[(S)-2-azido-2-((4S,5R)-2,2-dioxo-5-tetradecyl-2λ⁶-[1,3,2]dioxathiolan-4-yl)ethoxy]-tert-butyldiphenylsilane

Base Information

• Chemical Name: [(S)-2-azido-2-((4S,5R)-2,2-dioxo-5-tetradecyl-2λ⁶-[1,3,2]dioxathiolan-4-yl)ethoxy]-tert-butyldiphenylsilane
• CAS No.: 916159-69-8
• Molecular Formula: C₃₄H₅₃N₃O₅SSi
• Molecular Weight: 643.963
• Mol file: 916159-69-8.mol

Synonyms:[(S)-2-azido-2-((4S,5R)-2,2-dioxo-5-tetradecyl-2λ⁶-[1,3,2]dioxathiolan-4-yl)ethoxy]-tert-butyldiphenylsilane

Chemical Property of [(S)-2-azido-2-((4S,5R)-2,2-dioxo-5-tetradecyl-2λ⁶-[1,3,2]dioxathiolan-4-yl)ethoxy]-tert-butyldiphenylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(S)-2-azido-2-((4S,5R)-2,2-dioxo-5-tetradecyl-2λ⁶-[1,3,2]dioxathiolan-4-yl)ethoxy]-tert-butyldiphenylsilane

There total 4 articles about [(S)-2-azido-2-((4S,5R)-2,2-dioxo-5-tetradecyl-2λ⁶-[1,3,2]dioxathiolan-4-yl)ethoxy]-tert-butyldiphenylsilane 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: 89.0%

(2S,3S,4R)-2-azido-1-(tert-butyldiphenylsilyloxy)octadecane-3,4-diol (916159-68-7) → [(S)-2-azido-2-((4S,5R)-2,2-dioxo-5-tetradecyl-2λ6-[1,3,2]dioxathiolan-4-yl)ethoxy]-tert-butyldiphenylsilane (916159-69-8)

Guidance literature:

(2S,3S,4R)-2-azido-1-(tert-butyldiphenylsilyloxy)octadecane-3,4-diol; With sulfuryl dichloride; triethylamine; In dichloromethane; at 0 ℃;

With sodium periodate; ruthenium(III) chloride trihydrate; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 2h;

DOI:10.1039/c7cc04090c

Reference yield:

D-ribo-phytosphingosine (554-62-1) → [(S)-2-azido-2-((4S,5R)-2,2-dioxo-5-tetradecyl-2λ6-[1,3,2]dioxathiolan-4-yl)ethoxy]-tert-butyldiphenylsilane (916159-69-8)

Guidance literature:

Multi-step reaction with 4 steps

1: trifluoromethanesulfonyl azide; potassium carbonate; copper(II) sulfate / methanol; H₂O; CH₂Cl₂ / 3 h / 20 °C

2: 87 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂; dimethylformamide / 24 h / 20 °C

3: thionyl chloride; triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

4: 1.09 g / sodium periodate; ruthenium(III) chloride trihydrate / CCl₄; acetonitrile; H₂O / 2 h / 20 °C

With dmap; ruthenium trichloride; sodium periodate; thionyl chloride; triflic azide; potassium carbonate; copper(II) sulfate; triethylamine; In methanol; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo0614543

Reference yield:

(2S,3S,4R)-2-azido-1,3,4-octadecanetriol (117168-59-9) → [(S)-2-azido-2-((4S,5R)-2,2-dioxo-5-tetradecyl-2λ6-[1,3,2]dioxathiolan-4-yl)ethoxy]-tert-butyldiphenylsilane (916159-69-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂; dimethylformamide / 24 h / 20 °C

2: thionyl chloride; triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

3: 1.09 g / sodium periodate; ruthenium(III) chloride trihydrate / CCl₄; acetonitrile; H₂O / 2 h / 20 °C

With dmap; ruthenium trichloride; sodium periodate; thionyl chloride; triethylamine; In tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo0614543

upstream raw materials:

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

D-ribo-phytosphingosine

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

Downstream raw materials:

(2S,3R)-(E)-2-azido-1-(tert-butyldiphenylsilyloxy)octadec-4-en-3-ol

(2S,3S,4S)-2-azido-1-(tert-butyldiphenylsilyloxy)-4-iodooctadecan-3-ol

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

2-azido-sphingosine

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、 Santra, Abhishek,Li, Yanhong,Yu, Hai,Slack, Teri J.,Wang, Peng George,Chen, Xi. "Highly efficient chemoenzymatic synthesis and facile purification of α-Gal pentasaccharyl ceramide Galα3nLc4βCer". . p. 8280 - 8283. Retrieved 2017/07/26.