18546-25-3

Upstream product

• 58871-04-8 6-O-p-toluenesulfonyl-D-arabino-hex-1-enitol 
• 108-24-7 acetic anhydride 
• 82295-98-5 3,4-di-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol 
• 98-59-9 p-toluenesulfonyl chloride 
• 55500-08-8 2,3,4-tri-O-acetyl-6-O-(p-toluenesulfonyl)-α-D-glucopyranosyl bromide 
• 13046-90-7 2,3,4-tri-O-acetyl-6-O-(p-toluenesulfonyl)-α-D-mannopyranosyl bromide 
• 13265-84-4 D-glucal 
• 2873-29-2 D-glucal triacetate 
• 83-87-4 D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 59202-80-1 Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-6-bromo-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 103725-99-1 Acetic acid (2R,3R,4S,5R)-3-acetoxy-6-bromo-5-(toluene-4-sulfonyloxy)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester 
• 50-99-7 D-glucose 

Downstream Products

• 84679-45-8 (+)-(5S,6R)-5-Acetoxy-5,6-dihydro-6-(tosyloxymethyl)-2H-pyran-2-one 
• 144850-03-3 3,4-Di-O-acetyl-2-deoxy-2-iodo-6-O-p-toluenesulphonyl-α-D-mannopyranose 
• 144850-02-2 1,3,4-Tri-O-acetyl-2-deoxy-2-iodo-6-O-p-toluenesulphonyl-α-D-mannopyranose 
• 590384-08-0 acetyl 2-deoxy-3,4-di-O-acetyl-6-O-tosyl-α/β-D-glucopyranose 
• 148553-47-3 1,5-anhydro-3-O-tert-butyldiphenylsilyl-2,6-dideoxy-D-arabino-hex-1-enitol 
• 194592-67-1 Acetic acid (2R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran-3-yl ester 
• 381727-54-4 Benzoic acid (2R,3R,4R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester 
• 153596-70-4 methyl 3-O-benzyl-4-O-(3-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside 
• 117399-36-7 3,4-di-O-benzyl-2,6-dideoxy-α-D-ribo-hexopyranoside 
• 117399-48-1 3,4-di-O-benzyl-2,6-dideoxy-β-D-ribo-hexopyranoside 
• 90762-83-7 Methyl 3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside 

Relevant academic research and scientific papers

3-Aminodeoxypyranoses in Glycosylation: Diversity-Oriented Synthesis and Assembly in Oligosaccharides

A concise, diversity-oriented approach for the synthesis of naturally occurring 3-amino- and 3-nitro-2,3,6-trideoxypyranose derivatives and analogues thereof from simple sugars has been developed. In addition, we investigated the synthesis of various 3-aminoglycosyl donors and their application in glycosylation reactions. These studies led to the successful synthesis of a tetrasaccharide containing four different 3-aminosugar components using ortho-alkynylbenzoate donors.

Diversity-Oriented Synthesis of Diol-Based Peptidomimetics as Potential HIV Protease Inhibitors and Antitumor Agents

Peptidomimetic HIV protease inhibitors are an important class of drugs used in the treatment of AIDS. The synthesis of a new type of diol-based peptidomimetics is described. Our route is flexible, uses d-glucal as an inexpensive starting material, and makes minimal use of protection/deprotection cycles. Binding affinities from molecular docking simulations suggest that these compounds are potential inhibitors of HIV protease. Moreover, the antiproliferative activities of compounds 33 a, 35 a, and 35 b on HT-29, M21, and MCF7 cancer cell lines are in the low micromolar range. The results provide a platform that could facilitate the development of medically relevant asymmetrical diol-based peptidomimetics.

