149342-31-4

Upstream product

• 3458-28-4 D-Mannose 
• 77-76-9 2,2-dimethoxy-propane 
• 67-64-1 acetone 
• 530-26-7 D-Mannose 
• 582-52-5 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 
• 116-11-0 2-Methoxypropene 
• 75-52-5 nitromethane 
• 5328-37-0 L-arabinose 
• 49561-21-9 (3aR,6S,6aR)-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 
• 7306-64-1 2,3:5,6-di-O-isopropylidene-L-gulonolactone 
• 1128-23-0 L-gulono-1,4-lactone 
• 50-81-7 ascorbic acid 

Downstream Products

• 138034-65-8 (1R)-2,3-5,6-di-O-isopropylidene-1-C-phenyl-D-mannitol 
• 138034-65-8 (R)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)((4S,5R)-5-((S)-hydroxy (phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol 
• 7306-64-1 2,3:5,6-di-O-isopropylidene-α-D-mannono-1,4-lactone 
• 157309-47-2 Acetic acid (R)-[(4R,5R)-5-((1R,2R)-1-acetoxy-2,3-dihydroxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-phenyl-methyl ester 
• 157309-46-1 Acetic acid (R)-[(4R,5R)-5-((R)-acetoxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester 
• 162808-23-3 (3aS,4R,6S,6aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxole 
• 157309-48-3 (Z)-(R)-4-Acetoxy-4-[(4S,5R)-5-((R)-acetoxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-but-2-enoic acid methyl ester 
• 126797-24-8 benzyl (D-manno-2,3,4,5,6-pentahydroxyhexyl)phosphinicoformate 
• 126797-23-7 (2S)-2-benzyloxycarbonyl-6-(1',2'-dihydroxyethyl)-4,5-dihydroxy-4,5:1',2'-di-O-isopropylidene-D-manno-1,2λ⁵-oxaphosphorinan-2-one 
• 126797-17-9 (2S)-6-(1',2'-dihydroxyethyl)-4,5-dihydroxy-4,5:1',2'-di-O-isopropylidene-2-phenylthio-D-manno-1,2λ⁵-oxaphosphorinan-2-one 
• 126797-17-9 (2R)-6-(1',2'-dihydroxyethyl)-4,5-dihydroxy-4,5:1',2'-di-O-isopropylidene-2-phenylthio-D-manno-1,2λ⁵-oxaphosphorinan-2-one 
• 82300-71-8 (3aS,4R,6R,6aR)-4-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-(2,4,6-trimethoxy-phenyl)-tetrahydro-furo[3,4-d][1,3]dioxole 
• 6160-67-4 (3aS,4R,6R,6aS)-4-chloro-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 76679-45-3 Benzyl-2,3-di-O-benzyl-5-O-(2,3:5,6-di-O-isopropyliden-β-D-mannofuranosyl)-β-D-ribofuranosid 

Relevant academic research and scientific papers

Kiliani on ketoses: Branched carbohydrate building blocks from D-fructose and L-sorbose

Protected branched sugar lactones are available via Kiliani-acetonation sequences on readily available ketoses such as d-fructose and l-sorbose. In both cases, the readily crystallized diacetonides have a 2,3-cis-diol relationship in the product lactone. An efficient double inversion of the configuration at C-4 and C-5 of the product from d-fructose gives access to the formal Kiliani product from l-psicose. Branched carbohydrate lactones are likely to be of significant value as chirons for homochiral targets with functionalized quaternary centres.

Synthesis of 3-deoxy-2-ulosonic acid KDO and 4-epi-KDN, a highly efficient approach of 3-C homologation by propargylation and oxidation

Through the introduction of a pyruvate segment by asymmetric propargylation and oxidation of terminal alkynes, both KDO and 4-epi-KDN have been concisely synthesized in the furanose form from readily available sugars in high overall yields.

Synthesis of Galactosyl-Queuosine and Distribution of Hypermodified Q-Nucleosides in Mouse Tissues

Queuosine (Q) is a hypermodified RNA nucleoside that is found in tRNAHis, tRNAAsn, tRNATyr, and tRNAAsp. It is located at the wobble position of the tRNA anticodon loop, where it can interact with U as well as C bases located at the respective position of the corresponding mRNA codons. In tRNATyr and tRNAAsp of higher eukaryotes, including humans, the Q base is for yet unknown reasons further modified by the addition of a galactose and a mannose sugar, respectively. The reason for this additional modification, and how the sugar modification is orchestrated with Q formation and insertion, is unknown. Here, we report a total synthesis of the hypermodified nucleoside galactosyl-queuosine (galQ). The availability of the compound enabled us to study the absolute levels of the Q-family nucleosides in six different organs of newborn and adult mice, and also in human cytosolic tRNA. Our synthesis now paves the way to a more detailed analysis of the biological function of the Q-nucleoside family.

