3317-99-5

Basic information

• Product Name: trehalose 6,6'-dipalmitate
• Synonyms: trehalose 6,6'-dipalmitate
• CAS NO: 3317-99-5
• Molecular Formula: C44H82 O13
• Molecular Weight: 0
• Mol File: 3317-99-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 855.5°Cat760mmHg
• Flash Point: 237.8°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 4.46E-34mmHg at 25°C
• Refractive Index: 1.523
• CAS DataBase Reference: trehalose 6,6'-dipalmitate(CAS DataBase Reference)
• NIST Chemistry Reference: trehalose 6,6'-dipalmitate(3317-99-5)
• EPA Substance Registry System: trehalose 6,6'-dipalmitate(3317-99-5)

Safety Data

• Hazardous Substances Data: 3317-99-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C44H82O13/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-35(45)53-31-33-37(47)39(49)41(51)43(55-33)57-44-42(52)40(50)38(48)34(56-44)32-54-36(46)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33-34,37-44,47-52H,3-32H2,1-2H3/t33-,34-,37-,38-,39+,40+,41-,42-,43-,44-/m1/s1

Upstream product

• 59578-12-0 2,3,4,2’,3’,4’-hexakis-O-(trimethylsilyl)-α,α-trehalose 
• 99-20-7 TREHALOSE 
• 57-10-3 1-hexadecylcarboxylic acid 
• 42390-78-3 2,3,4,6,2',3',4',6'-octa-O-trimethylsilyl-α,α-D-trehalose 
• 138552-19-9 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 

Relevant articles and documents

Synthesis of ten members of the maradolipid family; Novel diacyltrehalose glycolipids from caenorhabditis elegans

The synthesis of ten members of the maradolipid family is described using a direct route starting from trehalose. Georg Thieme Verlag Stuttgart · New York.

Improved Synthesis of 'Cord Factor' Analogues

Treatment of trehalose or sucrose with triphenylphosphine, di-isopropyl azodicarboxylate, and palmitic acid results in the formation of the corresponding 6,6'-dipalmitates-analogues of 'cord factor' - in good yield under exceptionally mild conditions.

An improved synthesis of trehalose 6-mono- and 6,6'-di-corynomycolates and related esters

A simplified synthesis of 6-mono- and 6,6'-di-corynomycolate esters of α,α-trehalose, and related compounds, was achieved by coupling the (hydroxyl-protected) acids to the partially trimethylsilylated sugar in the presence of dicyclohexylcarbodiimide and 4-dimethylaminopyridine.As acid reactants, (2-RS,3-RS)-3-hydroxy-2-tetradecyloctadecanoic acid (DL-corynomycolic acid) and its 2RS, 3SR diastereomer were prepared from methyl palmitate by sequential Claisen condensation, reduction, chromatographic separation, and saponification.Reaction with tert-butylchlorodimethylsilane (imidazole) gave the disubstituted ether-esters, which were converted into the required 3-tert-butyldimethylsilyl ethers by partial hydrolysis. 6-Linked monocorynomycolate was obtained in excellent yield (78percent) from the reaction of the RS,SR acid with the known heptakis-O-(trimethylsilyl)trehalose, and in good yield from equimolar portions of RS,RS acid and hexakis-O-(trimethylsilyl)trehalose.An excess (2.5-molar portions) of the RS,RS acid gave the 6,6'-diester (69percent).The mono- and di-palmitate were similarly obtained from (Me3Si)6-trehalose.The mono (RS,RS)-(Me3Si)6-trehalose coupling product was partially resolved on a silica gel column into its RR and SS diastereomers, the former corresponding to the naturally occurring trehalose monocorynomycolate.All coupling products were deprotected to free trehalose esters by treatment first with K2CO3 in methanol, then tetrabutylammonium fluoride-trifluoracetic acid in oxolane.