34820-00-3

Upstream product

• 51023-63-3 methyl-α,β-D-mannopyranoside 
• 98-88-4 benzoyl chloride 
• 569329-23-3 Ectyoceramide hexaacetate 
• 97-30-3 methyl D-galactopyranoside 
• 67-56-1 methanol 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 571194-37-1 Ectyoceramide 
• 65236-82-0 1,2-O-(α-methoxybenzylidene)-3,4,6-tri-O-benzoyl-β-D-mannopyranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 1391727-72-2 pent-4-enyl 3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-mannopyranose 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 

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 
• 53182-61-9 methyl 2,3,4-tri-O-benzoyl-β-D-galactopyranoside 
• 1263311-56-3 methyl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranoside 

Relevant academic research and scientific papers

A carbohydrate-anion recognition system in aprotic solvents

A carbohydrate-anion recognition system in nonpolar solvents is reported, in which complexes form at the B-faces of β-D-pyranosides with H1-, H3-, and H5-cis patterns similar to carbohydrate-π interactions. The complexation effect was evaluated for a range of carbohydrate structures; it resulted in either 1:1 carbohydrate-anion complexes, or 1:2 complex formation depending on the protection pattern of the carbohydrate. The interaction was also evaluated with different anions and solvents. In both cases it resulted in significant binding differences. The results indicate that complexation originates from van der Waals interactions or weak CHA- hydrogen bonds between the binding partners and is related to electron-withdrawing groups of the carbohydrates as well as increased hydrogen-bond-accepting capability of the anions. Facial recognition: A carbohydrate-anion recognition system is reported, in which complexes form at the B-faces of β-D-pyranosides with H1-, H3-, and H5-cis patterns similar to carbohydrate-π interactions (see scheme). The interaction was also evaluated with different anions and solvents. In both cases it resulted in significant binding differences.

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.

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.

Synthesis and structure elucidation of benzoylated deoxyfluoropyranosides

Benzoylated deoxyfluoropyranosides have been synthesized, starting with protected, unprotected, or fluorinated precursors. Fluorination of eight derivatives was compared using DAST and Deoxo-Fluor as reagents. Deoxo-Fluor was found to be especially useful

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

Regioselective C-6 hydrolysis of methyl O-benzoyl-pyranosides catalysed by candida rugosa lipase

Hydrolysis of six methyl O-benzoyl-pyranosides has been investigated using Candida rugosa lipase in dioxane/buffer mixtures. The lipase catalysed the hydrolysis of all substrates in a regiospecific manner at C-6, The rate of reaction was dependent on pyra

Antiplasmodial metabolites isolated from the marine octocoral Muricea austera

Bioassay-guided fractionation of the MeOH extract from the octocoral Muricea austera collected in the Pacific coast of Panama led to the isolation of eight compounds, including three tyramine derivatives (1-3), two steroidal pregnane glycosides (4, 5), and three sesquiterpenoids (6-8). Compounds 2-5 are new natural products, and their structures were determined on the basis of their spectroscopic data (HRMS, 1D and 2D NMR, and CD studies). The antiprotozoal activities of the natural compounds 1-8 as well as those of a series of synthetic glycosides (11-22) and tyramine derivatives (23-35) were evaluated in vitro against a drug-resistant Plasmodium falciparum and intracellular form of Trypanosoma cruzi.