Rhodium-Catalyzed Denitrogenative Transannulation of N-Sulfonyl-1,2,3-triazoles with Glycals Giving Pyrroline-Fused N-Glycosides

Described here is a selective synthesis of 2,3-dihydropyrrole-fused N-glycosides through rhodium-catalyzed denitrogenative transannulation of N-sulfonyl-1,2,3-triazoles with glycals. A series of pyrroline-fused N-glycosides are afforded in moderate to exc

Palladium-Catalyzed One-Pot Stereospecific Synthesis of 2-Deoxy Aryl C-Glycosides from Glycals and Anilines in the Presence of tert-Butyl Nitrite

The palladium-catalyzed one-pot synthesis of 2,3-deoxy-3-keto aryl C-glycosides is achieved from glycals and anilines in the presence of tert-butyl nitrite and aqueous HBF 4 under mild conditions. This one-pot method stereospecifically provides α-and β-Aryl glycosides (≥19:1 by NMR) in good yields at room temperature. The configuration at the C-3 position in the glycal determines the anomeric selectivity (i.e., α or β) of the desired products.

Preparation method of 6-bromo-D-glucal

The invention discloses a preparation method of 6-bromo-D-glucal. The reaction route is as follows. The preparation method comprises the following steps: (1), taking glucose as an initial material, and performing reaction in a sodium acetate/acetic anhydride system, so as to form a compound 1; (2), ensuring that the compound 1 is reacted with hydrobromic acid in acetic acid in a methylene dichloride system, so as to form a compound 2; (3), ensuring that the compound 2 is reacted with zinc powder in an acetone/saturated sodium dihydrogen phosphate, so as to form a compound 3; (4), ensuring thatthe compound 3 is reacted in a methanol/sodium methylate system, so as to form D-glucal, and then ensuring that the compound 3 is sequentially reacted with TsCl and acetic anhydride in a pyridine/methylene dichloride system, so as to form a compound 4; (5), ensuring that the compound 4 is reacted with LiBr in a DMSO system, so as to form a compound 5; (6), ensuring that the compound 5 is reacteda the sodium methylate/methanol system, so as to form a compound 6. The preparation method is simple to operate, mild in reaction conditions, cheap and available in raw materials, high in yield, low in cost, and suitable for mass industrial production.

Synthesis of the Hexasaccharide Fragment of Landomycin A Using a Mild, Reagent-Controlled Approach

The synthesis of the hexasaccharide fragment of landomycin A is reported. Using p-toluenesulfonyl chloride mediated dehydrative glycosylation, we constructed the deoxy-sugar linkages in a stereoselective fashion without the need for temporary prosthetic g

Reagent Controlled Direct Dehydrative Glycosylation with 2-Deoxy Sugars: Construction of the Saquayamycin Z Pentasaccharide

The first synthesis of the pentasaccharide fragment of the angucycline antibiotic saquayamycin Z is described. By using our sulfonyl chloride mediated reagent controlled dehydrative glycosylation, we are able to assemble the glycosidic linkages with high

Total Synthesis and Biological Evaluation of the Glycosylated Macrocyclic Antibiotic Mangrolide A

The macrocyclic antibiotic mangrolide A has been described to exhibit potent activity against a number of clinically important Gram-negative pathogens. Reported is the first enantioselective total synthesis of mangrolide A and derivatives. Salient features of this synthesis include a highly convergent macrocycle preparation, stereoselective synthesis of the disaccharide moiety, and two β-selective glycosylations. The synthesis of mangrolide A and its analogues enabled the re-examination of its activity against bacterial pathogens, and only minimal activity was observed.

An efficient method for the synthesis of pyranoid glycals

A simple and efficient procedure was designed for the preparation of pyranoid glycals. In a novel fashion, a series of protected glycopyranosyl bromides underwent reductive elimination in the presence of zinc dust and ammonium chloride in CH3CN at 30-60 °C. The corresponding glycals were obtained with excellent isolated yields (72-96%) in a short time (20-50 min). Furthermore, the transformation was compatible with different protection patterns and conveniently scalable (86% for 45 g acetobromoglucose) which made it very applicable in organic synthesis.

A rapid synthesis of pyranoid glycals promoted by β-cyclodextrin and ultrasound

A convenient and environmentally benign procedure for the synthesis of glycals from glycosyl bromides with very low zinc dust loading (1.5 equiv.) is described. The process is activated by β-cyclodextrin and ultrasound. Based on 19 samples, this method has been demonstrated to be highly effective for a broad range of glycosyl bromides, including acid- or base-sensitive and disaccharide glycosyl bromides. A yield of 85%-96% of glycals was obtained. Copyright