30253-76-0

Upstream product

• 100-51-6 benzyl alcohol 
• 4692-12-0 1,3,4,6-tetra-O-acetyl glucopyranose 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 52579-97-2 1,6-anhydro-3,4-O-isopropylidene-β-D-galactopyranose 
• 100-39-0 benzyl bromide 
• 55287-62-2 O²-benzyl-O³,O⁴-isopropyliden-1,6-anhydro-β-D-galactopyranose 
• 76375-66-1 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 55735-75-6 methyl 3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranoside 
• 53958-32-0 methyl α-D-glucopyranoside 2-benzyl ether 
• 15038-71-8 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 2280-44-6 D-Glucose 

Downstream Products

• 53872-78-9 3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-galactopyranosyl bromide 
• 791611-44-4 Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-acetylamino-octadecyloxy)-tetrahydro-pyran-4-yl ester 
• 791611-45-5 Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-octanoylamino-octadecyloxy)-tetrahydro-pyran-4-yl ester 
• 791611-41-1 Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-hexyloxy)-tetrahydro-pyran-4-yl ester 
• 791611-42-2 Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-nonyloxy)-tetrahydro-pyran-4-yl ester 
• 791611-46-6 Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-hexadecanoylamino-octadecyloxy)-tetrahydro-pyran-4-yl ester 
• 791611-43-3 Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-tridecyloxy)-tetrahydro-pyran-4-yl ester 
• 79705-36-5 Benzyl-2,3-O-isopropyliden-4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl)-α-L-rhamnopyranosid 
• 79705-41-2 Benzyl-4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl)-α-L-rhamnopyranosid 
• 79705-33-2 (2,2,2-Trichlorethyl)-2,3-O-isopropyliden-4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl)-α-L-rhamnopyranosid 
• 79705-42-3 Benzyl-4-0-(2-O-benzyl-α-D-galactopyranosyl)-α-L-rhamnopyranosid 
• 55287-66-6 Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-2-acetoxymethyl-5-benzyloxy-6-chloro-tetrahydro-pyran-3-yl ester 
• 190970-17-3 C₇₀H₇₁N₅O₁₅ 
• 177412-85-0 N-(9-{(2R,3R,4S,5R)-4-{(2R,3R,4S,5S,6R)-3-Benzyloxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide 

Relevant academic research and scientific papers

Corrected order in the simultaneous debenzylation-acetolysis of methyl 2,3,4,6-tetra-O-benzyl-α-d-glucopyranoside

The benzyl groups of methyl 2,3,4,6-tetra-O-benzyl-α-d-glucopyranoside were cleaved in the order of 6-O-Bn > 3-O-Bn > 4-O-Bn > 2-O-Bn under acid-mediated conditions in acetic anhydride. The order is a correction of that previously reported.

To acetyl cedilanid glucose modified compound liposomes and the use thereof (by machine translation)

The invention discloses a de-acetyl cedilanid glucose modified compound liposome and its application. Mainly from the cedilanid glucose-based reconstruction, to glucose and 2 - amino glucose as raw material for some molecular modification with the end of the digoxin 3 - hydroxyl at the delivery into connected to acetyl cedilanid glucose-based modified product, in active under the guide of the choose to conform with the requirements of the molecule. By synthesis to acetylation cedilanid glucose modified compounds (2 - O - benzyl - β - D - glucopyranoside - acetyl cedilanid and the like), so as to enhance the anti-cancer effect of such compounds, improve the strength of the titer, prolong the half-life, at the same time the modified compound preparation into the liposome, improve the targeting [...], reduce cardiac toxicity. (by machine translation)

Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine

We report a synthetic glycosylation reaction between sucrosyl acceptors and glycosyl fluoride donors to yield the derived trisaccharides. This reaction proceeds at room temperature in an aqueous solvent mixture. Calcium salts and a tertiary amine base promote the reaction with high site-selectivity for either the 3′-position or 1′-position of the fructofuranoside unit. Because nonenzymatic aqueous oligosaccharide syntheses are underdeveloped, mechanistic studies were carried out in order to identify the origin of the selectivity, which we hypothesized was related to the structure of the hydroxyl group array in sucrose. The solution conformation of various monodeoxysucrose analogs revealed the co-operative nature of the hydroxyl groups in mediating both this aqueous glycosyl bond-forming reaction and the site-selectivity at the same time.

Effects of lipid chain lengths in α-galactosylceramides on cytokine release by natural killer T cells

Glycolipid presentation by CD1 proteins has emerged as an important aspect of antigen recognition, and presentation of α-glycosylceramides by CD1d to natural killer T cells has become a central focus in understanding how glycolipid presentation can influence immune responses. An α-galactosylceramide containing relatively long lipid chains has been the subject of intense study because, when presented by CD1d to natural killer T cells, it stimulates the release of both proinflammatory and immunomodulatory cytokines. Using an efficient synthesis of α-galactosylceramides, we have prepared a series of glycolipids in which the lipid chain lengths have been incrementally varied. The responses of natural killer T cells to these glycolipids have been determined, and we have found that truncation of the phytosphingosine lipid chain increases the relative amounts of immunomodulatory cytokines released. In similar fashion, the length of the acyl chain in α-galactosylceramides influences cytokine release profiles. Copyright

Regio- and stereoselective synthesis of β-D-gluco-, α-L-ido-, and α- L-altropyranosiduronic acids from Δa4-uronates

The stereoselective synthesis of β-D-glucopyranosiduronic, α-L- idopyranosiduronic, and α-L-altropyranosiduronic acids has been performed from different Δ4-uronate monosaccharides. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives, which were converted to the corresponding epoxides in high yields. Direct reduction of the epoxides using boranetetrahydrofuran complex led to the corresponding glucuronic acids in low to good yields. Glucuronic acids were also obtained in satisfactory yields through a two-steps procedure involving bromination of the epoxide with titanium(IV) bromide followed by reduction using tributyltin hydride. Lewis acid-catalyzed rearrangement of these epoxides led to the corresponding α-L C-4 ketopyranosides adopting the 1C4 chair conformation. Hydride reduction afforded the α-L-idopyranosiduronic or the α-L- altropyranosiduronic acids, the stereoselectivity of the reduction being controlled by the appropriate substitution pattern.

Syntheses and 1H- and 13C-Nuclear Magnetic Resonance Spectra of All Positional Isomers of Tetra-O-acetyl-D-glucopyranoses, and Their Monobenzyl and Monotrityl Derivatives

All the isomers of the tetra-O-acetyl-D-glucopyranoses, and their monobenzyl and monotrityl derivatives were synthesized and systematic 1H- and 13C-nuclear magnetic resonance (1H- and 13C-NMR) studies were carried out.Complete assignments of the 1H- and 13C-NMR signals were achieved by 1H- and 13C-decoupling techniques and by the use of a shift reagent and changes of solvents.Moreover, when necessary, 1H- and 13C-shift-correlated 2D NMR spectroscopy at higher frequency (Bruker AM 400) was applied.The shifts on deacetylation, benzylation, and tritylation were estimated on the basis of the 1H- and 13C-chemical shifts of these compounds, and the effects of deacetylation and benzyl- or trityl-substitution are discussed.Keywords - tetra-O-acetyl-D-glucopyranose; monobenzyl tetra-O-acetyl-D-glucopyranose; monotrityl tetra-O-acetyl-D-glucopyranose; 1H-NMR; 13C-NMR; deacetylation shift; benzylation shift; tritylation shift