74808-10-9

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL TRICHLOROACETIMIDATE is used as a synthetic reagent for the preparation of natural glycosides, such as Isosyringinoside and glucopyranosyl-glucopyranosyl-hydroxy phenylethanol I. These glycosides have potential applications in the development of pharmaceuticals, as they possess various biological activities and therapeutic properties.
Used in Organic Synthesis:
In the field of organic synthesis, 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL TRICHLOROACETIMIDATE is employed as a versatile building block for the construction of complex carbohydrate structures. Its ability to form stable glycosidic bonds makes it a valuable tool for the synthesis of oligosaccharides, polysaccharides, and other carbohydrate-containing compounds with potential applications in various industries, such as pharmaceuticals, cosmetics, and food.

Upstream product

• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 545-06-2 trichloroacetonitrile 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 604-68-2 α-D-glucopyranose peracetylate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 3947-62-4 2,3,4,6-tetraacetylglucose 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 70191-05-8 2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 4163-60-4 β-D-galactose peracetate 
• 25878-60-8 D-galactose pentaacetate 
• 2280-44-6 D-Glucose 

Downstream Products

• 10343-15-4 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester 
• 10343-13-2 benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 13035-51-3 tert-butyl-(tetra-O-acetyl-β-D-glucopyranoside) 
• 53691-39-7 benzyl 3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 31281-76-2 O-benzyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 909100-00-1 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 909253-95-8 4-O-(2,3,4-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 909100-32-9 2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-6-O-β-D-glucopyranosyl-1,5-imino-D-glucitol 
• 1186009-42-6 C₄₈H₅₄O₁₆ 
• 1253227-44-9 4'-acetoxy-6,8-di-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5,7-dihydroxyflavan 
• 1253227-80-3 4'-acetoxy-6-C-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-8-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5,7-dihydroxyflavan 
• 1253227-84-7 4'-acetoxy-6-C-(2,3,4-tri-O-acetyl-α-D-arabinopyranosyl)-8-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5,7-dihydroxyflavan 
• 67909-25-5 4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 18997-57-4 4-methylumbelliferyl β-D-glucopyranoside 

Relevant academic research and scientific papers

PROCESS OF SYNTHESIS OF β-6'SULFOQUINOVOSYL DIACYLGLYCEROLS

The present invention relates to a synthesis process of β-6-sulfoquinovosyl-diacylglycerols. In particular, said process is for the synthesis of the compounds 1,2-O-distearoyl-3-O-(β- sulfoquinovosyl)-R/S-glycerol, 1,2-O-distearoyl-3-O-(β-sulfoquinovosyl)-R-glycerol or 1,2- O-distearoyl-3-O-(β-sulfoquinovosyl)-S-glycerol, named respectively Sulfavant A, Sulfavant R and Sulfavant S.

Synthesis of malformin-A1, C, a glycan, and an aglycon analog: Potential scaffolds for targeted cancer therapy

Improvement in therapeutic efficacy while reducing chemotherapeutic side effects remains a vital objective in synthetic design for cancer treatment. In keeping with the ethos of therapeutic development and inspired by the Warburg effect for augmenting biological activities of the malformin family of cyclic-peptide natural products, specifically anti-tumor activity, a β-glucoside of malformin C has been designed and synthesized utilizing precise glycosylation and solution phase peptide synthesis. We optimized several glycosylation procedures utilizing different donors and acceptors. The overarching goal of this study was to ensure a targeted delivery of a glyco-malformin C analog through the coupling of D-glucose moiety; selective transport via glucose transporters (GLUTs) into tumor cells, followed by hydrolysis in the tumor microenvironment releasing the active malformin C a glycon analog. Furthermore, total synthesis of malformin C was carried out with overall improved strategies avoiding unwanted side reactions thus increasing easier purification. We also report on an improved solid phase peptide synthesis protocol for malformin A1.

