195875-23-1

Upstream product

• 63593-02-2 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 195519-72-3 (E)-3-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-prop-2-en-1-ol 

Relevant academic research and scientific papers

114. Aza-claisen rearrangement: Synthesis of 5'-branched 5'- aminothymidines

The syntheses of both diastereoisomers of 5'-ethyl-substituted thymidine dimers, the (5'R)- and (5'S)-configurated 33a and 33b, respectively, in which the natural phosphodiester linkage is replaced by an amide group (C(3')- CH2CONH-CH(5')(Et)), are described. Their fully protected derivatives 35a and 35b, respectively, are suitable for incorporation into antisense oligonucleotides. Unexpectedly, an attempted Pd(II)-catalysed aza-Claisen rearrangement of trichloroacetimidate 7 provided the diastereoisomerically pure cyclopropane derivative 17, whose structure was confirmed by X-ray analysis.