105265-95-0

Upstream product

• 115384-58-2 6-<(methoxymethoxy)methyl>-2,2-dimethyl-3aβ,5,6α,6aβ-tetrahydro-4H-cyclopenta-1,3-dioxol-4-one 
• 105265-94-9 (1S,2S,3S,4S)-2,3,4-triacetoxy-1-(acetoxymethyl)cyclopentane 
• 112543-75-6 (3aR,4S,5S,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 
• 1410003-58-5 (1S,2R,3S,4S)-1-O-benzyl-4-hydroxymethyl-cyclopentane-1,2,3-triol 
• 1410003-52-9 (1S,2R,3S,4S)-1-O-benzyl-2-O-tert-butyldimethylsilyl-4-vinyl-cyclopentane-1,2,3-triol 
• 384341-72-4 (1S,4R,5S,6S)-5,6-bis-(tert-butyldimethylsilanyloxy)-2-oxabicyclo[2.2.1]heptan-3-one 
• 384341-88-2 (S)-5-[(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydroxy-propyl]-dihydro-furan-2-one 
• 384341-71-3 (2S,2'S)-2-(tert-butyldimethylsilanyloxy)-(5-oxo-tetrahydrofuran-2-yl)acetaldehyde 
• 131530-77-3 (5S)-5-((S)-[((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])dihydrofuran-2-one 
• 127940-36-7 (5R)-5-((S)-[((R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one 
• 127940-37-8 (5S)-5-((S)-[((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one 
• 384341-74-6 (1S,2S,3S,4S)-2,3-di-O-(tert-butyldimethylsilanyl)-4-hydroxymethylcyclopentane-1,2,3-triol 
• 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

Variable strategy toward carbasugars and relatives. 2. Diversity-based synthesis of β-D-xylo, β-D-ribo, β-L-arabino, and β-L-lyxo 4a-carbafuranoses and (4a-carbafuranosyl)thiols

The silyloxy diene-based construction of carbasugars, previously exploited for the synthesis of four carbocyclic furanose and pyranose analogues, has been investigated further. By introducing a novel silylative cycloaldolization protocol and by adjusting a couple of minor transformations, the efficiency of this synthetic sequence was greatly improved. Through a series of lactone/thiolactone aldehyde cyclization precursors, four carbafuranoses (4a-carba-β-D-xylofuranose, 4a-carba-β-D-ribofuranose, 4a-carba-β-L-arabinofuranose, and 4a-carba-β-L-lyxofuranose) and four (carbafuranosyl)thiols [(4a-carba-β-D-xylofuranosyl)thiol, (4a-carba-β-D-ribofuranosyl)thiol, (4a-carba-β-L-arabinofuranosyl)thiol, and (4a-carba-β-L-lyxofuranosyl)thiol] were assembled. From this study, it was shown that these constructions tolerate a variety of precursors, and in many instances, they are suitable for scaling-up.

Synthesis of 4a-carba-β-l-lyxofuranose, 4a-carba-β-l- arabinofuranose and 2,2,5-trimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one using Mn/CrCl3 mediated domino reactions and ring closing metathesis

A common method for the synthesis of 4a-carba-β-l-lyxofuranose and 4a-carba-β-l-arabinofuranose from d-mannose and 2,2,5-trimethyl-3a,6a- dihydro-cyclopenta[1,3]dioxol-4-one from d-ribose is described using catalytic Nozaki-Hiyama-Kishi (NHK) conditions and ring closing metathesis (RCM). In this transformation, ω-deoxy-ω-iodo manno/ribo furanoside undergoes reductive elimination in the presence of Mn/CrCl3 to give the corresponding olefin-aldehyde which was trapped by nucleophile under the same conditions to afford the desired diolefinic species. The ring closing metathesis reaction on these diolefinic species with Grubbs second generation catalyst produced the required carbocycles.

(R)-2,3-O-Cyclohexylideneglyceraldehyde: A useful template for a simple entry into carbafuranose stereoisomers

(R)-2,3-O-Cyclohexylideneglyceraldehyde 1 provides a simple route for the preparation of carbafuranoses. This has been exemplified by the preparation of 10c and 10d, the derivatives of carba d-xylofuranose and carba-l-arabinofuranose respectively, starting from homoallylic alcohol 2a derived from 1. The key step in this protocol was the intramolecular allylation of 9 promoted by several metals under wet conditions that resulted in the construction of the carbafuranose skeleton of 10. The potential of several metals regarding the efficacy and stereoselectivity of this crucial intramolecular allylation reaction has been studied. The moderate stereoselectivity in all of the successful intramolecular allylations of 9 yielding both d-10c and l-10d as the major products contributed significantly in attaining stereo-divergence in this route. The utility of this route was due to the easy availability of 1, and the operational simplicity as well as scalability of all of the reactions involved.

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.

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

A NEW TRANSFORMATION OF ALDOSE DERIVED SYNTHONS TO PSEUDO-HEXOPYRANOSE OR PSEUDO-PENTOFURANOSE DERIVATIVES

The D-ribose or D-erythrose derived acyclic synthon, which possesses a 2-malonyl carbon chain at C-1 position, was cyclized stereoselectively to a six- or five-membered carbocycle.Those carbocycles were converted into pseudo-β-L-mannopyranose derivatives