29587-01-7

Upstream product

• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 74-88-4 methyl iodide 
• 2595-05-3 Diacetone D-glucose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 3370-81-8 (3R,4R,5R,6R)-6-Hydroxymethyl-4-methoxy-tetrahydro-pyran-2,3,5-triol 
• 949586-03-2 C₂₆H₃₅O₅SiN₃ 
• 949586-02-1 6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-α-D-allofuranose 
• 676342-57-7 6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-β-L-talofuranose 
• 1338971-63-3 C₁₇H₂₄O₅ 
• 18968-51-9 1,2-O-isopropylidene-3-O-methyl-α-D-ribo-pentodialdo-1,4-furanose 
• 1391351-19-1 (R)-methyl 3-((3aR,5R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]-dioxol-5-yl)-3-((R)-2-methoxy-2-phenylacetamido)propanoate 
• 1391351-20-4 (R)-methyl 3-((3aR,5R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]-dioxol-5-yl)-3-((S)-2-methoxy-2-phenylacetamido)propanoate 
• 1391351-21-5 (S)-methyl 3-((3aR,5R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]-dioxol-5-yl)-3-((R)-2-methoxy-2-phenylacetamido)propanoate 
• 1391351-22-6 (S)-methyl 3-((3aR,5R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]-dioxol-5-yl)-3-((S)-2-methoxy-2-phenylacetamido)propanoate 
• 1391351-13-5 methyl (3R)-3-benzylamino-3-[6-methoxy-2,2-dimethyl-(3aR,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]propanoate 
• 1391351-14-6 methyl (3S)-3-benzylamino-3-[6-methoxy-2,2-dimethyl-(3aR,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]propanoate 

Relevant academic research and scientific papers

β-Oxygen effect in the Barton-McCombie deoxygenation reaction: Further experimental and theoretical findings

The chemistry of (S)-methyl xanthates derived from xylo- and ribo-furanose derivatives in the presence of the stannyl radical is investigated. Xanthate derived from β-xylo-furanose affords exclusively a deoxygenated product; whereas, under the same reacti

Design of β-amino acid with backbone-side chain interactions: Stabilization of 14/15-helix in α/β-peptides

A new C-linked carbo-β-amino acid, (R)-β-Caa(r), having a carbohydrate side chain with d-ribo configuration, was prepared from d-glucose by inverting the C-3 stereocenter to introduce constraints/ interactions. From the NMR studies it was inferred that the new monomer may participate in additional electrostatic interactions, facilitating and enhancing novel folds in oligomeric peptides derived from it. The α/β- peptides, synthesized from alternating l-Ala and (R)-β-Caa(r), have shown the presence of 14/15-helix by NMR (in CDCl3, methanol-d3 and CD3CN), CD and MD calculations. The hybrid peptides showed the presence of electrostatic interactions involving the intraresidue amide proton and the C3-OMe, which helped in the stabilization of the NH(i)???CO(i-4) H-bonds and adoption of 14/15-helix. The importance of such additional interactions has been well defined in recent times to stabilize the folding in a variety of peptidic foldamers. These observations suggest and emphasize that the side chain-backbone interactions are crucial in the stabilization of the desired folding propensity. The designed monomer thus enlarges the opportunities for the synthesis of peptides with novel conformations and expands the repertoire of the foldamers.

Synthesis of mycinose from 1,2:5,6-Di-O-isopropylidene-α-D- glucofuranose

A facile synthesis of mycinose from commercially available 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose was developed. A selective and direct reductive debromination of α-hydroxy bromides in a simple NaBH4/EtOH/H2O system was found.

Experimental and computational investigation of the unexpected formation of β-substituted polyoxygenated furans from conveniently functionalized carbohydrates

In the course of our current studies on the reactivity of alkylidenecarbenes, prepared with the trimethylsilylazide/Bu2SnO method, on conveniently functionalized α-cyanomesylates derived from d-allose, d-arabinose, and d-threose, we have observ

Ring-modified analogues and molecular dynamics studies to probe the requirements for fungicidal activities of malayamycin A and its N-nucleoside variants

(Chemical Equation Presented) The importance of functional group orientations and the integrity of the bicyclic perhydrofuran core of malayamycin A and two equally active N-nucleoside analogues as fungicides were investigated. Two analogues 10 and 11, representing a THP-truncated and a bicyclic aza-variant, were synthesized and found to be inactive. Molecular dynamics studies on malayamycin A and analogues were performed to highlight the importance of properly orientating the urea and methyl ether groups.

Alternate approaches to the synthesis of 2'-O-Me nucleosides

Three different approaches to the synthesis of 2'-O-methyl nucleosides starting from the corresponding nucleoside or commercially available 1,2:5,6-di-O-isopropylidene-α-D-allofuranose 1 are described.