6605-40-9

Usage

InChI:InChI=1/C35H30O10/c1-40-35-30(45-34(39)26-20-12-5-13-21-26)29(44-33(38)25-18-10-4-11-19-25)28(43-32(37)24-16-8-3-9-17-24)27(42-35)22-41-31(36)23-14-6-2-7-15-23/h2-21,27-30,35H,22H2,1H3

Upstream product

• 14218-11-2 2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide 
• 67-56-1 methanol 
• 98-88-4 benzoyl chloride 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-mannopyranose 
• 51023-63-3 methyl-α,β-D-mannopyranoside 
• 15067-04-6 (2R,3R,4S,5R,6R)-2-chloro-6-(benzoyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 23600-19-3 methyl 3-O-tosyl-β-D-glucopyranoside 
• 102518-21-8 methyl 2,3-di-O-benzoyl-β-D-glucopyranoside 
• 172847-85-7 (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 
• 2280-44-6 D-Glucose 
• 97-30-3 methyl D-glucopyranoside 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 

Downstream Products

• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside 
• 3396-68-7 methyl 2,3,6-tri-O-benzoyl-α-D-mannopyranoside 
• 80245-08-5 methyl 3,4,6-tri-O-benzoyl-α-D-mannopyranoside 
• 14315-85-6 methyl 3, 6-di-O-benzoyl-α-D-mannopyranoside 
• 34234-44-1 methyl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside 
• 32849-03-9 methyl 2,3,4,6-tetra-O-benzoyl-α-D-glycopyranoside 
• 80245-09-6 methyl 4,6-di-O-benzoyl-β-D-glucopyranoside 
• 76514-09-5 2,3,4,6-tetra-O-benzoyl-2-bromo-D-glucono-1,5-lactone 
• 53942-33-9 (+)-(5S,6R)-3,5-Bis(benzoyloxy)-6-(benzoyloxymethyl)-5,6-dihydro-2H-pyran-2-one 

Relevant academic research and scientific papers

Carbon tetrachloride-free allylic halogenation-mediated glycosylations of allyl glycosides

The allylic bromination of allyl glycosides is conducted using NBS/AIBN reagents in (EtO)2CO and PhCF3 solutions, without using CCl4 as a solvent. The activated mixed halo-allyl glycosides led to glycosylations, mediated by a triflate, in a latent-active

Chemical constituents of the aerial parts of Algerian Galium brunneum: Isolation of new hydroperoxy sterol glucosyl derivatives

The liposoluble extract of Galium brunneum aerial parts from North-eastern Algeria was chemically investigated. The EtOAc soluble portion contained a series of glycosyl cucurbitacins and sterols including three new glucosyl hydroperoxy sterols 1–3 among other phenolic components whereas the BuOH soluble fraction was dominated by glycosyl derivatives of flavonoids, iridoids and lignans, according to the chemistry reported in the literature for the genus Galium. The structure of new oxidized sterols 1–3 was determined by spectroscopic methods as well as by comparison with related known metabolites. Selected main compounds from both extracts, which revealed moderate antibacterial activities, were tested for their growth inhibitory properties against Gram-positive and Gram-negative bacteria. This is the first report of cucurbitacins in plants of genus Galium.

Direct dehydrative glycosylation catalyzed by diphenylammonium triflate

Methods for direct dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.

Blurring the boundary between bio- and geohopanoids: Plakohopanoid, a C32 biohopanoid ester from Plakortis cf. lita

Plakohopanoid (3a), a new type of hopanoid derivative composed of a C 32 hopanoid acid ester linked to a mannosyl-myo-inositol, was isolated from the sponge Plakortis cf. lita as its peracetyl derivative 3b. The structure of 3b was determined by a combination of spectroscopic analysis and micro-scale chemical degradation. Even though plakohopanoid was isolated from a sponge, its component parts are clearly of bacterial origin, and its bacterial biosynthesis is very likely. Until now, C32 hopanoic acids have been considered to be geohopanoids, i.e., diagenetic products that are formed through abiotic degradation of the biohopanoids present in bacteria. The presence of 3a in a marine living organism shows that there is a biosynthetic pathway to C32 hopanoic acids, and these substances should therefore no longer with certainty be considered to be geohopanoids. Copyright

Methyl 1,2-orthoesters as useful glycosyl donors in glycosylation reactions: A comparison with n-pent-4-enyl 1,2-orthoesters

Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and -benzoates (R = Ph) can function as glycosyl donors - upon BF3·Et 2O activation in CH2Cl2 - in glycosylation reactions with monosaccharide acceptors to afford disaccharides in good yields. In the process, glycosylation is preferred to acid-catalyzed rearrangement leading to methyl mannopyranosides. Methyl 1,2-orthoesters can be also used in regioselective glycosylation protocols with monosaccharide diols, in which they display good regioselectivity. Copyright

Unexpected stereocontrolled access to 1α,1′β-disaccharides from methyl 1,2-ortho esters

Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1α,1′β-disaccharides, upon treatment with BF 3?Et2O in CH2Cl2, rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.

Neurosporaside, a tetraglycosylated sphingolipid from neurospora crassa

The new tetraglycosylceramide neurosporaside (1a) has been isolated from the fungus Neurospora crassa. Neurosporaside is a tetraglycosylated glycosphingolipid characterized by a sugar chain unprecedented among natural glycoconjugates. The structure of neurosporaside was elucidated by extensive spectroscopic analysis and microscale degradation analysis, which allowed full structure elucidation using less than 1 mg of compound.

Indium(III) triflate-mediated one-step preparation of glycosyl halides from free sugars

In(OTf)3 has been found to be an efficient catalyst for the direct conversion of reducing sugars to their respective acylated glycosyl halides in good yields under mild conditions. The glycosyl halides so obtained can be converted to alkyl glyc

Amphiceramide A and B, novel glycosphingolipids from the marine sponge Amphimedon compressed

Glycolipid analysis of the Caribbean sponge Amphimedon compressa has shown it to contain two novel glycosphingoli- pids, amphiceramide A (1a) andB(2a), which possess an unusual A6-phytosphingosine. The saccharide chain of amphiceramide A is composed of a

1 Hand 13C NMR data of methyl tetra-O-benzoyl-D- pyranosides in acetone-d6

Complete assignments of 1H- and 13C-NMR resonances of five methyl tetra-O-benzoyl-D-pyranosides based on 1H, 13C, 2D DQF-COSY, HMQC, HMBC and HSQC-TOCSY experiments have been performed. Copyright