N-BOC-ERYTHRO-SPHINGOSINE

Base Information

• Chemical Name: N-BOC-ERYTHRO-SPHINGOSINE
• CAS No.: 609812-03-5
• Molecular Formula: C₂₃H₄₅NO₄
• Molecular Weight: 399.615
• Mol file: 609812-03-5.mol

Synonyms:N-Boc-erythro-sphingosine;

Chemical Property of N-BOC-ERYTHRO-SPHINGOSINE

Chemical Property:

• Vapor Pressure: 9.42E-14mmHg at 25°C
• Melting Point: 59-60°C
• PSA: 82.28000
• LogP: 5.69460
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly), Dichloromethane (Slightly), Ethyl Acetate (Slightly), Me

Purity/Quality:

97% ^*data from raw suppliers

N-Boc-erythro-sphingosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: The N-Boc protected Sphingosine, a selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets; does not inhibit protein kinase A or myosin light chain kinase; inhibits calmodulin-dependent enzymes

Technology Process of N-BOC-ERYTHRO-SPHINGOSINE

There total 32 articles about N-BOC-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: 91.0%

tert-butyl (2R,3S,E)-2-(tert-butyldimethylsiloxy)-1-hydroxyoctadec-4-en-2-ylcarbamate (898232-47-8) → tert-butyl (3E,1R,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-carbamate (609812-03-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo060465t

Reference yield: 60.0%

tert-butyl (1R,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecynyl]-carbamate (928302-10-7) → tert-butyl (3E,1R,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-carbamate (609812-03-5)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; toluene; at 20 ℃; for 24h;

DOI:10.1016/j.chemphyslip.2006.03.001

Reference yield: 60.0%

2-(tert-butoxycarbonylamino)-2-{(4R,5S)-2,2-dimethyl-5-[(E)-1-(4-methylphenylsulfonyl)tetradecyl]-1,3-dioxolan-4-yl}-1-ethanol (609812-02-4) → tert-butyl (3E,1R,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-carbamate (609812-03-5)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In methanol; at -20 - 20 ℃; for 1.5h;

DOI:10.1021/jo034157w

upstream raw materials:

tert-butyl (1R,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecynyl]-carbamate

di-tert-butyl dicarbonate

(2R,3S,4E)-2-aminooctadec-4-ene-1,3-diol

2-(tert-butoxycarbonylamino)-2-{(4R,5S)-2,2-dimethyl-5-[(E)-1-(4-methylphenylsulfonyl)tetradecyl]-1,3-dioxolan-4-yl}-1-ethanol

Downstream raw materials:

(2S,3R,E)-1-(tert-butyldiphenylsilyloxy)-2-(N-tertbutyloxycarbonyl)aminooctadec-4-en-3-ol

Refernces

• 1、 Sanllehí, Pol,Abad, José-Luís,Bujons, Jordi,Casas, Josefina,Delgado, Antonio. "Studies on the inhibition of sphingosine-1-phosphate lyase by stabilized reaction intermediates and stereodefined azido phosphates". . p. 905 - 915. Retrieved 2016/08/24.
• 2、 Merino, Pedro,Jimenez, Pablo,Tejero, Tomas. "Enantiodivergent synthesis of D- and L-erythro-sphingosines through Mannich-type reactions of N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone". . p. 4685 - 4688. Retrieved 2007/10/03.