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A highly stereoselective β-(1→4)-glycosidic bond formation by reductive cleavage of cyclic orthoesters

✍ Scribed by Takamasa Iimori; Hiro Ohtake; Shiro Ikegami

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
230 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

Sterically congested glycosides, glycosyl-13-(1--->4)-glycosides, were stereoselectively synthesized by reduction of glycosidic spiro-orthoesters with LiAIH4-AICI3. This novel transformation is especially valuable when it is applied to the preparation of mannosyl-13-(1--->4)-glycoside which must be one of the most difficult tasks in carbohydrate chemistry.

📜 SIMILAR VOLUMES

ChemInform Abstract: A Highly Stereosele
ChemInform Abstract: A Highly Stereoselective β-(1→4)-Glycosidic Bond Formation by Reductive Cleavage of Cyclic Orthoesters.
✍ T. IIMORI; H. OHTAKE; S. IKEGAMI 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 35 KB 👁 1 views

A Highly Stereoselective β-(1→4)-Glycosidic Bond Formation by Reductive Cleavage of Cyclic Orthoesters. -Reduction of the orthoester (I) under the conditions shown provides the desired glycoside (II) with high β-selectivity. Application of a LiAlH4/AlCl3 reagent to the glycosidic spiro-orthoesters

ChemInform Abstract: A Highly Stereosele
ChemInform Abstract: A Highly Stereoselective Construction of β-Glycosyl Linkages by Reductive Cleavage of Cyclic Sugar Orthoesters.
✍ Hiro Ohtake; Naoto Ichiba; Shiro Ikegami 📂 Article 📅 2001 🏛 John Wiley and Sons ⚖ 43 KB 👁 1 views

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