4056-12-6

Upstream product

• 97-30-3 methyl-alpha-D-glucopyranoside 
• 98-80-6 phenylboronic acid 

Downstream Products

• 41356-06-3 Methyl-<α-D-glucopyranosid>-2,3--4,6-phenylboronat 
• 122971-00-0 methyl O²,O³-dibenzoyl-O⁴,O⁶-phenylboranediyl-α-D-glucopyranoside 
• 108884-73-7 methyl O²,O³-dimethyl-O⁴,O⁶-phenylboranediyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 113544-26-6 methyl 3,4,6-tri-O-acetyl-2-O-trityl-α-D-glucopyranoside 
• 4137-35-3 methyl 2,3-di-O-benzoyl-α-D-glucopyranoside 
• 222545-13-3 methyl 2,3-di-O-(4-methoxyphenylmethyl)-α-D-glucopyranoside 
• 37180-44-2 methyl 3-O-acetyl-α-D-glucopyranoside 
• 37180-43-1 2-O-acetyl-methyl α-D-glucopyranoside 
• 29868-42-6 methyl 2,3-di-O-acetyl-α-D-glucopyranoside 
• 604-70-6 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester 
• 21056-54-2 methyl 3-O-benzoyl-α-D-glucopyranoside 
• 21056-53-1 methyl O²-benzoyl-α-D-glucoside 

Relevant academic research and scientific papers

Boronic esters as protective groups in carbohydrate chemistry: processes for acylation, silylation and alkylation of glycoside-derived boronates

Procedures for selective installation of acyl, silyl ether and para-methoxybenzyl (PMB) ether groups to glycoside substrates have been developed, employing phenylboronic esters as protected intermediates. The sequence of boronic ester formation, functiona

Highly Regioselective Monoacylation of Unprotected Glucopyranoside Using Transient Directing-Protecting Groups

The regioselective functionalization of monosaccharides is notoriously achieved using metal catalysis, lengthy synthetic strategies requiring protection/deprotection, various enzymes, or other methods that target cis-diols (and thus cannot be used with glucopyranose derivatives), In this paper, we report a new method using selected boronic acids as temporary protecting groups, and describe its application to the regioselective functionalization of methyl α-d-glucopyranoside, the most difficult monosaccharide to functionalize regioselectively. Generally, reactions of glucopyranosides may lead to a plethora of mono- and polyfunctionalized derivatives, yet our method gave the 3-O-acetylated, 2-O-benzoylated, and 2-O-pivaloylated derivatives of methyl α-d-glucopyranoside as major products. We focused on the use of recyclable and green temporary protecting groups (in a one-pot reaction) and on the modulation of the intramolecular hydrogen-bonding network using selected arylboronic acids. A complete scalable procedure leading to a single regioisomer from unprotected methyl α-d-glucopyranoside is presented.

Sequential Functionalizations of Carbohydrates Enabled by Boronic Esters as Switchable Protective/Activating Groups

Processes for site-selective, sequential functionalizations of carbohydrate derivatives are described. In these processes, a tricoordinate boronic ester initially serves as a protective group for a sugar-derived 1,2- or 1,3-diol motif, permitting functionalization of free OH groups. In a second step, addition of a Lewis base generates a tetracoordinate adduct, which serves as an activating group, enabling functionalization of one of the boron-bound oxygen atoms by a second electrophile. By combining an initial acylation, alkylation, or glycosylation step with an amine-mediated glycosylation of the boronic ester, a variety of selectively protected di- and trisaccharide derivatives can be accessed in an operationally simple fashion without purification of intermediates. This Lewis base-triggered switching of behavior from "latent" to "active" nucleophile is a unique feature of boronic esters relative to other protective groups for diol moieties in carbohydrate chemistry.

Regioselective, Tin-Free Sulfation of Unprotected Hexopyranosides by Using Phenylboronic Acid

Regioselective, tin-free sulfation of a number of unprotected glycopyranosides derived from L-fucose, L-rhamnose, D-arabinose, D-glucose, D-galactose, and D-trehalose was achieved by using phenylboronic acid for masking the hydroxy groups and a 2,2,2-trichloroethyl-protected sulfurylimidazolium salt as the sulfating reagent. The formation of phenylborate ester remarkably improved the solubility of the carbohydrates in organic solvents and indicated high reactivity and regioselectivity in the sulfation reactions. This methodology was successfully adapted to result in a one-pot procedure that did not require separation or purification of the reaction intermediates.

Seven-membered ring boronates at trans-diol moieties of carbohydrates

MS and 1H, 13C and 11B NMR results are presented revealing the formation of cyclic seven-membered boronate structures at trans-1,2-diol moieties of carbohydrates providing new opportunities for the activation, protection and analysis of glucopyranose-based oligomers and polymers such as cellulose or starch. 'Coordination-induced shifts' in 13C NMR spectra were identified for the esterification by boronic acids of carbohydrates, which can be applied for further studies.