3-O-(TERT-BUTYLDIMETHYLSILYLOXY)-2-FMOC-ERYTHRO-SPHINGOSINE

Base Information

• Chemical Name: 3-O-(TERT-BUTYLDIMETHYLSILYLOXY)-2-FMOC-ERYTHRO-SPHINGOSINE
• CAS No.: 149035-77-8
• Molecular Formula: C39H61NO4Si
• Molecular Weight: 636.003
• Mol file: 149035-77-8.mol

Synonyms:3-O-(TERT-BUTYLDIMETHYLSILYLOXY)-2-FMOC-ERYTHRO-SPHINGOSINE;(2S,3R,4E)-2-AMINO-3-(TERTBUTYLDIMETHYLSILYLOXY)-2-FLUORENYLCARBONYLAMINO-4-OCTADECENE-1-OL

Chemical Property of 3-O-(TERT-BUTYLDIMETHYLSILYLOXY)-2-FMOC-ERYTHRO-SPHINGOSINE

Chemical Property:

• Vapor Pressure: 2.96E-21mmHg at 25°C
• Boiling Point: 711.6°C at 760 mmHg
• PKA: 10.83±0.46(Predicted)
• Flash Point: 384.2°C
• PSA: 67.79000
• Density: 1.012g/cm³
• LogP: 10.92460
• Solubility.: Acetone, Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

3-O-(tert-Butyldimethylsilyloxy)-2-Fmoc-erythro-sphingosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-O-(TERT-BUTYLDIMETHYLSILYLOXY)-2-FMOC-ERYTHRO-SPHINGOSINE

There total 2 articles about 3-O-(TERT-BUTYLDIMETHYLSILYLOXY)-2-FMOC-ERYTHRO-SPHINGOSINE 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: 92.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (2S,3R,4E)-2-amino-3-(tert-butyldimethylsilyloxy)-4-octadecene-1-ol (137905-29-4) → (2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(9-fluorenylmethyloxycarbonylamino)-4-octadecene-1-ol (149035-77-8)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water;

DOI:10.1016/S0040-4039(00)60772-4

Reference yield:

(2S,3S,4E)-2-azido-3-O-(tert-butyldimethylsilyl)-4-octadecen-1,3-diol (114299-64-8) → (2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(9-fluorenylmethyloxycarbonylamino)-4-octadecene-1-ol (149035-77-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Ph₃P, H₂O, pyridine

2: 92 percent / NaHCO₃ / dioxane; H₂O

With pyridine; water; sodium hydrogencarbonate; triphenylphosphine; In 1,4-dioxane; water;

DOI:10.1016/S0040-4039(00)60772-4

Reference yield:

(2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(9-fluorenylmethyloxycarbonylamino)-4-octadecene-1-ol (149035-77-8) → Sphingosine-1-phosphate (26993-30-6,26993-39-5)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrazole / CH₂Cl₂; acetonitrile / 0.5 h

2: iodine, pyridine, water / CH₂Cl₂

3: 95 percent / 33percent HNMe₂ / ethanol / 72 h / 45 °C

4: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran / 72 h / 45 °C

With pyridine; 1H-tetrazole; tetrabutyl ammonium fluoride; water; iodine; dimethyl amine; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)60772-4

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(2S,3R,4E)-2-amino-3-(tert-butyldimethylsilyloxy)-4-octadecene-1-ol

(2S,3S,4E)-2-azido-3-O-(tert-butyldimethylsilyl)-4-octadecen-1,3-diol

Downstream raw materials:

Sphingosine-1-phosphate

Refernces

• 1、 Kratzer, Bernd,Schmidt, Richard R.. "An efficient synthesis of sphingosine-1-phosphate". . p. 1761 - 1764. Retrieved 2007/10/02.