tert-butyl ((2S,3S,4R)-3,4-dihydroxy-1-(trityloxy)octadecan-2-yl)carbamate

Base Information

• Chemical Name: tert-butyl ((2S,3S,4R)-3,4-dihydroxy-1-(trityloxy)octadecan-2-yl)carbamate
• CAS No.: 1340475-39-9
• Molecular Formula: C₄₂H₆₁NO₅
• Molecular Weight: 659.95
• Mol file: 1340475-39-9.mol

Synonyms:tert-butyl ((2S,3S,4R)-3,4-dihydroxy-1-(trityloxy)octadecan-2-yl)carbamate

Chemical Property of tert-butyl ((2S,3S,4R)-3,4-dihydroxy-1-(trityloxy)octadecan-2-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl ((2S,3S,4R)-3,4-dihydroxy-1-(trityloxy)octadecan-2-yl)carbamate

There total 2 articles about tert-butyl ((2S,3S,4R)-3,4-dihydroxy-1-(trityloxy)octadecan-2-yl)carbamate 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: 95.0%

trityl chloride (76-83-5) + tert-butyl [(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate (175696-50-1) → tert-butyl ((2S,3S,4R)-3,4-dihydroxy-1-(trityloxy)octadecan-2-yl)carbamate (1340475-39-9)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c1ob05920c

Reference yield: 82.0%

D-ribo-phytosphingosine (554-62-1) + di-tert-butyl dicarbonate (24424-99-5) + trityl chloride (76-83-5) → tert-butyl ((2S,3S,4R)-3,4-dihydroxy-1-(trityloxy)octadecan-2-yl)carbamate (1340475-39-9)

Guidance literature:

D-ribo-phytosphingosine; di-tert-butyl dicarbonate; In tetrahydrofuran; at 20 ℃; for 12h; Inert atmosphere; Schlenk technique;

trityl chloride; With pyridine; dmap; In tetrahydrofuran; at 80 ℃; for 12h; Inert atmosphere; Schlenk technique;

trityl chloride; In tetrahydrofuran; for 2h; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201905279

Reference yield: 95.0%

tert-butyl ((2S,3S,4R)-3,4-dihydroxy-1-(trityloxy)octadecan-2-yl)carbamate (1340475-39-9) → (4S,5S)-5-((R)-1-hydroxypentadecyl)-4-(trityloxymethyl)oxazolidin-2-one (1340475-40-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 0.5h; regioselective reaction; Inert atmosphere;

DOI:10.1039/c1ob05920c

upstream raw materials:

trityl chloride

tert-butyl [(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate

D-ribo-phytosphingosine

di-tert-butyl dicarbonate

Downstream raw materials:

(4S,5S)-5-((R)-1-hydroxypentadecyl)-4-(trityloxymethyl)oxazolidin-2-one

(2S,3S,4R)-1-(((2R,6S,7R,8S,8aS)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]-dioxin-6-yl)oxy)-2-((tert-butoxycarbonyl)amino)octadecane-3,4-diyl dibenzoate

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((2S,3S,4R)-3,4-bis (benzoyloxy)-2-((tert-butoxycarbonyl)amino)octadecyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate