lactosyl lysosphingolipid

Base Information

• Chemical Name: lactosyl lysosphingolipid
• CAS No.: 109785-20-8
• Molecular Formula: C30H57 N O12
• Molecular Weight: 623.77308
• Nikkaji Number: J1.314.965H
• Mol file: 109785-20-8.mol

Synonyms:b-D-Glucopyranoside,(2S,3R,4E)-2-amino-3-hydroxy-4-octadecenyl 4-O-b-D-galactopyranosyl- (9CI); b-D-Glucopyranoside,2-amino-3-hydroxy-4-octadecenyl 4-O-b-D-galactopyranosyl-, [R-[R*,S*-(E)]]-

Chemical Property of lactosyl lysosphingolipid

Chemical Property:

• Vapor Pressure: 2.9E-33mmHg at 25°C
• Boiling Point: 845.8°Cat760mmHg
• Flash Point: 465.3°C
• PSA: 224.78000
• Density: 1.27g/cm³
• LogP: 0.27290
• Storage Temp.: -20°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 21
• Exact Mass: 623.38807625
• Heavy Atom Count: 43
• Complexity: 748

Purity/Quality:

98%,99%, ^*data from raw suppliers

Lactosyl-C18-sphingosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC=CC(C(COC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)O)O)O)O)O)N)O
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)O)O)N)O
• Description: Lactosylsphingosine is a bioactive sphingolipid and a form of lactosylceramide that is lacking the fatty acyl group. Lyso-lactosylceramide (1-50 μM) reduces viability of human neutrophils in a concentration-dependent manner. Unlike lactosylceramide, Lactosylsphingosine has no effect on protein synthesis and cell proliferation in cardiomyocytes. Lactosylsphingosine is a precursor in the synthesis of lyso-ganglioside GM3. [Matreya, LLC. Catalog No. 2088]
• Uses: Lactosyl(β) Sphingosine (d18:1) or D-lactosyl-β1-1′-D-erythro-sphingosine has been used as an internal standard for the quantification of psychosine?using tandem mass spectrometry. It may be used to screen lipids that rapidly and reversibly alter?transepithelial?electrical resistance (TER) or tight junction (TJ) permeability in epithelial?tissue. It may also be used as a standard to determine the extent of recovery of lyso-neutral glycosphingolipids (lyso-n-GSLs) from the Sephadex column.

Technology Process of lactosyl lysosphingolipid

There total 26 articles about lactosyl lysosphingolipid 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: 97.0%

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) + β-D-galactopyranosyl-(1->4)-α-D-glucopyranosyl fluoride (7584-85-2,7792-96-3,30048-41-0,66701-54-0,71328-30-8,103531-01-7,149342-82-5) → O-(β-D-galactopyranosyl)-(1→4)-(β-D-glucopyranosyl)-(1→1)-(2S, 3R, 4E)-2-aminooctadec-4-ene-1,3-diol (109785-20-8,17574-05-9)

Guidance literature:

With endoglycoceramidase II E₃₅₁S mutant glycosynthase; Triton X-100; In acetate buffer; at 20 ℃; pH=5.0; Enzymatic reaction;

DOI:10.1021/ja058469n

Reference yield: 93.0%

(2S,3R,4E)-β-galactopyranosyl-(1''->4')-β-glucopyranosyl-(1'<->1)-2-azido-4-octadecene-1,3-diol (109719-58-6) → O-(β-D-galactopyranosyl)-(1→4)-(β-D-glucopyranosyl)-(1→1)-(2S, 3R, 4E)-2-aminooctadec-4-ene-1,3-diol (109785-20-8,17574-05-9)

Guidance literature:

With pyridine; 1.3-propanedithiol; water; triethylamine; at 50 ℃; for 12h;

Reference yield: 92.0%

C48H81NO17 → O-(β-D-galactopyranosyl)-(1→4)-(β-D-glucopyranosyl)-(1→1)-(2S, 3R, 4E)-2-aminooctadec-4-ene-1,3-diol (109785-20-8,17574-05-9)

Guidance literature:

With methoxybenzene; trifluoroacetic acid; at 25 ℃; for 3h;

DOI:10.1021/acs.joc.1c00450

upstream raw materials:

(2S,3R,4E)-β-galactopyranosyl-(1''->4')-β-glucopyranosyl-(1'<->1)-2-azido-4-octadecene-1,3-diol

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

β-D-galactopyranosyl-(1->4)-α-D-glucopyranosyl fluoride

(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol