183875-22-1

Upstream product

• 171032-74-9 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose 
• 108-98-5 thiophenol 
• 90-76-6 2-deoxy-2-amino glucose 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 4551-15-9 phenylthiotrimethylsilane 

Downstream Products

• 3947-65-7 neomycin A 
• 632330-84-8 phenyl 2,6-diazido-2,6-dideoxy-1-thio-α/β-D-glucopyranoside 
• 632330-83-7 Toluene-4-sulfonic acid (2R,3S,4R,5R)-5-azido-3,4-dihydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester 
• 549501-23-7 (3R,4R,5R,6R)-3-Azido-6-azidomethyl-4,5-bis-benzyloxy-2-phenylsulfanyl-tetrahydro-pyran 
• 549501-35-1 (1S,2R,3R,4S,6R)-4,6-Diamino-3-((2R,3R,4R,5R,6R)-3-amino-6-aminomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol 
• 549501-27-1 3′,4′-di-O-benzyl-1,3,2′,6′-tetraazidoneamine 
• 549501-26-0 5,6-di-O-acetyl-3',4'-di-O-benzyl-1,3,2',3'-tetraazidoneamine 
• 1021183-18-5 C₂₆H₂₆IN₃O₇S 

Relevant academic research and scientific papers

GLYCOSYLATED ANTITUMOR ETHER LIPIDS AS NOVEL CANCER STEM CELL CYTOTOXIC AGENTS

Glycosylated antitumor ether lipids (GAELs) are effective cytotoxic agents against cancer stem cells. Furthermore, combining GAELs which kill cells by a caspase-independent pathway with agents that kill cells by apoptosis will lead to elimination of the differentiated tumor cells and the undifferentiated cancer stem cells leading to an elimination of the tumor and preventing recurrence.

A METHOD FOR OBTAINING CRYSTALLINE LACTO-N-TETRAOSE AND LACTO-N-NEOTETRAOSE PRECURSORS AND MIXTURES THEREOF

A mixture of, preferably a mixture consisting essentially of, an lacto-N-tetraose (LNT) precursor (1) and an lacto-N-neotetraose (LNnT) precursor (2), (formula 1, 2), where R is a group removable by hydrogenolysis and R3 is either a group remov

SOMATOSTATIN MIMETICS

Somatostatin is a tetradecapeptide that regulates, through binding to its receptors (SSTRs), a number of processes including the release of growth hormone and other pituitary hormones. Disclosed herein are a number of somatostatin mimetics that exhibit potential utility as therapeutic agents. Formula (I)

Synthesis of a benzomacrolactone-based somatostatin mimetic

The benzomacrolactone is a framework found in numerous natural products. The synthesis of an orthogonally functionalized benzomacrolactone from d-glucosamine and a salicylic acid derivative is described. This macrolactone was used for the synthesis of a somatostatin mimetic that has submicromolar affinity for the human somatostatin receptor 4 (hSSTR4).

Synthesis of aminoglycoside derivatives on a Cbz-type heavy fluorous tag

Four aminoglycoside derivatives containing a 2,6-diamino-2,6-dideoxy-d-glucopyranose disaccharide structure were successfully prepared by using a Cbz-type heavy fluorous tag in a fluorous synthesis. A Cbz-type heavy fluorous tag was prepared using the hex

Synthesis of (+),(-)-neamine and their positional isomers as potential antibiotics

The syntheses of (+)-neamine 1, (-)-neamine ent-1 and their positional isomers 2, 3, ent-2 and ent-3 are reported as potential new scaffolds for novel aminoglycoside antibiotics. These isomers exhibit similar inhibitory activities, as shown using an in vitro translation assay. A simple model is proposed to explain this lack of stereospecific binding to the ribosomal RNA.

AMINOGLYCOSIDE ANTIBIOTICS AND METHODS OF USING SAME

The present invention relates to aminoglycoside compounds having antibiotic activity. Moreover, the present invention relates to L-aminoglycoside compounds and diastereomers thereof which posses antibiotic activity and are not susceptible to development of resistant bacterial strains. The present invention also relates to methods of treatment and pharmaceutical compositions that utilize or comprise one or more of aminoglycoside compounds provided by the invention.

Attempted synthesis of type-A inositolphosphoglycan mediators - Synthesis of a pseudohexasaccharide precursor

A block synthesis approach to the inositol-containing pseudohexasaccharide 1 is presented. The myo-inositol building block 6 has been prepared using a key regioselective acylation through a boron-tin exchange reaction and the 2-azido-2-deoxy glycosyl donors 15 and 17 have been synthesized from D-glucosamine using a diazo transfer reaction. The anomeric position of the mono- and disaccharide building blocks has been temporarily protected as phenyl thioglycoside and this function was then converted into the different leaving groups to perform the glycosylation reactions. Both trichloroacetimidates and fluorides have been used as glycosyl donors for the construction of the different glycosidic linkages. The protected pseudohexasaccharides 44, 48-50, which are precursors of pseudohexasaccharide 1, have been efficiently prepared and fully characterized. Pseudohexasaccharide 1 contains the fundamental structural features which have been proposed for type A inositolphosphoglycans, which may be involved in the insulin-signaling process.

Generalizing glycosylation: Synthesis of the blood group antigens Lea, Leb, and Le(x) using a standard set of reaction conditions

Because there are no general reaction conditions for any glycosylation method, biologically interesting oligosaccharides can only be made in a small number of laboratories in the world. To make carbohydrate synthesis accessible to nonspecialists, it is critical to have glycosylation methods that will work in a wide range of cases under a single set of conditions. The Lewis blood group antigens have attracted the attention of numerous synthetic carbohydrate groups because of their structural complexity. Although they have been synthesized many times, they have never been made using a single glycosylation method under one set of reaction conditions. In this paper, we show that the sulfoxide glycosylation method can be used to form all of the glycosidic linkages in the Lewis blood group antigens Lea (1), Leb (2), and Le(x) (3) stereoselectively under a uniform set of reaction conditions. This work highlights the flexibility of the sulfoxide method and demonstrates its utility for constructing families of related oligosaccharides.