1310019-01-2

Upstream product

• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 100-52-7 benzaldehyde 
• 31504-85-5 3,5-O-benzylidene-1,2-O-isopropylidene-α-D-xylofuranose 
• 34311-63-2 5-O-benzyl-3-oxo-1,2-O-isopropylidene-α-D-xylofuranose 
• 1310018-99-5 1,2-O-isopropylidene-5-O-benzyl-3-deoxy-3-benzylamino-α-D-ribofuranose 
• 1310019-04-5 1,2-O-isopropylidene-5-O-benzyl-3-deoxy-3-dibenzylamino-α-D-ribofuranose 
• 762-72-1 allyl-trimethyl-silane 
• 23202-83-7 5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 

Relevant academic research and scientific papers

High 1,3-trans stereoselectivity in nucleophilic substitution at the anomeric position and β-fragmentation of the primary alkoxyl radical in 3-amino-3-deoxy-ribofuranose derivatives: Application to the synthesis of 2- epi -(-)-jaspine B

The high inverse stereoselectivity in the nucleophilic substitution at the anomeric position of 3-amino-3-deoxy-ribofuranose derivatives is reported. This unprecedented stereoselectivity is explained in terms of preferential nucleophilic attack on the "inside face" of the respective five-membered ring oxocarbenium ion that orients pseudoequatorially to the benzylamine group placed at the C-3 position. In addition, an unusual β-fragmentation of a primary alkoxyl radical generated from its corresponding N-phthalimide derivative was achieved, and thus taking advantages of both reactions, the total synthesis of 2-epi-(-)-jaspine B was completed.