42390-78-3

Usage

Uses

α,α-Trehalose octa-O-(Trimethylsilyl) is an intermediate in the synthesis of Trehalose 6-Phosphate Dipotassium Salt (T718715), an intermediate in the synthesis of D-(+)-Trehalose (T718750), a disaccharide composed of two α-glucose units. D-(+)-Trehalose is used in many processed foods as well as in biopharmaceutical monoclonal antibody formulations. When plants’ sugar levels are low, they reduce their investment in fatty acid synthesis. Trehalose 6-phoshate (T6P) regulates oil synthesis in plants. (Chem. and Eng. News p. 9 Oct. 1, (2018))

InChI:InChI=1/C36H86O11Si8/c1-48(2,3)37-25-27-29(42-50(7,8)9)31(44-52(13,14)15)33(46-54(19,20)21)35(39-27)41-36-34(47-55(22,23)24)32(45-53(16,17)18)30(43-51(10,11)12)28(40-36)26-38-49(4,5)6/h27-36H,25-26H2,1-24H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 99-20-7 TREHALOSE 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 

Downstream Products

• 1272439-28-7 3,6,3',6'-tetra-O-benzyl-α,α-D-trehalose 
• 1272439-40-3 2,4,2',4'-tetra-O-acetyl-3,6,3',6'-tetra-O-benzyl-α,α-D-trehalose 
• 127072-98-4 2,2'-di-O-acetyl-3,3'-di-o-benzyl-4,6,4',6'-di-o-benzylidene-α,α'-D-trehalose 
• 127072-92-8 3,3'-di-o-benzyl-4,6,4',6'-di-o-benzylidene-α,α'-D-trehalose 
• 62054-35-7 6-O-<(2RS,3SR)-3-hydroxy-2-tetradecyloctadecanoyl>-α,α-trehalose 
• 4484-88-2 trehalose-6-phosphate 
• 1745-65-9 α,α-trehalose 6,6'-diphosphate 
• 222294-64-6 6,6'-di-O-(3-formyl)benzoyl-2,2',3,3',4,4'-hexa-O-trimethylsilyl-α,α-trehalose 
• 1404341-61-2 6-O-bis[1-(2-nitrophenyl)ethoxyphosphoryl]-D-trehalose 
• 1404341-58-7 6-O-bis-(4,5-dimethoxy-2-nitrobenzyloxyphosphoryl)-D-trehalose 
• 1404341-55-4 6-O-bis-(2-nitrobenzyloxyphosphoryl)-D-trehalose 
• 1253891-13-2 6-O-diphenoxyphosphoryl-α,α-D-trehalose 
• 18933-88-5 6-azido-6-deoxy-α-D-glucopyranosyl-(1→1)-6-azido-6-deoxy-α-D-glucopyranoside 

Relevant academic research and scientific papers

Engineering the Mycomembrane of Live Mycobacteria with an Expanded Set of Trehalose Monomycolate Analogues

Mycobacteria and related organisms in the Corynebacterineae suborder are characterized by a distinctive outer membrane referred to as the mycomembrane. Biosynthesis of the mycomembrane occurs through an essential process called mycoloylation, which involv

Synthesis of 6,6′-Bis(O-4-arylethynylbenzoyl)-α,α-Trehaloses and Their Utilization as Fluorescent Probes for Cellular Imaging

A series of 6,6′-bis(O-4-arylethynylbenzoyl)-α,α-trehaloses (aryl groups; 1a: 1-pyrenyl, 1b: 9-anthryl, 1c: phenyl) were synthesized and fully characterized. Their photophysical properties were investigated by UV/Vis/fluorescence spectroscopy, and were rationalized by TDDFT calculations. Moreover, the emission maxima of 1a and 1b in THF/H2O considerably shifted to a longer wavelength region with increasing H2O fraction owing to the formation of excimers. The pyrenyl derivative 1a was efficiently taken into HeLa CD4+ human cervical cancer cells and emitted bright green fluorescence.

Synthesis of maradolipid

The first synthesis of maradolipid, a unique dissymmetrically 6,6′-di-O-acylated trehalose glycolipid isolated from C. elegans, is accomplished in five steps starting from trehalose in 45% overall yield. The short synthesis relies on dissymmetrization of trehalose core via regioselective acylation of a 2,3,4,2′,3′,4′-hexa-O-TMS trehalose 6,6′-diol derivative as a key step.

Trehalose-based neuroprotective autophagy inducers

A small set of trehalose-centered putative autophagy inducers was rationally designed and synthesized, with the aim to identify more potent and bioavailable autophagy inducers than free trehalose, and to acquire information about their molecular mechanism

Nanolipid-trehalose conjugates and nano-assemblies as putative autophagy inducers

The disaccharide trehalose is an autophagy inducer, but its pharmacological application is severely limited by its poor pharmacokinetics properties. Thus, trehalose was coupled via suitable spacers with squalene (in 1:2 and 1:1 stoichiometry) and with betulinic acid (1:2 stoichiometry), in order to yield the corresponding nanolipid-trehalose conjugates 1-Sq-mono, 2-Sq-bis and 3-Be-mono. The conjugates were assembled to produce the corresponding nano-assemblies (NAs) Sq-NA1, Sq-NA2 and Be-NA3. The synthetic and assembly protocols are described in detail. The resulting NAs were characterized in terms of loading and structure, and tested in vitro for their capability to induce autophagy. Our results are presented and thoroughly commented upon.

Lipid length and iso-branching of trehalose diesters influences Mincle agonist activity

We report on the efficient synthesis of linear trehalose diesters (TDEs) and iso-branched TDEs (maradolipids or iso-TDEs) and their ability to activate bone marrow-derived macrophages (BMDMs) as determined by cytokine (IL-1β IL-12, IL-6, IL-10) and chemokine (MIP-2) production. Both classes of TDEs were found to activate BMDMs in a Mincle-dependent manner, with longer-chain (≥C18) lipids leading to a robust inflammatory response. On the whole, the iso-branched TDEs led to greater cytokine production and a faster immune response when compared to their linear counterparts. Moreover, C12-TDE and iso-C12-TDE elicited the production of MIP-2 by BMDMs, thereby providing the first example of TDEs with a chain length of ≤ C12 leading to a Mincle-dependent immune response and one that is less inflammatory in nature.

BIODEGRADABLE TREHALOSE GLYCOPOLYMERS

Structures and methods of making biodegradable trehalose co-polymers are disclosed. Specifically, biodegradable trehalose co-polymers consist of the general structure R5-[R1R2C - CR3R4]n-[DG]m/s

Synthesis of a mycobacterium tuberculosis tetra-acylated sulfolipid analogue and characterization of the chiral acyl chains using anisotropic NAD 2D-NMR spectroscopy

Tetra-O-acylated sulfolipids are metabolites found in the cell wall of Mycobacterium tuberculosis, the causative agent of tuberculosis. Their role in pathogenesis remains, however, undefined. Here we describe a novel access to model tetra-O-acylated treha

Synthesis and structure - Activity relationships studies of brartemicin analogs as anti-invasive agents

Brartemicin is a trehalose-based inhibitor of tumor cell invasion produced by the actinomycete of the genus Nonomuraea. In order to find more potent anti-invasive agents and study the structure-activity relationships, a series of 19 brartemicin analogs we

Simple one-pot regioselective 6-O-phosphorylation of carbohydrates and trehalose desymmetrization

Biologically essential carbohydrate 6-phosphates, especially trehalose 6-phosphate, can be synthesized easily in excellent overall yields in 2 steps involving minimum protecting group manipulations. We can cleave the diphenylphosphate group for further synthetic objectives.