19488-49-4

Upstream product

• 53685-11-3 (2R,3R,4S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol 
• 100-44-7 benzyl chloride 
• 88819-23-2 Methyl 3,6-di-O-benzyl-α-D-galactopyranoside 
• 620-05-3 iodomethylbenzene 
• 100-39-0 benzyl bromide 
• 3396-99-4 methyl α-D-galactopyranoside 
• 98807-61-5 1-O-methyl-2,3,6-tri-O-benzyl-4-keto-α-D-glucopyranoside 
• 145933-55-7 methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-α-D-lyxo-hexopyranosyl-2-ulose 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-α-D-galactopyranoside 
• 53008-63-2 methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 
• 7177-79-9 (2R,4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 29388-46-3 methyl 2,3-di-O-benzyl-α-D-galactopyranoside 

Downstream Products

• 24679-79-6 2,3,6-tri-O-benzyl-D-glucopyranoside 
• 112260-57-8 methyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 70255-93-5 Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 
• 96323-30-7 methyl 4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 95217-08-6 1,4-anhydro-2,3,6-tri-O-benzyl-β-D-galactopyranose 
• 71454-40-5 Methyl 2,3,6-tri-O-benzyl-4-O-(methanesulfonyl)-α-D-galactopyranoside 
• 55697-55-7 methyl 2,3,6-tri-O-benzyl-4-O-methyl-α-D-galactopyranoside 
• 348631-15-2 methyl 4‐O‐(2,3‐di‐O‐benzyl‐4,6‐O‐benzylidene‐α‐D‐glucopyranosyl)‐2,3,6‐tri‐O‐benzyl‐α‐D-galactopyranoside 
• 172297-88-0 methyl 2,3,6-tri-O-benzyl-4-deoxy-β-L-threo-hex-4-enopyranoside 
• 432038-84-1 methyl 2,3,6-tri-O-benzyl-4-O-(1H-imidazol-1-ylsulfonyl)-α-D-galactopyranoside 
• 68622-25-3 Methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside 
• 936132-22-8 methyl 2,3,6-tri-O-benzyl-4-O-[(N-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)carbamoyl]-α-D-galactopyranoside 

Relevant academic research and scientific papers

Methyl 4-O-β-L-galactopyranosyl-β-D-glucopyranoside (methyl β-L-lactoside)

Methyl β-l-lactoside, C13H24O11, (II), is described by glycosidic torsion angles φ (O5Gal - C1Gal - O4Glc - C4Glc) and ψ (C1 Gal - O1Gal - C4Glc - C5Glc) of 93.89 (13) and -127.43 (13)°, respectively, where the ring atom numbering conforms to the convention in which C1 is the anomeric C atom and C6 is the exocyclic hydroxymethyl (CH2OH) C atom in both residues (Gal is galactose and Glc is glucose). Substitution of l-Gal for d-Gal in the biologically relevant disaccharide, methyl β-lactoside [Stenutz, Shang & Serianni (1999). Acta Cryst. C55, 1719-1721], (I), significantly alters the glycosidic linkage interface. In the crystal structure of (I), one inter-residue (intramolecular) hydrogen bond is observed between atoms H3O Glc and O5Gal. In contrast, in the crystal structure of (II), inter-residue hydrogen bonds are observed between atoms H6OGlc and O5Gal, H6OGlc and O6Gal, and H3O Glc and O2Gal, with H6OGlc serving as a donor with two intramolecular acceptors.

A Chiral Copper Catalyzed Site-Selective O-Alkylation of Carbohydrates

Highly regioselective alkylation of sugar hydroxyl groups has always been an important challenge in carbohydrate chemistry, especially for the selective alkylation of trans diols, there is no direct and efficient catalytic method so far. A chiral copper c

Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions

The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.

Regio/site-selective alkylation of substrates containing a: Cis -, 1,2- or 1,3-diol with ferric chloride and dipivaloylmethane as the catalytic system

In this study, we reported the regio/site-selective alkylation of substrates containing a cis-, 1,2- or 1,3-diol with FeCl3 as a key catalyst. A catalytic system consisting of FeCl3 (0.01-0.1 equiv.) and dipivaloylmethane (FeCl3/dipivaloylmethane = 1/2) was used to catalyze the alkylation in the presence of a base. The produced selectivities and isolated yields were similar to those obtained by methods using the same amount of FeL3 (L = acylacetone ligand) as the catalyst in most cases. The previously reported FeL3 catalysts for alkylation are not commercially available and have to be synthesized prior to use. In contrast, FeCl3 and dipivaloylmethane (Hdipm) are very common and inexpensive nontoxic reagents in the lab, thereby making the method much greener and easier to handle. Mechanism studies confirmed for the first time that FeCl3 initially reacts with two equivalents of Hdipm to form [Fe(dipm)3] in the presence of a base in acetonitrile, followed by the formation of a five or six-membered ring intermediate between [Fe(dipm)3] and two hydroxyl groups of the substrate. A subsequent reaction between the cyclic intermediate and the alkylating agent results in selective alkylation of the substrate.

Organotin-catalyzed regioselective benzylation of carbohydrate trans-diols

A convenient approach to regioselective benzylation of carbohydrate trans-diols was developed, where 0.1 equiv. of Bu2SnCl2 and 0.1 equiv. of TBABr were used as the catalysts and 2.0 equiv. of BnCl was used as the benzylation reagent. In most cases, similar or better benzylation regioselectivities and isolated yields were obtained by using catalytic amounts of Bu2SnCl2, rather than stoichiometric amounts of organotin reagents required.

An Iron(III) Catalyst with Unusually Broad Substrate Scope in Regioselective Alkylation of Diols and Polyols

In this study, [Fe(dibm)3] (dibm=diisobutyrylmethane) is shown to have unusually broad scope as a catalyst for the selective monoalkylation of a diverse set of 1,2- and 1,3-diol-containing structures. The mechanism is proposed to proceed via a cyclic dioxolane-type intermediate, formed between the iron(III) species and two adjacent hydroxyl groups. This approach represents the first transition-metal catalysts that are able to replace stoichiometric amounts of organotin reagents in regioselective alkylation. The reactions generally lead to very high regioselectivities and high yields, on par with, or better than, previous methods used for regioselective alkylation.

HClO4-silica-catalysed regioselective opening of benzylidene acetals and its application towards regioselective HO-4 glycosylation of benzylidene acetals in one-pot

Here we report a high-yielding method for the regioselective reductive ring opening of 4,6-O-benzylidene acetals of hexapyranosides using inexpensive and robust HClO4-SiO2 as the acidic catalyst and triethylsilane as the hydride dono

Mannose-binding geometry of pradimicin A

Pradimicins (PRMs) and benanomicins are the only family of non-peptidic natural products with lectin-like properties, that is, they recognize D-mannopyranoside (Man) in the presence of Ca2+ ions. Coupled with their unique Man binding ability, t

Control of the ambident reactivity of the nitrite ion

In previous studies, it was reported that a neighbouring equatorial ester group is essential for a good yield of nitrite-mediated triflate inversion, whereas with neighbouring benzyl ether groups or axial ester groups, mixtures are generally produced. In

TMDS as a dual-purpose reductant in the regioselective ring cleavage of hexopyranosyl acetals to ethers

1,1,3,3-Tetramethyldisiloxane (TMDS) has been developed as an excellent dual-purpose reductant for the highly regioselective ring cleavage of various hexopyranosyl 4,6-O-acetals with Cu(OTf)2 or AlCl3 to afford the corresponding prim