(2S,3S,4R)-2-Azido-1,3,4-octadecanetriol

Base Information

• Chemical Name: (2S,3S,4R)-2-Azido-1,3,4-octadecanetriol
• CAS No.: 117168-59-9
• Molecular Formula: C18H37N3O3
• Molecular Weight: 343.51
• Mol file: 117168-59-9.mol

Synonyms:(2S,3S,4R)-2-azido-3,4-O-isopropylidene-1,3,4-octadecanetriol;(2S,3S,4R)-2-AZIDO-1,3,4-OCTADECANETRIOL;2-O-azido-D-ribo-1,2,3,4-octadecantetrol;(2S,3S,4R)-2-azidooctadecane-1,3,4-triol;(2S,3S,4R)-2-Azido-octadecane-1,3,4-triol;(2S,3S,4S)-2-azidoactadecan-1,3,4-triol;2-azido-D-ribo-1,3,4-octadecanetriol;

Chemical Property of (2S,3S,4R)-2-Azido-1,3,4-octadecanetriol

Chemical Property:

• PSA: 110.44000
• LogP: 3.92336
• Solubility.: Dichloromethane, Methanol

Purity/Quality:

99% ^*data from raw suppliers

(2S,3S,4R)-2-Azido-1,3,4-octadecanetriol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S,3S,4R)-2-Azido-1,3,4-octadecanetriol can control immune activity with light to improve the immunostimulatory activity of α-?galactosylceramide.

Technology Process of (2S,3S,4R)-2-Azido-1,3,4-octadecanetriol

There total 48 articles about (2S,3S,4R)-2-Azido-1,3,4-octadecanetriol 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: 100.0%

D-ribo-phytosphingosine (554-62-1) → (2S,3S,4R)-2-azido-1,3,4-octadecanetriol (117168-59-9)

Guidance literature:

With triflic azide; potassium carbonate; copper(II) sulfate; In methanol; dichloromethane; water; at 20 ℃; for 18h;

DOI:10.1021/acsmedchemlett.7b00107

Reference yield: 100.0%

(2S,3S,4R)-2-aminooctadecane-1,3,4-triol hydrochloride (77844-50-9) → (2S,3S,4R)-2-azido-1,3,4-octadecanetriol (117168-59-9)

Guidance literature:

With triflic azide; copper(II) sulfate; In dichloromethane; water;

DOI:10.3998/ark.5550190.0014.224

Reference yield: 100.0%

(2S,3S,4R)-1,3,4-tri-O-acetyl-2-azido-1,3,4-octadecanetriol (164385-82-4) → (2S,3S,4R)-2-azido-1,3,4-octadecanetriol (117168-59-9)

Guidance literature:

With sodium methylate; In methanol; for 2h;

DOI:10.1016/S0957-4166(00)86295-3

upstream raw materials:

2-azido-1,3-O-benzylidene-D-ribo-1,3,4-octadecanetriol

(4S,5S)-5-Azido-4-((R)-1-methoxymethoxy-pentadecyl)-2,2-dimethyl-[1,3]dioxane

(2R,3R,4R)-1,3,4-trihydroxyoctadecan-2-yl methanesulfonate

(2S,3S,4R)-1,3,4-tri-O-acetyl-2-azido-1,3,4-octadecanetriol

Downstream raw materials:

(2S,3S,4R)-2-azido-1-(trityloxy)octadecane-3,4-diol

(2S,3S,4R)-2-azido-1-benzyloxyoctadecane-3,4-diol

(2S,3S,4R)-2-azido-1,3-di(benzyloxy)octadecan-4-ol

(2S,3S,4R)-1,3,4-tri-O-benzyl-2-azido-1,3,4-octadecanetriol

Refernces

• 1、 Li, Tingshen,Wang, Xiaodan,Dong, Peijie,Yu, Peng,Zhang, Yongmin,Meng, Xin. "Chemoenzymatic synthesis and biological evaluation of ganglioside GM3 and lyso-GM3 as potential agents for cancer therapy". . . Retrieved 2021/09/07.
• 2、 -. "Ganglioside GM3 and/or analogue thereof, synthesis method and application of ganglioside GM3 and/or analogue thereof". Paragraph 0153; 0162-0165. . Retrieved 2020/06/20.