178931-91-4

Upstream product

• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 73111-16-7 3,4,5-tri-O-benzyl-1,2-dideoxy-L-xylo-hex-1-enitol 
• 921770-88-9 (1R,4S)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopent-2-en-1-ol 
• 727428-98-0 (S)-(S)-5-(1,4-Dioxa-spiro[4.5]dec-2-yl)-hepta-1,6-dien-3-ol 
• 921770-98-1 [(1R,2R,3R,4R)-2,3-bis(benzyloxy)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopent-1-yloxy]-tert-butyl-dimethylsilane 
• 921771-07-5 (2S)-2-[(1R,2R,3R,4S)-2,3,4-tris(benzyloxy)cyclopent-1-yl]-1,4-dioxaspiro[4.5]decane 
• 921770-99-2 (1R,2S,3R,4R)-2,3-bis(benzyloxy)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopentanol 
• 921771-08-6 (S)-1-((1R,2R,3R,4S)-2,3,4-Tris-benzyloxy-cyclopentyl)-ethane-1,2-diol 
• 921771-00-8 (2R,3R,4R)-2,3-bis(benzyloxy)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopentanone 
• 921770-97-0 (1R,2R,3R,5S)-3-(tert-butyl-dimethylsilanyloxy)-5-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopentane-1,2-diol 
• 921771-06-4 (1S,2R,3R,4S)-2-(benzyloxy)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopentane-1,3-diol 
• 921771-05-3 (4S)-2-(benzyloxy)-4[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopent-2-en-1-one 
• 921770-96-9 tert-butyl-[(1R,4S)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopent-2-en-1-oxy]dimethylsilane 
• 921770-86-7 (4S)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopent-2-en-1-one 

Downstream Products

• 119905-80-5 pseudo-α-D-arabinofuranose 

Relevant academic research and scientific papers

A convenient approach for access to both carbapentofuranoses and carbahexopyranoses. Stereocontrolled synthesis of enantiopure Carba-D-ribofuranoses, Carba-D-arabinofuranoses and Carba-L-gulopyranose

A new approach to carbasugars in enantiomerically pure form is reported. The key step involves ring-closing metathesis of dienols 6 derived from a (R)-(+)-glyceraldehyde derivative 4 to form the substituted cyclopentenol 9 and cyclohexenol 34a. Stereocont

The cobalt-catalyzed oxygenative radical route from hexopyranosides to carbapentofuranoses

Cobalt-catalyzed radical cyclization/oxygenation of various 6-iodohex-1-enitols gave in one step the carbocyclic analogs of pentofuranoses. The reaction was run under very mild conditions and gave moderate to good yields of carbapentofuranoses within a few hours. All the possible 6-iodohex-1-enitol stereoisomers were prepared, and the influence of relative configurations and protecting groups was studied.

A new synthesis of carbapentofuranoses from carbohydrates

Carbafuranosides were synthesized in one step from various O-protected 1,2,6-trideoxy-6-iodo-hex-1-enitols by cobalt catalyzed 5-exo radical-cyclization under molecular oxygen. Yields were fair to good with interesting selectivities.

Cobalt-catalysed radical oxygenation with molecular oxygen

Molecular oxygen is an efficient trap in cobalt-catalysed radical substitution and 5-exo radical cyclization reactions.