82921-68-4

Upstream product

• 174392-13-3 3-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)prop-1-ene 
• 62410-12-2 1,5-di-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranose 
• 82921-64-0 1-O-acetyl-5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranose 
• 762-72-1 allyl-trimethyl-silane 

Downstream Products

• 1352789-16-2 3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)propan-1-ol 
• 1352789-20-8 3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranosyl-1-yl)propanal 
• 1352789-23-1 3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)prop-1-yl methanesulfonate 
• 1352789-28-6 3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)propyl-1-azide 
• 1352789-32-2 3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-β-D-ribofuranos-1-yl)propyl-1-amine 
• 1352789-39-9 (3R,S)-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)pent-4-yn-3-ol 
• 1352789-41-3 (3R,S)-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)-5-phenylpent-4-yn-3-ol 
• 1352789-43-5 1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)pent-4-yn-3-one 
• 1352789-45-7 1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)-5-phenylpent-4-yn-3-one 

Relevant academic research and scientific papers

A versatile approach to alcohol, aldehyde, ketone and amine derivatives starting from β-allyl C-glycosides of D-ribofuranose and 2-deoxy-D-ribofuranose

An efficient preparative procedure is described, leading from β-allyl C-glycosides of d-ribofuranose to alcohols by a hydroboration-oxidation procedure. The corresponding aldehydes were obtained by Swern or Dess-Martin oxidation. Alternatively, two of the alcohols were mesylated to gain access to azides and amines. Treatment of the aldehydes with ethynylmagnesium bromide or phenylethynyllithium and consecutive oxidation of the diastereomeric alcohols provided the acetylenic ketones in good to excellent yields. The obtained derivatives serve as important intermediates for the synthesis of various heterocyclic systems. Georg Thieme Verlag Stuttgart New York.

Peracetylated β-allyl C-glycosides of D-ribofuranose and 2-deoxy-D-ribofuranose in the chemical literature: Until now, mirages in the literature

The peracetylated β-allyl C-glycosides of D-ribofuranose (8) and 2-deoxy-D-ribofuranose (13) were stereoselectively prepared via the isopropylidene derivatives 3 and 4. These reactions represent what are, to the best of our knowledge, the first preparation of these apparently simple derivatives whose structures were carefully proved by NMR and X-ray investigations. Publications which allegedly described the synthesis of 8 and 13 were critically examined. Georg Thieme Verlag Stuttgart.