149342-31-4

Basic information

• Product Name: 2,3:5,6-di-O-isopropylidene-D-mannofuranose
• CAS NO: 149342-31-4
• Molecular Weight: 260.287
• Mol File: 149342-31-4.mol
• Article Data: 57

Chemical Properties

• CAS DataBase Reference: 2,3:5,6-di-O-isopropylidene-D-mannofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3:5,6-di-O-isopropylidene-D-mannofuranose(149342-31-4)
• EPA Substance Registry System: 2,3:5,6-di-O-isopropylidene-D-mannofuranose(149342-31-4)

Safety Data

• Hazardous Substances Data: 149342-31-4(Hazardous Substances Data)

Upstream product

• 3458-28-4 D-Mannose 
• 77-76-9 2,2-dimethoxy-propane 
• 530-26-7 D-Mannose 
• 75-52-5 nitromethane 
• 5328-37-0 L-arabinose 
• 67-64-1 acetone 
• 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 
• 116-11-0 2-Methoxypropene 
• 582-52-5 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 76679-45-3 Benzyl-2,3-di-O-benzyl-5-O-(2,3:5,6-di-O-isopropyliden-β-D-mannofuranosyl)-β-D-ribofuranosid 
• 76679-42-0 Benzyl-2,3-di-O-benzyl-5-O-(2,3:5,6-di-O-isopropyliden-α-D-mannofuranosyl)-β-D-ribofuranosid 
• 17087-84-2 (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 
• 94898-41-6 (3aS,4R,6R,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole 
• 79241-07-9 (R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan 
• 7306-64-1 2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone 
• 54469-08-8 benzyl 2,3:5,6-di-O-isopropylidene-β-D-mannofuranoside 
• 54469-08-8 phenylmethyl 2,3:5,6-di-O-(1-methylethylidene)-α-D-mannofuranoside 
• 135902-10-2 N-benzhydrylmannofuranosylamine 2,3:5,6-diacetonide 
• 181173-63-7 (3aS,4R,6R,6aS)-4-(3-Benzyloxy-2-tetradecyloxy-propoxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole 
• 181173-64-8 (3aS,4R,6R,6aS)-4-(3-Benzyloxy-2-hexadecyloxy-propoxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole 
• 181173-66-0 (3aS,4S,6R,6aS)-4-(3-Benzyloxy-2-hexadecyloxy-propoxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole 
• 181173-65-9 (3aS,4R,6R,6aS)-4-(3-Benzyloxy-2-octadecyloxy-propoxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole 
• 181173-67-1 (3aS,4S,6R,6aS)-4-(3-Benzyloxy-2-octadecyloxy-propoxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole 

Relevant articles and documents

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 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.

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.

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.

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).

First synthesis of P-aryl-phosphinosugars, organophosphorus analogues of C-arylglycosides

The synthesis and X-ray crystal structure of the first example of arylphosphinosugar are reported. The protected polyhydroxylated 1,2-oxaphosphinane is prepared by a two steps sequence (phenylphosphinate addition on protected mannofuranose followed by int

Straightforward synthesis of protected 2-hydroxyglycals by chlorination-dehydrochlorination of carbohydrate hemiacetals

A straightforward and scalable method for the synthesis of protected 2-hydroxyglycals is described. The approach is based on the chlorination of carbohydrate-derived hemiacetals, followed by an elimination reaction to establish the glycal moiety. 1,2-dehy