185754-26-1

Upstream product

• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 3396-99-4 methyl α-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 123-11-5 4-methoxy-benzaldehyde 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 273397-25-4 methyl 2,3-di-O-benzoyl-4,6-O-(4-methoxybenzylidene)-α-D-galactopyranoside 
• 273397-26-5 methyl 2,3-di-O-benzoyl-6-O-(4-methoxybenzyl)-α-D-galactopyranoside 
• 294639-18-2 methyl 4-amino-2,3-di-O-benzoyl-4-deoxy-6-O-(4-methoxybenzyl)-α-D-glucopyranoside 
• 294639-16-0 methyl 4-azido-2,3-di-O-benzoyl-4-deoxy-6-O-(4-methoxybenzyl)-α-D-glucopyranoside 
• 294639-14-8 methyl 2,3-di-O-benzoyl-4-O-mesyl-6-O-(4-methoxybenzyl)-α-D-galactopyranoside 
• 131613-82-6 (2S,4aR,6S,7R,8S,8aS)-7,8-bis(benzyloxy)-6-methoxy-2-(4-methoxyphenyl)hexahydropyrano[3,2-d][1,3]dioxine 
• 94827-31-3 methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-α-D-galactopyranoside 
• 540776-09-8 (1R,2S,3S,4S,5R)-4-(hydroxymethyl)-6-azabicyclo[3.1.0]hexane-2,3-diol 

Relevant academic research and scientific papers

Rational Design of Mechanism-Based Inhibitors and Activity-Based Probes for the Identification of Retaining α-l-Arabinofuranosidases

Identifying and characterizing the enzymes responsible for an observed activity within a complex eukaryotic catabolic system remains one of the most significant challenges in the study of biomass-degrading systems. The debranching of both complex hemicell

Mild One-Step Synthesis of 4,6-Benzylideneglycopyranosides from Aromatic Aldehydes and Gelation Abilities of the Glucose Derivatives

We report herein an efficient one-step synthesis of 4,6-benzylidene glycoside derivatives from aromatic aldehydes bearing electron-donating or -withdrawing groups as well as polymerisable monomer groups. Glucose, mannose and galactose derivatives could also be used successfully. Several of the glucose derivatives thus obtained acted as gelators for various solvents, including water. 4-(n-Butoxybenzylidene)glucose derivative 3a produced both a clear squalane gel and a hydrogel at 0.1 wt.-%. Furthermore, 3-(n-butoxybenzylidene)glucose derivative 3i produced a clear organogel and an opaque hydrogel. The critical gelation concentration (CGC) of 3i in squalane was determined to be 0.02 wt.-%, which is one of the lowest CGC values reported so far. The organogels, hydrogels and aqueous solution gels produced from 3a and 3d exhibited thixotropy. The strength and thixotropy of the organo- and hydrogel produced from 3a were estimated by a rheometer. The gel morphologies were observed by field-emission and wet-scanning electron microscopy, and the self-assembly modes were analysed by XRD. We have concluded that super-gelators can be created by this method. An efficient one-step synthesis of 4,6-benzylidene glycosides from aromatic aldehydes under mild conditions has been achieved. Some of the glucose derivatives synthesised by this method produced clear organo- and hydrogels with thixotropic properties. The critical gelation concentrations of the gels were below 0.1 wt.-%.

Organocatalysis for the acid-free O-arylidenation of carbohydrates

Methyl glycopyranosides of glucose, galactose, and mannose, their 2,3-di-O-benzyl-protected derivatives, as well as the unprotected sugars react with p-methoxybenzaldehyde dimethyl acetal (3) and with benzaldehyde dimethyl acetal (7) as reagents in the presence of thiourea 1 or squaramide 2 as the organocatalyst to afford regioselectively 4,6-O-arylidenated derivatives 5 and 8. With an excess amount of 3 or 7, diarylidenated derivatives are also obtained. In situ formation of acetals of type 3 and 7 from corresponding aldehydes 10 and 13 in the presence of an orthoester and organocatalyst 1 or 2 can be used to generate 5 and 8 directly from the aldehydes. Some substrates also lead to mixed orthoesters with this procedure. The reaction courses are discussed. A squaramide catalyzes the 4,6-O-arylidenation of glucose, mannose, and galactose with the use of arenecarbaldehyde dimethyl acetals or arenecarbaldehydes and orthoesters as the reagents. Glycoside derivatives also undergo this reaction. Copyright

Environmentally benign preparation of benzylidene acetal of carbohydrate derivatives in PEG 600

An environmentally benign preparation of benzylidene acetal of carbohydrate derivatives catalyzed by HClO4-SiO2 in PEG 600 as solvent has been developed. Yields were excellent in every case. Copyright Taylor & Francis Group, LLC.

Stripping off water at ambient temperature: Direct atom-efficient acetal formation between aldehydes and diols catalyzed by water-tolerant and recoverable vanadyl triflate

(Chemical Equation Presented) Aromatic aldehydes can be readily protected as acetals with 1,2- and 1,3-diols by using vanadyl triflate as a catalyst in CH3CN at ambient temperature. Carbohydrate-based 1,2- and 1,3-diols can similarly be protected in good to excellent yields. The catalyst can be readily recovered from the aqueous layer. In combination with vanadyl triflate-catalyzed sequential regioselective, reductive acetal opening and chemoselective acylations, the title method allows for differential functionalization of all four hydroxyl units in a given glucopyranoside.

Asymmetric hydrogenation - Influence of the structure of carbohydrate derived catalysts on the relative enantioselectivity Q(H/Me) regarding acid and ester substrates and its inversion - Selectivity increase in water by amphiphiles

4,6-O-Benzylidene protected 2,3-bis(O-diphenylphosphino)-D-glycopyranoside rhodium(I) chelate precatalysts 1-4 e,f showed for the hydrogenation of methyl (Z)2-N-acylamidoacrylates 6-8 a stepwise decrease of the enantioselectivity with increasing number of axially oriented hexopyranoside substituents. The decrease is even stronger for the analogous substrate acids 6h-8h resulting in an unusual low relative enantioselectivity Q = q(H)/q(Me) of 0.3 for the precatalysts 4e and 4f. Deprotected, 4,6-OH-group bearing catalysts 1-4 g,h generally show smaller differences of %ee in methanol or benzene, however, not in water. Under addition of amphiphiles a in comparison with blanks b the relative enantioselectivity Q = q(a)/q(b) clearly increases for both groups of catalysts in most cases to Q-values between 3 up to 8 - independent of a neutral or ionic nature of the amphiphile.