(4S,5R)-4-((S)-1-Azido-2-trityloxy-ethyl)-5-tetradecyl-[1,3,2]dioxathiolane 2,2-dioxide

Base Information

• Chemical Name: (4S,5R)-4-((S)-1-Azido-2-trityloxy-ethyl)-5-tetradecyl-[1,3,2]dioxathiolane 2,2-dioxide
• CAS No.: 928634-52-0
• Molecular Formula: C₃₇H₄₉N₃O₅S
• Molecular Weight: 647.879
• Mol file: 928634-52-0.mol

Synonyms:(4S,5R)-4-((S)-1-Azido-2-trityloxy-ethyl)-5-tetradecyl-[1,3,2]dioxathiolane 2,2-dioxide

Chemical Property of (4S,5R)-4-((S)-1-Azido-2-trityloxy-ethyl)-5-tetradecyl-[1,3,2]dioxathiolane 2,2-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-4-((S)-1-Azido-2-trityloxy-ethyl)-5-tetradecyl-[1,3,2]dioxathiolane 2,2-dioxide

There total 5 articles about (4S,5R)-4-((S)-1-Azido-2-trityloxy-ethyl)-5-tetradecyl-[1,3,2]dioxathiolane 2,2-dioxide 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:

(4S,5R)-4-((S)-1-Azido-2-trityloxy-ethyl)-5-tetradecyl-[1,3,2]dioxathiolane 2-oxide → (4S,5R)-4-((S)-1-Azido-2-trityloxy-ethyl)-5-tetradecyl-[1,3,2]dioxathiolane 2,2-dioxide (928634-52-0)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 20 ℃;

DOI:10.1021/jo0614543

Reference yield:

D-ribo-phytosphingosine (554-62-1) → (4S,5R)-4-((S)-1-Azido-2-trityloxy-ethyl)-5-tetradecyl-[1,3,2]dioxathiolane 2,2-dioxide (928634-52-0)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 84 percent / pyridine / CH₂Cl₂ / 16 h

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

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

With pyridine; ruthenium trichloride; sodium periodate; thionyl chloride; triflic azide; potassium carbonate; copper(II) sulfate; triethylamine; In methanol; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/jo0614543

Reference yield:

trityl chloride (76-83-5) → (4S,5R)-4-((S)-1-Azido-2-trityloxy-ethyl)-5-tetradecyl-[1,3,2]dioxathiolane 2,2-dioxide (928634-52-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / pyridine / CH₂Cl₂ / 16 h

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

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

With pyridine; ruthenium trichloride; sodium periodate; thionyl chloride; triethylamine; In tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/jo0614543

upstream raw materials:

D-ribo-phytosphingosine

trityl chloride

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

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

Downstream raw materials:

2-azido-sphingosine

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