117770-16-8Relevant articles and documents
A divergent, short, and stereoselective approach to pyrrolidine iminosugars: Synthesis of 1,4-dideoxy-1,4-imino-derivatives of d-allitol, d-ribitol, ethyl-erythritol, and (-)-2,3-trans-3-4-cis-dihydroxyproline
Chirke, Sahadev S.,Rajender, Anugula,Lakshmi, Jerripothula K.,Rao, Batchu Venkateswara
, p. 1218 - 1221 (2015)
A highly stereoselective addition of Grignard reagent on lactamine for the synthesis of 1,4-dideoxy-1,4-imino-derivatives of d-allitol, d-ribitol, ethyl-erythritol, and (-)-2,3-trans-3-4-cis-dihydroxyproline has been described from commercially available d-ribose as a starting material.
Enantioselective synthesis of hydroxylated pyrrolidines via Sharpless epoxidation and olefin metathesis
Murruzzu, Caterina,Riera, Antoni
, p. 149 - 154 (2007/10/03)
The enantioselective synthesis of polyhydroxylated pyrrolidines from enantiomerically pure 2,3-epoxy-pent-4-en-1-ol 5 is described herein. The epoxy alcohol, readily available in any configuration by Sharpless epoxidation, was submitted to regioselective C-3 ring-opening with allyl amine, Boc-protection and ring-closing metathesis to yield dehydropyrrole derivative 7. From this key intermediate, 1,4-dideoxy-1,4-imino-d-ribitol (+)-3 and 1,4-dideoxy-1,4-imino-d-allitol (+)-4 were prepared in high yields. The enantiomers of these compounds can be obtained by the same sequence starting from an epoxy alcohol with the opposite configuration.
Stereoselective synthesis of 1,4-dideoxy-1,4-imino-D-allitol and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline
Madhan,Venkateswara Rao
, p. 5641 - 5643 (2007/10/03)
A stereoselective synthesis of 1,4-dideoxy-1,4-imino-D-allitol 1 and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline was achieved via the addition of vinylmagnesium bromide to the benzylimine derived from (R)-2,3-O-isopropylidene glyceraldehyde followed by N-allylation, ring-closing metathesis (RCM), and dihydroxylation.
