104196-14-7

Basic information

• Product Name: 3,3'-neotrehalosadiamine
• Synonyms: 3,3'-neotrehalosadiamine;3-Amino-3-deoxy-β-D-glucopyranosyl 3-amino-3-deoxy-α-D-glucopyranoside;BMY-28251;Bu-2797;Neotrehalosadiamine
• CAS NO: 104196-14-7
• Molecular Formula: C₁₂H₂₄N₂O₉
• Molecular Weight: 340.327
• Mol File: 104196-14-7.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,3'-neotrehalosadiamine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3'-neotrehalosadiamine(104196-14-7)
• EPA Substance Registry System: 3,3'-neotrehalosadiamine(104196-14-7)

Safety Data

• Hazardous Substances Data: 104196-14-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,3'-neotrehalosadiamine is utilized as a key component in the development of new drugs, leveraging its unique structure to enhance the properties and effectiveness of medicinal compounds.
Used in Biotechnology Industry:
In the biotechnology field, 3,3'-neotrehalosadiamine serves as a crucial building block for the creation of novel biocatalysts, which are essential for accelerating and directing biochemical reactions in various industrial processes.
Used in Chemical Synthesis:
3,3'-neotrehalosadiamine is employed as a versatile building block in chemical synthesis, allowing for the construction of a wide array of complex molecules with diverse applications across different industries.

Upstream product

• 185114-94-7 1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose 
• 1417719-76-6 2,4,6-tri-O-acetyl-3-azido-3-deoxy-a-D-glucopyranosyl-(1→1')-2',4',6'-tri-O-acetyl-3'-azido-3'-deoxy-b-D-glucopyranoside 
• 1417719-77-7 3-azido-3-deoxy-α-D-glucopyranosyl-(1→1')-3-azido-30-deoxy-b-D-glucopyranoside 

Relevant articles and documents

Diverse Synthesis of Natural Trehalosamines and Synthetic 1,1′-Disaccharide Aminoglycosides

A general strategy for the diverse synthesis of ten disaccharide aminoglycosides, including natural 2-trehalosamine (1), 3-trehalosamine (2), 4-trehalosamine (3), and neotrehalosyl 3,3′-diamine (8) and synthetic aminoglycosides 4–7, 9, and 10, has been developed. The aminoglycoside compounds feature different anomeric configurations and numbers of amino groups. The key step for the synthesis was the glycosylation coupling of a stereodirecting donor with a configuration-stable TMS glycoside acceptor. Either the donor or acceptor could be substituted with an azido group. The aminoglycosides prepared in the present study were characterized by 1D and 2D NMR spectroscopy.

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.