113299-31-3

Upstream product

• 129885-83-2 (3aR,6R,6aR)-2,2-Dimethyl-6-trityloxymethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one 
• 128949-31-5 (-)-(1S,2S,3R,4R)-2,3-dihydroxy-2,3-O-isopropylidene-4-hydroxymethylcyclopentan-1-ol 
• 115509-13-2 (3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 
• 129885-79-6 ((1R,4R)-4-Acetoxy-cyclopent-2-enyl)-acetic acid methyl ester 
• 112543-75-6 (3aR,4S,5S,6aS)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 
• 763105-46-0 (S)-(S)-4-(1,4-Dioxa-spiro[4.5]dec-2-yl)-cyclopent-2-enol 
• 921771-04-2 (1S,2S,3R,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-cyclopentanol 
• 305834-30-4 (1S,2S,3R,4R)-3-tert-butyldimethylsilyloxy-4-hydroxymethyl-1,2-O,O-(methylethylidenedioxy)cyclopentane 
• 112543-75-6 (3aR,4R,5R,6aS)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 
• 105265-91-6 (3aS,6aS)-4-Acetoxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-5,5-dicarboxylic acid dimethyl ester 
• 105265-92-7 methyl (3R,4S)-3,4-(isopropylidenedioxy)-1-cyclopentene-1-carboxylate 
• 105265-93-8 (3R,4S)-3,4-(isopropylidenedioxy)-1-cyclopentene-1-methanol 
• 115384-58-2 6-<(methoxymethoxy)methyl>-2,2-dimethyl-3aβ,5,6α,6aβ-tetrahydro-4H-cyclopenta-1,3-dioxol-4-one 
• 133491-12-0 (3aS,4S,6R,6aR)-6-Methoxymethoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 

Relevant academic research and scientific papers

Synthesis of α- and β-D-carbaribofuranose from (+)-norborn-5-en-2-one

α- and β-D-carbaribofuranose 7 and 9, resp., are prepared from ( + )-norborn-5-en-2-one in a 6-step (8-step, resp.) synthetic sequence in 27% (13%, resp.) overall yield.

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.

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.

Synthesis of pseudo-Ribofuranoses by Stereocontrolled Reactions on 4-Hydroxycyclopent-2-enylmethanol Derivatives

The diol 3 is a major product formed from a Prins reaction on cyclopentadiene and was readily converted into the derivatives 4-7.The latter compounds were obtained in states of high optical purity by using both enzyme-catalysed hydrolysis and esterificati

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.

Transformation of D-Erythrose to Some Pseudoaldopentofuranoses. Syntheses of (1S,2R,3S,4S)-, (1R,2R,3S,4S)-, and (1R,2S,3S,4S)-2,3,4-Trihyroxy-1-(hydroxymethyl)cyclopentanes and (1R,2S,3R,4R)-2,3-Dihydroxy-4-(hydroxymethyl)-1-cyclopentanamine

Sodium borohydride reduction of (1S,3S,4S)-1--3,4-(isopropylidenedioxy)-2-cyclopentanone (11), which was prepared from D-erythrose, proceeds exlusively from the β-face to provide 2R-hydroxyl derivative 12.Compound 12 is a derivative of carbocyclic analogue of β-L-lyxofuranose.Silica gel promoted configurational inversion at the branched carbon in 11 followed by sodium borohydride reduction provides 1R,2R diastereomer 17 and 12 a 2.8:1 ratio.The former is a protected form of carboxylic α-D-ribofuranose.Replacement of the mesyloxy group in 23, which was derived from 17, by a hydroxyl group in a SN2 fashion and deprotection of the product followed by acetylation gave a derivative of carbocyclic α-D-xylofuranose 24.Compound 17 was also converted to compound 7, a key intermediate for the synthesis of the carboxylic nucleoside antibiotic (-)-aristeromycin (1), via a SN2 replacement of the mesyloxy group in 26 by an azide group.

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