155417-78-0

Basic information

• Product Name: 3-Azido-3-deoxy-D-galactopyranose 1,2,4,6-tetraacetate
• Synonyms: 3-Azido-3-deoxy-D-galactopyranose 1,2,4,6-tetraacetate
• CAS NO: 155417-78-0
• Molecular Formula: C14H19N3O9
• Molecular Weight: 373.32
• Mol File: 155417-78-0.mol

Chemical Properties

• CAS DataBase Reference: 3-Azido-3-deoxy-D-galactopyranose 1,2,4,6-tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Azido-3-deoxy-D-galactopyranose 1,2,4,6-tetraacetate(155417-78-0)
• EPA Substance Registry System: 3-Azido-3-deoxy-D-galactopyranose 1,2,4,6-tetraacetate(155417-78-0)

Safety Data

• Hazardous Substances Data: 155417-78-0(Hazardous Substances Data)

Upstream product

• 27581-57-3 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 37073-79-3 Methyl-3-nitro-3-desoxy-α-D-mannopyranosid 
• 108-24-7 acetic anhydride 
• 13964-23-3 3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose 
• 104875-44-7 3-azido-3-deoxy-D-glucopyranose 
• 566164-19-0 1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose 
• 620630-83-3 1,2:5,6-di-O-cyclohexylidene-α-D-allofuranose 
• 21870-78-0 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 
• 300572-82-1 3-azido-3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-allofuranose 
• 1048680-81-4 3-azido-3-deoxy-β-D-allofuranose 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 14133-35-8 methyl 3-amino-3-deoxy-α-D-mannopyranoside hydrochloride 
• 64952-23-4 3-hydroxy-2-(1-methoxy-2-oxoethoxy)propanal 
• 945631-54-9 methyl 3-azido-3-deoxy-α-D-mannopyranoside 

Downstream Products

• 1417719-90-4 C₃₄H₄₀N₆O₁₃ 
• 1417719-92-6 2,4,6-tri-O-acetyl-3-azido-3-deoxy-a-D-glucopyranosyl trimethylsilyl triflate 

Relevant articles and documents

Synthesis of a cyclic tetramer of 3-amino-3-deoxyallose with axially oriented amino groups

A linear tetramer of β-(1 → 6)-linked 3-azido-3-deoxy-D-allose containing glycosyl donor and glycosyl acceptor functions in the terminal monosaccharide units was prepared starting from 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose. Cyclization of the linear tetramer under glycosylation conditions afforded the corresponding cyclic tetrasaccharide in 77% yield; its deprotection and reduction of the azido groups resulted in the formation of the cyclic tetramer of 3-amino-3-deoxy-D-allose with axial amino groups, a potential scaffold for the synthesis of tetravalent functional clusters.

LARGE SCALE PROCESS FOR PREPARING 1,2,4, 6-TETRA-0-ACETYL-3-AZID0-3-DE0XY-D-GALACT0PYRAN0SIDE

The present invention relates to a process for preparing a compound of formula (X), wherein said process is suitable for large scale synthesis.

Efficient synthesis of a galectin inhibitor clinical candidate (TD139) using a Payne rearrangement/azidation reaction cascade

Selective galectin inhibitors are valuable research tools and could also be used as drug candidates. In that context, TD139, a thiodigalactoside galectin-3 inhibitor, is currently being evaluated clinically for the treatment of idiopathic pulmonary fibrosis. Herein, we describe a new strategy for the preparation of TD139. Starting from inexpensive levoglucosan, we used a rarely employed reaction cascade: Payne rearrangement/azidation process leading to 3-azido-galactopyranose. The latter intermediate was efficiently converted into TD139 in a few simple and practical steps.

SMALL MOLECULE INHIBITORS OF GALECTIN-3

The present disclosure relates to compounds of formula I, which inhibit Gal-3, and include pharmaceutically acceptable salts, compositions comprising such compounds, and methods using and making such compounds and compositions.

Cluster glycosides and heteroglycoclusters presented in alternative arrangements

Multivalent carbohydrates, or glycoclusters, are useful tools to study glycan-lectin and glycan-enzyme recognition processes and have wide potential therapeutic applicability. Herein, we report the synthesis of novel glycoclusters presenting glucopyranose

Synthesis of azido-deoxy and amino-deoxy glycosides and glycosyl fluorides for screening of glycosidase libraries and assembly of substituted glycosides

Azide- and amine-substituted sugars can be useful tools in the probing of biological systems as well as in the assembly of libraries of derivatives using click chemistry or simple amine coupling approaches. A collection of methylumbelliferyl glycosides of

An efficient method to synthesize novel 5-O-(6′-modified)-mycaminose 14-membered ketolides

A new and facile procedure was developed to synthesize novel 5-O-(6′-modified)-mycaminose 14-membered ketolides by adopting different protective strategies and comparing various glycosylation conditions. Seven trichloroacetimidate donors which had different types of substituent groups at C-6 position were synthesized to couple with the erythronolide. Nine novel 5-O-(6′-modified)-mycaminose 14-membered ketolides were obtained to verify the utility of the method.

Glucose positions affect the phloem mobility of glucose-fipronil conjugates

In our previous work, a glucose-fipronil (GTF) conjugate at the C-1 position was synthesized via click chemistry and a glucose moiety converted a non-phloem-mobile insecticide fipronil into a moderately phloem-mobile insecticide. In the present paper, fipronil was introduced into the C-2, C-3, C-4, and C-6 positions of glucose via click chemistry to obtain four new conjugates and to evaluate the effects of the different glucose isomers on phloem mobility. The phloem mobility of the four new synthetic conjugates and GTF was tested using the Ricinus seedling system. The results confirmed that conjugation of glucose at different positions has a significant influence on the phloem mobility of GTF conjugates.

Glucose positions affect the phloem mobility of glucose-fipronil conjugates

In our previous work, a glucose-fipronil (GTF) conjugate at the C-1 position was synthesized via click chemistry and a glucose moiety converted a non-phloem-mobile insecticide fipronil into a moderately phloem-mobile insecticide. In the present paper, fipronil was introduced into the C-2, C-3, C-4, and C-6 positions of glucose via click chemistry to obtain four new conjugates and to evaluate the effects of the different glucose isomers on phloem mobility. The phloem mobility of the four new synthetic conjugates and GTF was tested using the Ricinus seedling system. The results confirmed that conjugation of glucose at different positions has a significant influence on the phloem mobility of GTF conjugates.

Synthesis of 3,3′-neotrehalosadiamine and related 1,1′-aminodisaccharides using disarmed, armed, and superarmed building blocks

Here we report a high yielding, stereoselective synthesis of the naturally occurring 1,1′-disaccharide neotrehalosadiamine (NTD) and some related analogs. Following an eleven-step sequence, seven of which did not require chromatographic separation, NTD was generated in 60% overall yield from the inexpensive, commercially available precursor 1,2:5,6-di-O-isopropylidene- α-δ-glucofuranose. The key a,b-linkage of NTD was formed in a highly stereoselective manner by taking advantage of the participating effect of the acyl group at O-2 of the donor glycoside. The influence of electronic effects of disarmed, armed, and superarmed glycosyl donors and acceptors on the outcome of 1,1′-glycosidation was also observed. Antibacterial studies using NTD and its analogs show detectable but weak antistaphylococcal activity.