71020-96-7

Upstream product

• 34626-95-4 1,2:3,4-di-O-isopropylidene-β-D-psicofuranose 
• 100-39-0 benzyl bromide 
• 18422-54-3 1,2;4,5-di-O-isopropylidene-β-D-fructopyranose 
• 100-44-7 benzyl chloride 
• 67-64-1 acetone 
• 69351-19-5 Shi's ketone 
• 6347-01-9 fructopyranose 

Downstream Products

• 133886-01-8 2-azido-2-deoxy-6-O-benzyl-3,4-O-isopropylidene-β-D-psico-furanose 
• 86049-38-9 5-((benzyloxy)methyl)-furan-2-carbaldehyde 
• 145121-55-7 6-O-benzyl-3,4-O-isopropylidene-β-D-psicofuranosyl cyanide 
• 145121-54-6 6-O-benzyl-3,4-O-isopropylidene-α-D-psicofuranosyl cyanide 
• 145121-59-1 2-allyl-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-β-D-psicofuranose 
• 364635-26-7 ((3aR,4R,6R,6aR)-4-Azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-trimethyl-silane 
• 874812-28-9 1-[6-O-benzyl-3,4-O-isopropylidene-β-D-psicofuranosyl]thymine 
• 71021-04-0 (2R,3R,4S,5R)-5-Benzyloxymethyl-2-hydroxymethyl-tetrahydro-furan-2,3,4-triol 

Relevant academic research and scientific papers

Synthesis and antiviral activity of novel spirocyclic nucleosides

The synthesis of a number of spirocyclic ribonucleosides containing either a triazolic or azetidinic system is described, along with two analogous phosphonate derivatives of the former. These systems were constructed from the same β-d-psicofuranose starti

Synthesis of 2-amino-2,4-anhydro-3-O-(2-tetrahydropyranyl)-psicofuranose: A versatile intermediate for S-type locked nucleosides

2-Amino-2,4-anhydro-psicofuranose derivative was synthesized starting from d-fructose.

Novel synthesis of (+)-hydantocidin based on the plausible biosynthetic pathway

The title synthesis was examined by employing two synthetic schemes which feature N,O-spiroketal formation as a key step. Although the stepwise synthesis starting with D-fructose and proceeding through the D-psicose derivatives successfully produced a mixture of (+)-hydantocidin (1) and its C5-epimer [(-)-5-epihydantocidin (2)], the one-step synthesis utilizing D-isoascorbic acid and urea as starting materials was found to give 2 more selectively than 1. Studies on the key N,O-spiroketal formation and epimerization between 1 and 2 were also carried out to explore some novel aspects of the obtained results.

A novel biogenetic type synthesis of (+)-hydantocidin

The title synthesis was accomplished by featuring the proposed biosynthetic pathway. The synthesis commenced with the D-psicose derivative readily obtainable from D-fructose and employed intramolecular N, O-spiroketal formation of the open-chain N-acylurea derivative as a key step.

Synthetic studies on (+)-hydantocidin (3): A new synthetic method for construction of the spiro-hydantoin ring at the anomeric position of D-ribofuranose

A facile synthetic route for the large-scale preparation of a herbicidal natural product, (+)-hydantocidin is described. The protected D-psicose 6, prepared in five steps from D-fructose, was stereospecifically converted to azido-amide 14 by N-glycosidation (TMSN3/TMSOTf), oxidation and animation. Hydantoin ring-construction on 14 was achieved by aza-Wittig reaction (PBu3/CO2/CH3CN) to give 16 without epimerization at the anomeric center. After acetylation, stepwise deprotection of 24 afforded (+)-hydantocidin 1 in 16% overall yield from D-fructose.

Synthesis of 5- and 6-O-Alkyl substituted Ketohexoses of the L-sorbo-, L-psico-, D-fructo-, and D-tagato-Series

Starting from methyl 1,3-O-benzyliden-β-D-fructopyranoside 1 the synthesis of 5-O-benzyl-D-fructose 9 and, after inversion of the configuration at C-4 by oxydation and subsequent stereoselective reduction, the synthesis of 5-O-benzyl- and 5-O-methyl-D-tag