(2S,3R,4E)-2-TERT-BUTYLOXYCARBONYLAMINO-1-TRIPHENYLMETHYLOXY-4-OCTADECEN-2-OL

Base Information

• Chemical Name: (2S,3R,4E)-2-TERT-BUTYLOXYCARBONYLAMINO-1-TRIPHENYLMETHYLOXY-4-OCTADECEN-2-OL
• CAS No.: 299172-62-6
• Molecular Formula: C42H59NO4
• Molecular Weight: 641.935
• Mol file: 299172-62-6.mol

Synonyms:(2S,3R,4E)-2-TERT-BUTYLOXYCARBONYLAMINO-1-TRIPHENYLMETHYLOXY-4-OCTADECEN-2-OL;[(1S,2R,3E)-2-Hydroxy-1-[(triphenylMethoxy)Methyl]-3-heptadecenyl]carbaMic Acid 1,1-DiMethylethyl Ester

Chemical Property of (2S,3R,4E)-2-TERT-BUTYLOXYCARBONYLAMINO-1-TRIPHENYLMETHYLOXY-4-OCTADECEN-2-OL

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 737°C at 760 mmHg
• Flash Point: 399.523°C
• PSA: 67.79000
• Density: 1.03g/cm³
• LogP: 10.89750
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

95% ^*data from raw suppliers

(2S,3R,4E)-2-tert-Butyloxycarbonylamino-1-triphenylmethyloxy-4-octadecen-2-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,3R,4E)-2-TERT-BUTYLOXYCARBONYLAMINO-1-TRIPHENYLMETHYLOXY-4-OCTADECEN-2-OL

There total 13 articles about (2S,3R,4E)-2-TERT-BUTYLOXYCARBONYLAMINO-1-TRIPHENYLMETHYLOXY-4-OCTADECEN-2-OL 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: 77.0%

trityl chloride (76-83-5) + N-tert-butyloxycarbonylsphingosine (116467-63-1) → (+)-tert-butyl {(1S,2R,3E)-2-Hydroxy-1-[(trityloxy)methyl]heptadec-3-en-1-yl}carbamate (299172-62-6)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 - 75 ℃; for 26.5h;

DOI:10.1039/b002104k

Reference yield: 33.0%

(+)-(4E)-6-O-acetyl-2-[(tert-butoxycarbonyl)amino]-2,4,5-trideoxy-1-O-trityl-D-erythrohex-4-enitol + laurylmagnesium bromide (15890-72-9) → (+)-tert-butyl {(1S,2R,3E)-2-Hydroxy-1-[(trityloxy)methyl]heptadec-3-en-1-yl}carbamate (299172-62-6)

Guidance literature:

laurylmagnesium bromide; With copper(I) bromide dimethylsulfide complex; In diethyl ether; at -20 ℃; for 1h; Inert atmosphere;

(+)-(4E)-6-O-acetyl-2-[(tert-butoxycarbonyl)amino]-2,4,5-trideoxy-1-O-trityl-D-erythrohex-4-enitol; In diethyl ether; at -20 ℃; for 4h; Inert atmosphere;

DOI:10.1002/ejoc.201300445

Reference yield:

C30H31NO5 → (+)-tert-butyl {(1S,2R,3E)-2-Hydroxy-1-[(trityloxy)methyl]heptadec-3-en-1-yl}carbamate (299172-62-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / Reflux

2.1: 1-methyl-1H-imidazole; iodine / dichloromethane / 0 - 20 °C

3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / dichloromethane; water; methanol / 1 h / -10 - -2 °C

4.1: dmap; pyridine / dichloromethane / 1 h / 0 - 20 °C

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 12 h / 60 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

7.1: copper(I) bromide dimethylsulfide complex / diethyl ether / 1 h / -20 °C / Inert atmosphere

7.2: 4 h / -20 °C / Inert atmosphere

With pyridine; 1-methyl-1H-imidazole; dmap; 1,1'-bis-(diphenylphosphino)ferrocene; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(I) bromide dimethylsulfide complex; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201300445

upstream raw materials:

trityl chloride

N-tert-butyloxycarbonylsphingosine

laurylmagnesium bromide

Downstream raw materials:

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

3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-stearoyl-D-erythro-sphingosine

[glucose-U-(13)C]-3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-trifluoroacetyl-D-erythro-sphingosine

[glucose-(13)C6]-1-O-(β-D-glucopyranosyl)-D-erythro-sphingosine

Refernces

• 1、 Duffin, Gordon R.,Ellames, George J.,Hartmann, Sascha,Herbert, John M.,Smith, David I.. "Practical syntheses of [13C]- and [14C]-labelled glucosphingolipids". . p. 2237 - 2242. Retrieved 2007/10/03.