Regioselective ketalization (dioxane vs dioxolane) study of internal diastereomeric 1,2,3-triol systems obtained from D-pentoses

被引：2

作者：

Donthulachitti, Chiranjeevi ^{[2
]}

Ramakrishna, Yelukala ^{[2
]}

Shekunti, Ravikumar ^{[2
]}

Neella, Chandra Kiran ^{[1
]}

机构：

[1] Palamuru Univ, Dept Chem, Mahabubnagar 509001, Telangana State, India

[2] Palamuru Univ, Dept MSc 5Yr Integrated Chem, Mahabubnagar 509001, Telangana State, India

来源：

RESULTS IN CHEMISTRY | 2022年 / 4卷

关键词：

Regioselective acetonide protection; Syn/anti acetonides; Dioxanes; Dioxolanes;

D O I：

10.1016/j.rechem.2022.100341

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ringselective and regioselective acetonide protection of four diastereomeric triol systems (ribo & xylo with 1,3syn configuration and arabino & lyxo with 1,3-anti configuration) were studied and certain useful generalizations are drawn as follows. Three triol systems i.e. xylo, arabino and lyxo triol systems have preferred only five membered acetonides (dioxolanes) over six membered acetonides (dioxanes). Selective formation of five membered anti acetonides was noticed when there is a competition between syn and anti acetonide formation. If the acetonides formed from any triol system are either syn or anti, then only allylic acetonides are favoured over non-allylic acetonnides. Only ribo-triol system formed six membered syn acetonides (thermodynamic control). No triol has produced all the three acetonides. All the ring sizes were unambiguously confirmed by employing Evan's 13C NMR method supported by 1H NMR spectroscopy. These chiral building blocks with predefined stereochemistry and multiple functional groups can be potential scaffolds for total synthesis.

引用

页数：5