51855-99-3

Basic information

• Product Name: 4-trehalosamine
• Synonyms: 4-trehalosamine;4-Amino-4-deoxy-α-D-glucopyranosyl α-D-glucopyranoside;α-D-Glucopyranosyl 4-amino-4-deoxy-α-D-glucopyranoside
• CAS NO: 51855-99-3
• Molecular Formula: C₁₂H₂₃NO₁₀
• Molecular Weight: 341.311
• Mol File: 51855-99-3.mol

Chemical Properties

• Boiling Point: 671.7°Cat760mmHg
• Flash Point: 360°C
• Appearance: /
• Density: 1.7g/cm³
• Vapor Pressure: 6.45E-21mmHg at 25°C
• Refractive Index: 1.649
• CAS DataBase Reference: 4-trehalosamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-trehalosamine(51855-99-3)
• EPA Substance Registry System: 4-trehalosamine(51855-99-3)

Safety Data

• Hazardous Substances Data: 51855-99-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H23NO10/c13-5-3(1-14)21-11(9(19)7(5)17)23-12-10(20)8(18)6(16)4(2-15)22-12/h3-12,14-20H,1-2,13H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1

Upstream product

• 129785-35-9 4-azido-4-deoxy-α-D-glucopyranosyl α-D-glucopyranoside 
• 1456898-46-6 4-azido-2,3,6,2',3'-penta-O-(benzyl)-4',6'-O-benzylidene-α,α-D-trehalose 
• 132183-33-6 2,3,6-tri-O-benzyl-α-D-glucopyranosyl 2,3,6-tri-O-benzylidene-α-D-glucopyranoside 
• 129727-86-2 C₄₈H₈₀O₂₀S 
• 129727-79-3 2,3,6-tri-O-pivaloyl-α-D-glucopyranosyl 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranoside 
• 61207-38-3 2,3,6-Tri-O-benzoyl-α-D-glucopyranosyl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside 
• 129828-57-5 4-azido-4-deoxy-2,3,6-tri-O-pivaloyl-α-D-glucopyranosyl 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranoside 
• 129727-88-4 4-chloro-4-deoxy-2,3,6-tri-O-pivaloyl-α-D-galactopyranosyl 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranoside 
• 148260-64-4 4-Azido-2,3,6-tri-O-benzoyl-4-deoxy-α-D-glucopyranosyl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside 
• 148180-47-6 4-Deoxy-4-trifluoroacetamido-α-D-glucopyranosyl α-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.

Visualization of mycobacterial membrane dynamics in live cells

Mycobacteria are endowed with a highly impermeable mycomembrane that confers intrinsic resistance to many antibiotics. Several unique mycomembrane glycolipids have been isolated and structurally characterized, but the underlying organization and dynamics of glycolipids within the cell envelope remain poorly understood. We report here a study of mycomembrane dynamics that was enabled by trehalose-fluorophore conjugates capable of labeling trehalose glycolipids in live actinomycetes. We identified fluorescein-trehalose analogues that are metabolically incorporated into the trehalose mycolates of representative Mycobacterium, Corynebacterium, Nocardia, and Rhodococcus species. Using these probes, we studied the mobilities of labeled glycolipids by time-lapse microscopy and fluorescence recovery after photobleaching experiments and found that mycomembrane fluidity varies widely across species and correlates with mycolic acid structure. Finally, we discovered that treatment of mycobacteria with ethambutol, a front-line tuberculosis (TB) drug, significantly increases mycomembrane fluidity. These findings enhance our understanding of mycobacterial cell envelope structure and dynamics and have implications for development of TB drug cocktails.

Desymmetrization of trehalose via regioselective DIBAL reductive ring opening of benzylidene and substituted benzylidene acetals

Trehalose dibenzylidene and substituted dibenzylidene acetals were reductively opened either at O6 or O4 in a regioselective manner by using a DIBAL stock solution prepared in toluene or dichloromethane, respectively, to achieve desymmetrization of the trehalose core. The method was applied to synthesize various biologically important unsymmetrically substituted trehalose glycoconjugates, including a mycobacterial trisaccharide, a 4-epi-trehalosamine analog and a maradolipid.

An improved synthesis of 4-azido-4-deoxy- and 4-amino-4-deoxy-α,α-trehalose and their epimers

The order of esterification of the eight hydroxyl groups of α,α-trehalose is HO-6,6' > HO-2,2' > HO-3,3' > HO-4,4'.Under the appropriate conditions of benzoylation, the heptabenzoate with HO-4' free was obtained in good yield (58percent), along with the o

Syntheses of hepta-, hexa-, and penta-pivalates of trehalose by selective pivaloylation

The order of esterification of the eight hydroxyl groups of trehalose with pivaloyl chloride is HO-6,6' > HO-2,2' > HO-3,3' > HO-4 4'.Under the appropriate conditions of pivaloylation, heptapivalates with either HO-4 or HO-3 free, hexapivalates with eithe