3-oxapentanedial gives all eight possible diastereoisomeric 3-phosphapentopyranoses in very poor yield. Structures and stereochemistry are assigned on the basis of 'H, 318 NMR, and mass spectroscopy of their acetates.
📜 SIMILAR VOLUMES
The context of this project and other approaches are discussed in more detail in [I] and also in the preceding paper 131. 'H-NMR (80 MHz, CDCI,): 1.4 1.8 (m, 2 main peaks, 3 H-C(2')); 4.75 (m. wx % 7,2 H-C(2), 2 H-C(4)); 5.2-5.6 (m. H-C(1')); 7.25-7.75 (m. C6H5CO). MS: 187 (16, Mc'), 172 (2), 105 (l
## Abstract magnified image A facile approach was developed on assembly of the 2‐pyridone nucleus by ferric chloride promoted [3+3] cycloaddition in propionic acid. The tandem process involves cyclization of Michael adduct followed by aromatization. Thus, different substituted 1,2‐dihydro‐2‐oxo‐3‐
## Abstract A one‐step ‘ring switching’ transformation of (__S__)‐3‐[(dimethylamino)methylidene]‐5‐(methoxycarbonyl)tetrahydrofuran‐2‐one (**4**) with 2‐pyridineacetic acid derivatives (**5–7**) and 2‐aminopyridines (**8, 9**) afforded the corresponding 3‐(4‐oxo‐4__H__‐quinolizinyl‐3)‐ **(15–17)**