42390-78-3

Basic information

• Product Name: TRIMETHYLSILYL-D(+)TREHALOSE
• Synonyms: TRIMETHYLSILYL-D(+)TREHALOSE
• CAS NO: 42390-78-3
• Molecular Formula: C₃₆H₈₆O₁₁Si₈
• Molecular Weight: 919.75
• Product Categories: Carbohydrates;Carbohydrates A to;Carbohydrates P-ZBiochemicals and Reagents;Disaccharide
• Mol File: 42390-78-3.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 646.8°C at 760 mmHg
• Flash Point: 311.8°C
• Appearance: /
• Density: 0.98g/cm³
• Vapor Pressure: 6.63E-16mmHg at 25°C
• Refractive Index: 1.456
• Storage Temp.: 2-8°C
• CAS DataBase Reference: TRIMETHYLSILYL-D(+)TREHALOSE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLSILYL-D(+)TREHALOSE(42390-78-3)
• EPA Substance Registry System: TRIMETHYLSILYL-D(+)TREHALOSE(42390-78-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 42390-78-3(Hazardous Substances Data)

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

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

Downstream Products

• 222294-64-6 6,6'-di-O-(3-formyl)benzoyl-2,2',3,3',4,4'-hexa-O-trimethylsilyl-α,α-trehalose 
• 1745-65-9 α,α-trehalose 6,6'-diphosphate 
• 4484-88-2 trehalose-6-phosphate 
• 62054-35-7 6-O-<(2RS,3SR)-3-hydroxy-2-tetradecyloctadecanoyl>-α,α-trehalose 
• 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 
• 3317-99-5 6,6'-di-O-palmitoyl-α,α-trehalose 
• 1448242-53-2 3′-O-benzyl-4,6;4′,6′-di-O-benzylidene-2′-O-tert-butyldimethylsilyl-α,α-D-trehalose 
• 1450826-92-2 3′-O-benzyl-4,6;4′,6′-di-O-benzylidene-2′-O-tert-butyldimethylsilyl-2-O-palmitoyl-α,α-D-trehalose 
• 1448242-60-1 3′-O-benzyl-4,6;4′,6′-di-O-benzylidene-2′-O-tert-butyldimethylsilyl-2,3-di-O-palmitoyl-α,α-D-trehalose 
• 1448242-62-3 3′-O-benzyl-4,6;4′,6′-di-O-benzylidene-2′-O-tert-butyldimethylsilyl-3-O-[(S)-2-methyloctadecanoyl]-2-O-palmitoyl-α,α-D-trehalose 
• 1448242-66-7 3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-3-O-[(S)-2-methyloctadecanoyl]-2-O-palmitoyl-α,α-D-trehalose 

Relevant articles and documents

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

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

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.