82264-32-2

Upstream product

• 6748-91-0 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 492-62-6 alpha-D-glucopyranose 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 709-50-2 methyl beta-D-glucopyranoside 
• 100-44-7 benzyl chloride 
• 162284-50-6 methyl 2,3-di-O-acetyl-6-O-benzyl-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 67-56-1 methanol 
• 115850-12-9 p-nitrophenyl 6⁵-O-benzyl-α-maltopentaoside 

Downstream Products

• 863554-17-0 (3aR,4R,6S,7aR)-4-Benzyloxymethyl-6-methoxy-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one 
• 863554-23-8 methyl 6-O-benzyl-3,4-O-isopropylidene-α-D-allopyranoside 
• 1613160-53-4 methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-allo-hexopyranosid-4-ulose 
• 1613160-54-5 methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-allopyranoside 
• 1613160-55-6 methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-allopyranoside 
• 1613160-51-2 methyl 6-O-benzyl-3,4-O-isopropylidene-α-D-glucopyranoside 
• 1613160-52-3 methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-glucopyranoside 
• 71512-68-0 methyl 1,2,4-tri-O-acetyl-6-O-benzyl-α-D-glucopyranoside 
• 71512-67-9 methyl 1,2,4-tri-O-acetyl-6-O-benzyl-β-D-glucopyranoside 
• 245047-76-1 Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-2-benzyloxymethyl-6-methoxy-5-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-ethoxy)-tetrahydro-pyran-3-yl ester 
• 245047-73-8 methyl 3,4-di-O-acetyl-6-O-benzyl-2-O-[8-(tert-butyldimethylsilyloxy)-3,6-dioxaoctyl]-α-D-glucopyranoside 
• 245047-80-7 methyl 6-O-benzyl-2-O-(11,14-dioxo-3,6-dioxa-9-thiapentadecyl)-α-D-glucopyranoside 
• 245047-77-2 methyl 6-O-benzyl-2-O-(8-p-tolylsulfonyl-3,6-dioxaoctyl)-α-D-glucopyranoside 
• 245047-75-0 Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-2-benzyloxymethyl-5-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-6-methoxy-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

BORON CLUSTER-COUPLED COMPOUND

To provide a novel boron-containing compound which increases intratumorous accumulation and tumor retention, and is efficiently taken into a tumor cell.SOLUTION: The present invention relates to a compound represented by formula (I) in the figure or a salt thereof. [In the formula, X represents a divalent to pentavalent organic group; Y represents a linker structure; R represents a monovalent group comprising boron clusters; and n represents 2, 3, 4 or 5.SELECTED DRAWING: None

Both d - And l -Glucose Polyphosphates Mimic d - myo-Inositol 1,4,5-Trisphosphate: New Synthetic Agonists and Partial Agonists at the Ins(1,4,5)P3Receptor

Chiral sugar derivatives are potential cyclitol surrogates of the Ca2+-mobilizing intracellular messenger d-myo-inositol 1,4,5-trisphosphate [Ins(1,4,5)P3]. Six novel polyphosphorylated analogues derived from both d- and l-glucose were synthesized. Binding to Ins(1,4,5)P3 receptors [Ins(1,4,5)P3R] and the ability to release Ca2+ from intracellular stores via type 1 Ins(1,4,5)P3Rs were investigated. β-d-Glucopyranosyl 1,3,4-tris-phosphate, with similar phosphate regiochemistry and stereochemistry to Ins(1,4,5)P3, and α-d-glucopyranosyl 1,3,4-tris-phosphate are full agonists, being equipotent and 23-fold less potent than Ins(1,4,5)P3, respectively, in Ca2+-release assays and similar to Ins(1,4,5)P3 and 15-fold weaker in binding assays. They can be viewed as truncated analogues of adenophostin A and refine understanding of structure-activity relationships for this Ins(1,4,5)P3R agonist. l-Glucose-derived ligands, methyl α-l-glucopyranoside 2,3,6-trisphosphate and methyl α-l-glucopyranoside 2,4,6-trisphosphate, are also active, while their corresponding d-enantiomers, methyl α-d-glucopyranoside 2,3,6-trisphosphate and methyl α-d-glucopyranoside 2,4,6-trisphosphate, are inactive. Interestingly, both l-glucose-derived ligands are partial agonists: they are among the least efficacious agonists of Ins(1,4,5)P3R yet identified, providing new leads for antagonist development.

Dual-participation protecting group solves the anomeric stereocontrol problems in glycosylation reactions

The 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) group permits, via robust neighboring group participation (NGP) or long distance participation (LDP) effects, the stereocontrolled 1,2-trans, 1,2-cis, as well as β-2,6-dideoxy glycosidic bond generation, while suppressing the undesired orthoester byproduct formation. The robust stereocontrol capability of the DMNPA is due to the dual-participation effect from both the ester functionality and the nitro group, verified by control reactions and DFT calculations and further corroborated by X-ray spectroscopy.

Tin-mediated regioselective benzylation and allylation of polyols: Applicability of a catalytic approach under solvent-free conditions

The first catalytic version of the stannylene-mediated benzylation and allylation of polyols is reported. The methodology is based on a simple solvent-free protocol that significantly advances, in terms of both experimental ease and synthetic scope, the a

Regioselectivity of tin-mediated benzylation of glycoside

Regioselectivity of methyl α-D-glucopyranoside benzylation using dibutyltin dimethoxide (DBDM) as stannylating agent was probed, general factors affecting regioselectivity have been examined. The results show the O-2 position of glucoside has advantage of

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

Selective protection of hydroxy group at C6 position of glucose derivatives

6-O-Benzyl derivatives and 6-O-toluoyl derivatives, 2a-f and 3a-f, were prepared in high yields from glucose derivatives 1a-f through multi-level anion formation using an excess of sodium hydride (4 eq.).

Tandem catalysis for a one-pot regioselective protection of carbohydrates: The example of glucose

(Chemical Equation Presented) Fine-tuning the conditions for a tandem reaction using a single catalyst in a single reaction vessel leads to carbohydrate building blocks displaying different patterns of protecting groups (see picture). This process greatly simplifies the access to oligomers, as illustrated by the rapid assembly of a trisaccharide.

REGIOSELECTIVE FORMATION OF DI-O-BENZYL-SUBSTITUTED HEXOPYRANOSIDES VIA STANNYLENE ACETAL INTERMEDIATES

The reactions of dibutylstannylene acetals derived from several methyl hexopyranosides with benzyl bromide have been investigated.These reactions occur readily in benzyl bromide at 85 deg C.At reaction times of one to two days, the major products are di-O-benzyl derivatives.In several cases, single di-O-benzyl derivatives are the predominant products: methyl α-D-glucopyranoside and methyl β-D-galactopyranoside gave the 2,6- and 3,6-di-O-benzyl ethers in 82 and 70percent yields, respectively.The species present in these reactions and the reaction pathway are discussed.