115509-85-8

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• 133491-12-0 (3aS,4S,6R,6aR)-6-Methoxymethoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 
• 115384-58-2 6-<(methoxymethoxy)methyl>-2,2-dimethyl-3aβ,5,6α,6aβ-tetrahydro-4H-cyclopenta-1,3-dioxol-4-one 
• 112543-75-6 (3aR,4S,5S,6aS)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 
• 105265-93-8 (3R,4S)-3,4-(isopropylidenedioxy)-1-cyclopentene-1-methanol 
• 105265-92-7 methyl (3R,4S)-3,4-(isopropylidenedioxy)-1-cyclopentene-1-carboxylate 
• 105265-91-6 (3aS,6aS)-4-Acetoxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-5,5-dicarboxylic acid dimethyl ester 
• 195245-42-2 (1R,2R,3R,4R)-1,2,3-tribenzyloxy-4-hydroxymethylcyclopentane 
• 1315589-11-7 ((4S,5R)-1-(2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl))-2-(tetrahydro-pyran-2-yloxymethyl)-prop-2-en-1-ol 
• 1315589-19-5 C₁₄H₂₂O₅ 
• 1315589-21-9 (3aR,6aR)-2,2-dimethyl-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one 
• 1315589-25-3 (3aS,4S,5R,6aR)-2,2-dimethyl-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 1315589-30-0 (3aS,4R,5R,6aR)-2,2-dimethyl-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 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,4R)-2,4-diacetoxy-3-benzyloxy-cyclopentylmethyl ester 

Relevant academic research and scientific papers

A new approach to cyclopentitols using CrCl2 mediated domino reaction and ring closing metathesis. the synthesis of 4a-carba-β-d- arabinofuranose and 4a-carba-β-d-lyxofuranose

An efficient method for the syntheses of cyclopentitols from d-ribose is described using Nozaki-Hiyama-Kishi conditions and ring closing metathesis. In this transformation ω-deoxy-ω-iodo ribofuranoside undergoes reductive elimination in the presence of CrCl2 to give the corresponding olefin-aldehyde, which was trapped by a nucleophile under the same conditions to afford the desired diolefinic species. The ring closing metathesis reaction on the diolefinic species with a Grubbs second generation catalyst produced the required carbocycles.

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.

Total synthesis of both methyl 4a-carba-D-arabinofuranosides.

[reaction: see text] The total synthesis of methyl 4a-carba-alpha-D-arabinofuranoside (1) and methyl 4a-carba-beta-D-arabinofuranoside (2) has been achieved starting from D-mannose (5). Key transformations included a ring-closing metathesis of diene 11 em

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.

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

Transformation of D-Xylose to (1R,2R,3R,4R)-2,3,4-Trihydroxy-1-(hydroxymethyl)cyclopentane, Pseudo-β-D-arabinofuranose

The known 3-O-benzyl-D-xylose was converted into methyl (4S,5R,6R)-4,6,7-triacetoxy-5-benzyloxy-2-(methoxycarbonyl)heptanoate (8) by employing Knoevenagel condensation of 2,4,5-tri-O-acetyl-3-O-benzylaldehydo-D-xylose with dimethyl malonate as a key reaction.O-Deacetylation of 8 and successive glycol cleavage followed by acetylation gave a mixture of (1S,4R,5R,6R)-5-acetoxy-6-benzyloxy-4-methoxycarbonyl-2-oxobicycloheptan-3-one and dimethyl (2R,3R,4S)-2,4-diacetoxy-3-benzyloxy-1,1-cyclopentanedicarboxylate (12), which was converted into 12 exclusively.This enentiomerically pure highly oxyganated cyclopentane dicarboxylate 12 was converted into (3S,4S)-3-benzyloxy-1-(t-butyldiphenylsilyloxymethyl)-4-hydroxy-1-cyclopentene (15) by 1) thermal demethoxycarbonylation accompanied by β-elimination of the acetoxyl group, 2) diisobutylaluminium hydride reduction, and 3) selective protection of thus formed 1-cyclopentene-1-methanol.Pyridinium chlorochromate oxidation of 15 followed by reduction with sodium borohydride gave a 6.4:1 mixture of (3S,4R)-3-benzyloxy-1-(t-butyldiphenylsilyloxymethyl)-4-hydroxy-1-cyclopentene (18) and 15.Hydroboration of O-desilyl derivative of 18 proceeded stereoselectively from the less hindered α-face, and (1R,2R,3R,4R)-2,4-diacetoxy-1-acetoxymethyl-3-(benzyloxy)cyclopentane (21) was obtained after acetylation.Deprotection of 21 gave pseudo-β-D-arabinofuranose.

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