119905-80-5

Upstream product

• 133491-12-0 (3aS,4S,6R,6aR)-6-Methoxymethoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 
• 112543-75-6 (3aR,4S,5S,6aS)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 
• 921770-99-2 (1R,2S,3R,4R)-2,3-bis(benzyloxy)-4-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopentanol 
• 73111-16-7 3,4,5-tri-O-benzyl-1,2-dideoxy-L-xylo-hex-1-enitol 
• 115384-58-2 6-<(methoxymethoxy)methyl>-2,2-dimethyl-3aβ,5,6α,6aβ-tetrahydro-4H-cyclopenta-1,3-dioxol-4-one 
• 105265-93-8 (3R,4S)-3,4-(isopropylidenedioxy)-1-cyclopentene-1-methanol 
• 119826-17-4 Benzoic acid (1R,2R,3R)-3-benzyloxy-2-formyloxy-4-hydroxy-5-nitro-cyclopentylmethyl ester 
• 119826-19-6 Benzoic acid (1R,2R,3R,4S)-2,4-diacetoxy-3-benzyloxy-cyclopentylmethyl ester 
• 119826-16-3 Benzoic acid (2R,3R,4S)-4-benzyloxy-3-formyloxy-2-nitromethyl-5-oxo-pentyl ester 
• 4594-60-9 methyl 3,4-O-isopropylidene-β-D-arabinopyranoside 
• 5328-63-2 methyl-β-D-arabinopyranoside 
• 1053720-20-9 Acetic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-methoxy-3-nitromethyl-tetrahydro-pyran-3-yl ester 
• 149454-94-4 C₂₈H₄₀O₆ 
• 149454-91-1 (3R,4S,5S,6R)-4,5-Bis-benzyloxy-6-methoxy-3-nitromethyl-tetrahydro-pyran-3-ol 

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.

Cobalt-catalysed radical oxygenation with molecular oxygen

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

Samarium(II) Iodide Promoted Ring Contraction of Carbohydrate Derivatives: an Expeditious Synthesis of Functionalised Cyclopentanes

Aldehydo methyl pyranosides undergo ring contraction induced by treatment with samarium(ii) iodide, in the presence of HMPA and tert-butyl alcohol, to give highly functionalised cyclopentanes.

Synthesis of all stereoisomeric carbapentofuranoses

All carbocyclic analogs of the pentofuranoses were synthesized starting from norborn-5-en-2-one (1). By using either base- or acid-catalyzed Baeyer- Villiger reaction of 1, the central intermediates 2 and 3 were obtained. The required functionalization of the olefinic double bond was achieved either by cis-hydroxylation in the case of the ribo, lyxo, and α-xylo derivatives or by epoxidation and subsequent opening with aqueous perchloric acid. In the latter case, a pronounced selectivity for opening the epoxy alcohol in the 3- position was found. I an epoxy acetate with both functions on the same side of the ring was used, the eposide was opened in the 2-position by neighboring group participation of the acetate. The requisite side chain degradation was accomplished either by conversion of the ester into an olefin and subsequent dihydroxylation/cleavage reaction or by Curtius rearrangement to the amine and its conversion into an acetate.

Facile syntheses of pseudo-α-D-arabinofuranose, and two pseudo-D-arabinofuranosylnucleosides, (+)-cyclaradine and (+)-1-pseudo-β-D-arabinofuranosyluracil, from D-arabinose

An optically active pseudo-sugar, pseudo-α-D-arabinofuranose, was efficiently synthesized from D-arabinose by using a stereoselective nitromethane addition reaction to form a branched nitropyranose (6) as a key step. Furthermore, two biologically active p

A new approach to the synthesis of optically active pseudo-sugar and pseudo-nucleoside - Syntheses of pseudo-α-D-arabinofuranose, (+)-cyclaradine, and (+)-1-pseudo-β-D-arabinofuranosyluracil from D-arabinose

An optically active pseudo-sugar, pseudo-α-D-arabinofuranose, was synthesized from D-arabinose in favorable overall yield by using a stereoselective formation of branched nitropyranose as the key step. Furthermore, two biologically active pseudo-β-D-arabi

BIOSYNTHESIS OF ARISTEROMYCIN: EVIDENCE FOR THE INTERMEDIACY OF A 4β-HYDROXYMETHYL-1α,2α,3α-TRIHYDROXYCYCLOPENTANETRIOL.

Evidence for the intermediacy of a 4β-hydroxymethyl-1α,2α,3α-trihydroxycyclopentanetriol (5 or 6) in the biosynthesis of the nucleoside antibiotic aristeromycin (1) has been obtained by administration of doubly-labeled forms of D-glucose to the fermentation broth of Streptomyces citricolor followed by trapping of the tetrol 5 using isotope dilution methods.

SYNTHESES OF PSEUDO-α-D-ARABINOFURANOSE, PSEUDO-β-D-ARABINOFURANOSE, AND PSEUDO-β-L-XYLOFURANOSE, THREE OPTICALLY ACTIVE PSEUDO-PENTOFURANOSES, FROM D-GLUCOSE

Using lead tetraacetate oxidation and cyclitol formation with KF in the presence of 18-crown-6 as key reactions, three optically active pseudo-pentofuranoses: pseudo-α-D-arabinofuranose, pseudo-β-D-arabinofuranose,and pseudo-β-L-xylofuranose, have been sy

A Novel Transformation of Four Aldoses to Some Optically Pure Pseudohexopyranoses and a Pseudopentofuranose, Carboxylic Analogues of Hexopyranoses and Pentofuranose. Synthesis of Derivatives of (1S,2S,3R,4S,5S)-, (1S,2S,3R,4R,5S)-, (1R,2R,3R,4R,5S)-, (1S,

Knoevenagel reactions with dimethyl malonate of the suitably protected acylic aldehydes 6, 20, 34, and 46, which were prepared from D-ribose, D-xylose, D-arabinose, and D-erythrose, respectively, proceeded smoothly to provide α,β-unsaturated diesters 7, 2