Propargyl-PEG5-tetra-Ac-beta-D-glucose

Base Information

• Chemical Name: Propargyl-PEG5-tetra-Ac-beta-D-glucose
• CAS No.: 1360446-31-6
• Molecular Formula: C₂₅H₃₈O₁₄
• Molecular Weight: 562.568
• Mol file: 1360446-31-6.mol

Synonyms:

Chemical Property of Propargyl-PEG5-tetra-Ac-beta-D-glucose

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Propargyl-PEG5-tetra-Ac-beta-D-glucose 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Propargyl-PEG5-tetra-Ac-beta-D-glucose is a Click Chemistry-ready crosslinker containing a propargyl group and beta-D-glucose. The propargyl groups can react with azide-bearing compounds or biomolecules via copper catalyzed azide-alkyne Click Chemistry to yield stable triazole linkages. D-glucose increases solubility in aqueous media and increases the selectivity of the PEGylation reaction.

Technology Process of Propargyl-PEG5-tetra-Ac-beta-D-glucose

There total 6 articles about Propargyl-PEG5-tetra-Ac-beta-D-glucose 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: 83.0%

3,6,9,12-tetraoxapentadec-14-yn-1-ol (87450-10-0) + peracetylated β-D-glucose (14199-53-2,51844-36-1,61403-03-0,67322-04-7,70613-81-9,70613-82-0,132561-89-8) → 3,6,9,12-tetraoxapentadec-14-ynyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (1397682-61-9,1360446-31-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/c2cc17458h

Reference yield: 65.0%

3,6,9,12-tetraoxapentadec-14-yn-1-ol (87450-10-0) + 2,3,4,6-tetra-O-acetyl-α/β-D-mannopyranoside trichloroacetimidate → 3,6,9,12-tetraoxapentadec-14-ynyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (1013921-31-7,1360446-31-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30 - 20 ℃;

DOI:10.1039/b716113a

Reference yield: 35.0%

D-galactose pentaacetate (25878-60-8) + 3,6,9,12-tetraoxapentadec-14-yn-1-ol (87450-10-0) → 3,6,9,12-tetraoxapentadec-14-ynyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (1397682-61-9,1360446-31-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.inorgchem.8b01335

upstream raw materials:

3,6,9,12-tetraoxapentadec-14-yn-1-ol

peracetylated β-D-glucose

β-D-galactose peracetate

Tetraethylene glycol

Downstream raw materials:

{2-[2-(2-(2-propyn-1-yloxy)ethoxy)ethoxy]ethoxy}ethyl-β-D-galactopyranoside

C₁₇H₃₀O₁₀

Refernces

• 1、 Chen, Shiguang,Fang, Yanfen,Zhu, Qiwen,Zhang, Wanli,Zhang, Xiongwen,Lu, Wei. "NIR fluorescent DCPO glucose analogues and their application in cancer cell imaging". . p. 81894 - 81901. Retrieved 2016.
• 2、 Fernandes, Antony,Viterisi, Aurelien,Aucagne, Vincent,Leigh, David A.,Papot, Sebastien. "Second generation specific-enzyme-activated rotaxane propeptides". supporting information; experimental part. p. 2083 - 2085. Retrieved 2012/03/26.