Enantiomerically pure 3-hydroxypropyl diisopropylidene mannose derivatives

Enantiomerically pure 3-hydroxypropyl diisopropylidene mannose derivatives were prepared and fully characterized. The procedure is generally applicable to monosaccharides and thus facilitates access to differently substituted glycosidic precursors.

Synthesis of oxylipin mimics and their antifungal activity against the citrus postharvest pathogens

Nine oxylipin mimics were designed and synthesized starting from D-mannose. Their antifungal activity against three citrus postharvest pathogens was evaluated by spore germination assay. The results indicated that all the compounds significantly inhibited the growth of Penicillium digitatum, Penicillium italicum and Aspergillus Niger. The compound (3Z,6Z,8S,9R,10R)-octadeca-3,6-diene-8,9,10-triol (3) exhibited excellent inhibitory effect on both Penicillium digitatum (IC50 = 34 ppm) and Penicillium italicum (IC50 = 94 ppm). Their in vivo antifungal activities against citrus postharvest blue mold were tested with fruit inoculated with the pathogen Penicillium italicum. The compound (3R,4S)-methyl 3,4-dihydroxy-5-octyltetrahydrofuran-2-carboxylate (9) demonstrated significant efficacy by reducing the disease severity to 60%. The antifungal mechanism of these oxylipin mimics was postulated in which both inhibition of pathogenic mycelium and stimuli of the host oxylipin-mediated defense response played important roles.

Discovery and Structure-Activity Relationships of Novel Template, Truncated 1′-Homologated Adenosine Derivatives as Pure Dual PPARγ/δModulators

Following our report that A3 adenosine receptor (AR) antagonist 1 exhibited a polypharmacological profile as a dual modulator of peroxisome proliferator-activated receptor (PPAR)γ/δ, we discovered a new template, 1′-homologated adenosine analogues 4a-4t, as dual PPARγ/δmodulators without AR binding. Removal of binding affinity to A3AR was achieved by 1′-homologation, and PPARγ/δdual modulation was derived from the structural similarity between the target nucleosides and PPAR modulator drug, rosiglitazone. All the final nucleosides were devoid of AR-binding affinity and exhibited high binding affinities to PPARγ/δbut lacked PPARα binding. 2-Cl derivatives exhibited dual receptor-binding affinity to PPARγ/δ, which was absent for the corresponding 2-H derivatives. 2-Propynyl substitution prevented PPARδ-binding affinity but preserved PPARγaffinity, indicating that the C2 position defines a pharmacophore for selective PPARγligand designs. PPARγ/δdual modulators functioning as both PPARγpartial agonists and PPARδantagonists promoted adiponectin production, suggesting their therapeutic potential against hypoadiponectinemia-associated cancer and metabolic diseases.

Practical preparation of mono- and di-O-isopropylidene derivatives of monosaccharides and methyl 4,6-O-benzylidene glycosides from free sugars in a deep eutectic solvent

Free sugars were rapidly converted into the corresponding di-O-isopropylidene derivatives and methyl O-benzylidene glycosides in excellent yields and purity in a deep eutectic solvent made from choline chloride and malonic acid (ChCl:MA). Reaction conditions were mild; work-up was easy, and further purification was not necessary. Given the inexpensive, nontoxic, and recyclable nature of ChCl:MA, this protocol is environmental friendly.

Lead tetraacetate mediated one pot oxidative cleavage and acetylation reaction: an approach to apio and homologated apio pyrimidine nucleosides and their anticancer activity

An efficient and versatile strategy of general applicability towards apio and homologated apio pyrimidines has been delineated. The methodology shows tosylation followed by in situ cyclization and one pot oxidative cleavage and acetylation by Pb(OAc)4 as the key steps. The methodology has been applied to d-ribose and d-mannose derivatives to achieve asymmetric synthesis of apio and homologated apio pyrimidine nucleosides.

Click Inspired Synthesis of 1,2,3-Triazole-linked 1,3,4-Oxadiazole Glycoconjugates

The glycoconjugation of biologically privileged 1,3,4-oxadiazole scaffold is described via Cu(I)-catalyzed azide–alkyne cycloaddition. A series of glycosyl alkynes 1b–i, obtained from various commercial sugars, were treated with azide functionalized 1,3,4-oxadiazole using click chemistry to access triazole-linked glycosylated 1,3,4-oxadiazoles 10b–i in good yields. The structure of the developed glycoconjugates has been ascertained by extensive spectroscopic analysis (1H &13C NMR, IR, and MS).

A simple and convenient synthetic protocol for O-isopropylidenation of sugars using bromodimethylsulfonium bromide (BDMS) as a catalyst

Various O-isopropylidene derivatives of sugars and acyclic sugars were obtained in very good yields on reaction with acetone at room temperature with a catalytic amount of bromodimethylsulfonium bromide (BDMS). These O-isopropylidene derivatives can also be prepared in good yields on reaction with 2,2-dimethoxypropane (DMP) in acetonitrile using the same catalyst in shorter reaction times. Some of the advantages of this method are high effectiveness, a nonaqueous workup procedure, economic viability, and good yields.