131089-34-4

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 67-56-1 methanol 
• 87316-22-1 (2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol 

Downstream Products

• 131089-35-5 methyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside 
• 186540-03-4 tert-Butyl-diphenyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane 
• 178885-10-4 methyl 3-O-benzoyl-6-O-[(tert-butyl)diphenylsilyl]-α-D-mannopyranoside 
• 858106-56-6 phenyl 2,3,4-tri-O-methyl-6-O-[methyl-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranos-3-yloxy)-2-carbonylbenzoyl]-1-thio-α-D-mannopyranoside 
• 858106-57-7 phenyl 2,3,4-tri-O-acethyl-6-O-[methyl-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranos-3-yloxy)-2-carbonylbenzoyl]-1-thio-α-D-mannopyranoside 
• 872352-29-9 Acetic acid (2R,3R,4S,6S)-4-allyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-oxo-tetrahydro-pyran-3-yl ester 
• 872352-58-4 4-O-acetyl-3-O-allyl-6-tert-butyldiphenylsiloxy-β-D-methylmannopyranoside 
• 172688-33-4 (5R,6S,7R)-5,6,7trihydro-5-(1R-1,2-dihydroxyethyl)-6,7-O-isopropylidenepyrrolo<1,2-d>tetrazole-6,7-diol 
• 172688-29-8 methyl 4-azido-4-deoxy-6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside 
• 172688-40-3 (5R,6S,7R)-5,6,7-trihydro-5-(1R-1-hydroxyethyl)-6,7-O-isopropylidenepyrrolo<1,2-d>tetrazole-6,7-diol 
• 172688-48-1 methyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-talopyranoside 
• 1616283-56-7 methyl-6-O-tert-butyldiphenylsilyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranoside 

Relevant academic research and scientific papers

Palladium-Catalyzed ortho-C-H Glycosylation/ ipso-Alkenylation of Aryl Iodides

This report describes the first example of palladium-catalyzed ortho-C-H glycosylation/ipso-alkenylation of aryl iodides, and the easily accessible glycosyl chlorides are used as a glycosylation reagent. The reaction is compatible with the functional groups of the substrates, and a series of C-aryl glycosides have been synthesized in good to excellent yield and with excellent diastereoselectivity. It is found that a cheap 5-norbornene-2-carbonitrile as a transient mediator can effectively promote this reaction. In addition, ipso-arylation and cyanation were also realized by the strategy.

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

One-pot synthesis of orthogonally protected sugars through sequential base-promoted/acid-catalyzed steps: A solvent-free approach with self-generation of a catalytic species

A varied set of solvent-free, one-pot synthetic sequences were developed to carry out the orthogonal protection of saccharide polyols. These sequences are composed of an initial regioselective benzylation, silylation or iodination (under mildly basic cond

Orthogonal protection of saccharide polyols through solvent-free one-pot sequences based on regioselective silylations

tert-Butyldimethylsilyl (TBDMS) and tert-butyldiphenylsilyl (TBDPS) are alcohol protecting groups widely employed in organic synthesis in view of their compatibility with a wide range of conditions. Their regioselective installation on polyols generally r

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

Tandem epoxidation-alcoholysis or epoxidation-hydrolysis of glycals catalyzed by titanium(IV) isopropoxide or Venturello's phosphotungstate complex

Venturello's phosphotungstate complex and titanium(IV) isopropoxide [Ti(O-i-Pr)4] were successfully used as catalysts for the epoxidation-alcoholysis of glycals using hydrogen peroxide [H2O 2]. Reaction substrates included a range of variously protected glycals and different alcohols were used as solvents. Ti(O-i-Pr)4 was only effective in methanol as solvent, but gave methyl glycosides in high yields and high selectivities. The Venturello complex proved to be a very versatile and efficient catalyst. Apart from epoxidation-alcoholysis in alcoholic solvents it also showed activity in biphasic conditions to allow for glycosylation of long-chain alcohols and was very effective in the stereoselective dihydroxylation of benzylated glucal.

Indium triflate catalyzed peracetylation of carbohydrates

Peracetylation is a very common protection strategy that is widely implemented in carbohydrate synthesis. Here, a method for the peracetylation of carbohydrates using catalytic In(OTf)3 in neat acetic anhydride is reported. In(OTf)3 has low toxicity and is mild and water tolerant, and the reactions are high yielding and efficient. Details regarding the scope and mechanism of the reaction are briefly discussed.

Chemoenzymatic synthesis of GDP-azidodeoxymannoses: Non-radioactive probes for mannosyltransferase activity

GDP-2-, 3-, 4- or 6-azidomannoses can be successfully prepared from the corresponding azidomannose-1-phosphates and GTP using the enzyme GDP-Mannosepyrophosphorylase (GDP-ManPP) from Salmonella enterica and may serve as useful probes for mannosyltransferase activity. The Royal Society of Chemistry.

Application of the anomeric samarium route for the convergent synthesis of the C-linked trisaccharide α-D-Man-(1→3)-[α-D-Man-(1→6)]-D-Man and the disaccharides α-D-Man-(1→3)-D-Man and α-D-Man-(1→6)-D-Man

Studies are reported on the assembly of the branched C-trisaccharide, α-D-Man-(1→3)-[α-D-Man-(1→6)]-D-Man, representing the core region of the asparagine-linked oligosaccharides. The key step in this synthesis uses a SmI2-mediated coupling of two mannosylpyridyl sulfones to a C3,C6-diformyl branched monosaccharide unit, thereby assembling all three sugar units in one reaction and with complete stereocontrol at the two anomeric carbon centers. Subsequent tin hydride-based deoxygenation followed by a deprotection step produces the target C-trimer. In contrast to many of the other C-glycosylation methods, this approach employes intact carbohydrate units as C-glycosyl donors and acceptors, which in many instances parallels the well-studied O-glycosylation reactions. The synthesis of the C-disaccharides α-D-Man-(1→3)-D-Man and α-D-Man-(1→6)-D-Man is also described, they being necessary for the following conformational studies of all three carbohydrate analogues both in solution and bound to several mannose-binding proteins.

Highly efficient and practical synthesis of 3,6-branched oligosaccharides.

[reaction: see text] A one-pot formation of the 3- and 6-OH differentially protected sugar synthon was described. A mannopyranosyl pentasaccharide and a glucopyranosyl hexasaccharide were prepared employing this new finding.