1310019-06-7

Upstream product

• 85951-12-8 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside 
• 103931-45-9 5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose 
• 1310019-05-6 1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-deoxy-3-benzylamino-α-D-ribofuranose 

Downstream Products

• 1310019-02-3 (2S,3R,4S,5S)-2-allyl-5-(acetoxymethyl)-4-benzylamino-tetrahydrofuran-3-ol 

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.