DL-THREO-DIHYDROSPHINGOSINE

Base Information

• Chemical Name: DL-THREO-DIHYDROSPHINGOSINE
• CAS No.: 2304-75-8
• Molecular Formula: C₁₈H₃₉NO₂
• Molecular Weight: 301.513
• Mol file: 2304-75-8.mol

Synonyms:1,3-Octadecanediol,2-amino-, (R*,R*)-(?à)-; 1,3-Octadecanediol, 2-amino-, DL-threo- (8CI); 1,3-Octadecanediol,2-amino-, (R*,R*)-; 1,3-Octadecanediol, 2-amino-, (?à)-threo-; DL-threo-Dihydrosphingosine;threo-C18-Sphinganine; threo-Sphinganine

Chemical Property of DL-THREO-DIHYDROSPHINGOSINE

Chemical Property:

• Melting Point: 107-109 °C(Solv: chloroform (67-66-3))
• Boiling Point: 446.2±25.0 °C(Predicted)
• PKA: 12.57±0.45(Predicted)
• PSA: 66.48000
• Density: 0.927±0.06 g/cm3(Predicted)
• LogP: 4.84850
• Storage Temp.: −20°C

Purity/Quality:

99%min ^*data from raw suppliers

DL-threo-Dihydrosphingosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: DL-threo-Dihydrosphingosine is a potent inhibitor of sphingosine kinase activity.

Technology Process of DL-THREO-DIHYDROSPHINGOSINE

There total 77 articles about DL-THREO-DIHYDROSPHINGOSINE 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: 100.0%

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) → (2S,3R)-2-amino-1,3-octadecanediol (764-22-7,2304-75-8,3102-56-5,3102-60-1,6036-76-6,6036-86-8,13552-09-5,15639-50-6,73938-69-9)

Guidance literature:

With hydrogen; 10percent Pd/C; In methanol; at 24 ℃; for 7.5h; under 760.051 Torr;

DOI:10.1021/ja994215o

Reference yield: 99.0%

dibenzyl 1-((2S,3R,E)-1-(benzyloxy)-3-hydroxyoctadec-5-en-2-yl)hydrazine-1,2-dicarboxylate (1463440-03-0) → (2S,3R)-2-amino-1,3-octadecanediol (764-22-7,2304-75-8,3102-56-5,3102-60-1,6036-76-6,6036-86-8,13552-09-5,15639-50-6,73938-69-9)

Guidance literature:

With hydrogen; acetic acid; In methanol; at 20 ℃; for 8h; under 3102.97 Torr;

DOI:10.1039/c3ra43048k

Reference yield: 98.0%

(2S,3R)-N-(tert-butoxycarbonyl)-<2-amino-1,3-dihydroxyoctadecane> (140408-14-6) → (2S,3R)-2-amino-1,3-octadecanediol (764-22-7,2304-75-8,3102-56-5,3102-60-1,6036-76-6,6036-86-8,13552-09-5,15639-50-6,73938-69-9)

Guidance literature:

With hydrogenchloride; In ethyl acetate; for 0.5h;

upstream raw materials:

dihydrosphingosine

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

N-Benzyloxycarbonyl-D-erythro-sphingosin

(+/-)-erythro-2-benzylamino-octadecane-1,3-diol

Downstream raw materials:

dihydroceramide d18:0/18:1(9Z)

N-((1S,2R)-2-hydroxy-1-hydroxymethyl-heptadecyl)-lauramide

n-hexadecylaldehyde

palmitic acid

Refernces

• 1、 Ashley, Ben,Campopiano, Dominic J.,Chamberlain, Joshua D.,Coleman, Aimiyah,D’Emilia, Rachel,Fu, Larina,Guan, Ziqiang,Hansen, Matthew E. B.,Klein, Eric A.,Mohan, Eric C.,Nguyen, Hung,Stankeviciute, Gabriele,Tang, Peijun. "Convergent evolution of bacterial ceramide synthesis". . . Retrieved 2022/01/06.
• 2、 Zhou, Yubai,Mukherjee, Munmun,Gupta, Anil K.,Wulff, William D.. "Multicomponent cis- and trans-Aziridinatons in the Syntheses of All Four Stereoisomers of Sphinganine". . p. 2230 - 2233. Retrieved 2017/05/12.