Glucose-containing nitrogen-containing aromatic ring derivative and application thereof

The invention belongs to the technical field of medicines, and relates to a glucose-containing nitrogen-containing aromatic ring derivative and application thereof, and a pharmaceutical composition containing the compound. The invention also relates to a

Self-Promoted Glycosylation for the Synthesis of β-N-Glycosyl Sulfonyl Amides

N-Glycosyl N-sulfonyl amides have been synthesized by a self-promoted glycosylation, i. e. without any catalysts, promotors or additives. When the reactions were carried out at lower temperatures a mixture of N- and O-glycosides were observed, where the latter rearranged to give the β-N-glycosides at elevated temperatures. By this method sulfonylated asparagine derivatives can be selectively β-glycosylated in high yields by trichloroacetimidate glycosyl donors of different reactivity including protected glucosamine derivatives. The chemoselectivity in the glycosylations as well as the rearrangements from O-glycosides to β-N-glycosides gives information of the glycosylation mechanism. This method gives access to glycosyl sulfonyl amides under mild conditions.

First total syntheses of two natural glycosides

Isosyringinoside (1) and 3-(O-β-D-glucopyranosyl)-α-(O-β-D-glucopyranosyl)-4-hydroxy phenylethanol (2), the natural bioactive compounds contained unique structures, were first totally synthesized using easily available materials in short convenient routes with overall yields of 20.2% and 27.0%, respectively. An efficient total synthesis of 1 was developed in six steps, which contained two key steps of highly regioselective glycosylation without any selective protection steps. The seven-step synthesis of 2 involved two steps of regioselective glycosylations using BF3–O(C2H5)2 and TMSOTf as catalysts, respectively.

Total synthesis of three natural phenethyl glycosides

Phenethyl glycosides having phenolic or methoxy functions at benzene rings are substances widely occurring in nature. This kind of compounds has been shown to have anti-oxidant, anti-inflammatory, and anticancer activities. However, some of them are not naturally abundant, thus the synthesis of such molecules is desirable. In this paper, natural phenethyl glycosides 3 and 4 were first totally synthesized from easily available materials with overall yields of 50.5% and 40.1%, respectively. And a new synthetic route to obtain natural phenethyl glycoside 2 in 46.2% yield was also described.

An alternative approach for the synthesis of sulfoquinovosyldiacylglycerol

Sulfoquinovosyldiacylglycerol (SQDG) is a glycolipid ubiquitously found in photosyn-thetically active organisms. It has attracted much attention in recent years due to its biological ac-tivities. Similarly, the increasing demand for vegan and functional foods has led to a growing interest in micronutrients such as sulfolipids and their physiological influence on human health. To study this influence, reference materials are needed for developing new analytical methods and providing enough material for model studies on the biological activity. However, the availability of these materials is limited by the difficulty to isolate and purify sulfolipids from natural sources and the unavailability of chemical standards on the market. Consequently, an alternative synthetic route for the comprehensive preparation of sulfolipids was established. Here, the synthesis of a sulfolipid with two identical saturated fatty acids is described exemplarily. The method opens possibilities for the preparation of a diverse range of interesting derivatives with different saturated and unsatu-rated fatty acids.

3'-KETOGLYCOSIDE COMPOUND FOR THE SLOW RELEASE OF A VOLATILE ALCOHOL

The present invention relates to a 3'-ketoglycoside compound defined by formula (I) and its use for controlled release of alcohols, in particular alcohols showing an insect repellent effect. It relates also to a process for preparing the 3'-ketoglycoside compound of formula (I). It further relates to a composition comprising a 3'- ketoglycoside compound of formula (I). It relates also to the use of a 3'-ketoglycoside compound of formula (I) for the controlled release of alcohols. It related also to a method of use of such composition.

Revealing Functional Significance of Interleukin-2 Glycoproteoforms Enabled by Expressed Serine Ligation

Naturally occurring interleukin-2 (IL-2) is a pleiotropic glycoprotein that regulates immune responses by controlling the differentiation and homeostasis of T cells. Non-glycosylated IL-2 has been used in clinical settings for three decades. However, the function of the O-glycan of native IL-2 remains elusive. Herein, to stress this issue, we report a highly efficient semi-synthesis of homogeneous glycosylated IL-2 with various glycoproteoforms on a multi-milligram scale. The glycopeptide fragment was prepared by chemical synthesis and then merged with recombinant fragment via a serine ligation to generate the desired glycoprotein in a single operation. Biological evaluation of the homogenous glycoprotein library reveals that the activity of IL-2 in activating individual T cell subset is glycan dependent, thus highlighting the possibility of further improving current clinical medicine.