trehalose 6,6'-dipalmitate

Base Information

• Chemical Name: trehalose 6,6'-dipalmitate
• CAS No.: 3317-99-5
• Molecular Formula: C₄₄H₈₂O₁₃
• Molecular Weight: 819.127
• Mol file: 3317-99-5.mol

Synonyms:Trehalose,6,6'-dipalmitate (7CI,8CI)

Chemical Property of trehalose 6,6'-dipalmitate

Chemical Property:

• Vapor Pressure: 4.46E-34mmHg at 25°C
• Boiling Point: 855.5°Cat760mmHg
• Flash Point: 237.8°C
• PSA: 201.67000
• Density: 1.13g/cm³
• LogP: 6.66720

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of trehalose 6,6'-dipalmitate

There total 8 articles about trehalose 6,6'-dipalmitate 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: 67.0%

TREHALOSE (99-20-7) + 1-hexadecylcarboxylic acid (57-10-3) → 6,6'-di-O-palmitoyl-α,α-trehalose (3317-99-5) + 6-O-(palmitoyl)-α,α-D-trehalose (42939-93-5)

Guidance literature:

With pyridine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; at 20 ℃; for 168h; Concentration; Temperature; Time; Inert atmosphere;

DOI:10.1021/jo302231v

Reference yield: 55.0%

TREHALOSE (99-20-7) + 1-hexadecylcarboxylic acid (57-10-3) → 6,6'-di-O-palmitoyl-α,α-trehalose (3317-99-5)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In N,N-dimethyl-formamide; for 24h; Ambient temperature;

DOI:10.1039/c39840000385

Reference yield:

Hexadecanoic acid (2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-hexadecanoyloxymethyl-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester (138552-19-9) → 6,6'-di-O-palmitoyl-α,α-trehalose (3317-99-5)

Guidance literature:

With trifluoroacetic acid; In water; Yield given; Ambient temperature;

DOI:10.1016/0008-6215(91)84089-W

upstream raw materials:

Hexadecanoic acid (2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-hexadecanoyloxymethyl-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

TREHALOSE

1-hexadecylcarboxylic acid

2,3,4,2’,3’,4’-hexakis-O-(trimethylsilyl)-α,α-trehalose

Refernces

• 1、 Paul, Nawal K.,Twibanire, Jean-D'Amour K.,Grindley, T. Bruce. "Direct synthesis of maradolipids and other trehalose 6-monoesters and 6,6′-diesters". . p. 363 - 369. Retrieved 2013.
• 2、 Dadhich, Ruchika,Mishra, Manjari,Ning, Shangbo,Jana, Santanu,Sarpe, Vikram A.,Mahato, Jaladhar,Duan, Mojie,Kulkarni, Suvarn S.,Kapoor, Shobhna. "A Virulence-Associated Glycolipid with Distinct Conformational Attributes: Impact on Lateral Organization of Host Plasma Membrane, Autophagy, and Signaling". . p. 740 - 750. Retrieved 2020.