TRIMETHYLSILYL-D(+)TREHALOSE

Base Information

• Chemical Name: TRIMETHYLSILYL-D(+)TREHALOSE
• CAS No.: 42390-78-3
• Molecular Formula: C36H86 O11 Si8
• Molecular Weight: 919.756
• Mol file: 42390-78-3.mol

Synonyms:Octa(trimethylsilyl)trehalose

Chemical Property of TRIMETHYLSILYL-D(+)TREHALOSE

Chemical Property:

• Vapor Pressure: 6.63E-16mmHg at 25°C
• Refractive Index: 1.456
• Boiling Point: 646.8°C at 760 mmHg
• Flash Point: 311.8°C
• PSA: 101.53000
• Density: 0.98g/cm³
• LogP: 9.47640
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

TRIMETHYLSILYL-D(+)-TREHALOSE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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))

Technology Process of TRIMETHYLSILYL-D(+)TREHALOSE

There total 6 articles about TRIMETHYLSILYL-D(+)TREHALOSE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

TREHALOSE (99-20-7) + N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) → 2,3,4,6,2',3',4',6'-octa-O-trimethylsilyl-α,α-D-trehalose (42390-78-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0008-6215(92)84254-P

Reference yield: 96.0%

chloro-trimethyl-silane (75-77-4) + TREHALOSE (99-20-7) → 2,3,4,6,2',3',4',6'-octa-O-trimethylsilyl-α,α-D-trehalose (42390-78-3)

Guidance literature:

With pyridine; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo4012255

Reference yield: 96.0%

TREHALOSE (99-20-7) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 2,3,4,6,2',3',4',6'-octa-O-trimethylsilyl-α,α-D-trehalose (42390-78-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

DOI:10.1002/ejoc.201101267

upstream raw materials:

TREHALOSE

N,O-bis-(trimethylsilyl)-acetamide

1,1,1,3,3,3-hexamethyl-disilazane

chloro-trimethyl-silane

Downstream raw materials:

6,6'-di-O-(3-formyl)benzoyl-2,2',3,3',4,4'-hexa-O-trimethylsilyl-α,α-trehalose

α,α-trehalose 6,6'-diphosphate

trehalose-6-phosphate

6-O-<(2RS,3SR)-3-hydroxy-2-tetradecyloctadecanoyl>-α,α-trehalose

Refernces

• 1、 Kobayashi, Kurumi,Saito, Rumiko,Udagawa, Kaori,Miyano-Kurosaki, Naoko,Asano, Naoto,Iwanaga, Tetsuo,Teramoto, Naozumi,Shimasaki, Toshiaki,Shibata, Mitsuhiro. "Synthesis of 6,6′-Bis(O-4-arylethynylbenzoyl)-α,α-Trehaloses and Their Utilization as Fluorescent Probes for Cellular Imaging". . p. 3444 - 3453. Retrieved 2018.
• 2、 Sarpe, Vikram A.,Kulkarni, Suvarn S.. "Synthesis of maradolipid". . p. 6866 - 6870. Retrieved 2011.
• 3、 Colombo, Eleonora,Biocotino, Michele,Frapporti, Giulia,Randazzo, Pietro,Christodoulou, Michael S.,Piccoli, Giovanni,Polito, Laura,Seneci, Pierfausto,Passarella, Daniele. "Nanolipid-trehalose conjugates and nano-assemblies as putative autophagy inducers". . . Retrieved 2019/09/10.