144938-80-7

Usage

Structure

Cyclopentane-based compound with three hydroxyl groups and a hydroxymethyl group

Explanation

The compound is based on a cyclopentane ring, which is a five-membered ring of carbon atoms. It has three hydroxyl (OH) groups and one hydroxymethyl (CH2OH) group attached to the ring.

Explanation

The stereochemistry of the compound is described by the (1S,2R,3S,4S) designation, which indicates the orientation of the substituents on the cyclopentane ring. The "S" and "R" notations represent the absolute configuration of the chiral centers (carbon atoms with four different substituents) in the molecule.

Explanation

Due to its unique structure and reactivity, 1,2,3-Cyclopentanetriol, 4-(hydroxymethyl)-, (1S,2R,3S,4S)can be used in various fields, such as organic synthesis to create new compounds, and in medicinal chemistry to develop new drugs. It may also have uses in the pharmaceutical, agrochemical, and other industrial sectors.

Explanation

The compound's reactivity is influenced by its specific structure, which includes the cyclopentane ring and the hydroxyl and hydroxymethyl groups. This unique reactivity makes it a valuable compound for various applications in the fields mentioned above.

Stereochemistry

(1S,2R,3S,4S)

Potential Applications

Organic synthesis, medicinal chemistry, pharmaceuticals, agrochemicals, and other industrial applications

Reactivity

Unique reactivity due to its structure

Upstream product

• 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 
• 144938-84-1 (1S,2R,3S,4S)-(+)-1,2,3-Triacetoxy-4-(acetoxymethyl)cyclopentane 
• 175844-96-9 2,3,4-Tri-O-benzyl-5,6-dideoxy-L-arabino-hex-5-enose 
• 305834-23-5 3,4,5-tri-O-benzyl-1,2-dideoxy-L-lyxo-hex-1-enitol 
• 195245-31-9 3,4,5-tri-O-benzyl-1,2,6-trideoxy-6-iodo-L-lyxo-hex-1-enitol 
• 144938-81-8 (3S,5R)-(+)-3-(tert-Butyldimethylsiloxy)-5-(tert-butyldimethylsiloxymethyl)cyclopentene 
• 144938-82-9 (1S,4R)-(+)-4-(Hydroxymethyl)cyclopent-2-enol 
• 305834-18-8 (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-(iodomethyl)-6-methoxytetrahydro-2H-pyran 
• 4356-80-3 methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 
• 763105-43-7 (R)-(S)-5-(1,4-Dioxa-spiro[4.5]dec-2-yl)-hepta-1,6-dien-3-ol 
• 921771-21-3 (S)-1-((1S,2S,3R,4S)-2,3,4-Tris-benzyloxy-cyclopentyl)-ethane-1,2-diol 
• 921770-92-5 (1S,2S,3S,5R)-3-(benzyloxy)-5-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]cyclopentane-1,2-diol 
• 921770-95-8 (1R,2S,3R,4S)-2,3,4-Tris-benzyloxy-cyclopentanecarbaldehyde 

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.

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.

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