1-O-β-D-Glucopyranosyl-N-hexadecanoylsphingosine

Base Information

• Chemical Name: 1-O-β-D-Glucopyranosyl-N-hexadecanoylsphingosine
• CAS No.: 74365-77-8
• Molecular Formula: C40H77NO8
• Molecular Weight: 700.04
• Mol file: 74365-77-8.mol

Synonyms:(2S,3R,4E)-2-(Hexadecanoylamino)-1-(β-D-glucopyranosyloxy)-4-octadecen-3-ol;1-O-β-D-Glucopyranosyl-N-hexadecanoylsphingosine;1-O-β-D-Glucopyranosyl-N-palmitoylsphingosine;C16:0-GlcCer;C16:0-GluCer;D-erythro-N-Palmitoyl-glucosyl-C18-Sphingosine;D-glucosyl--1,1' N-palMitoyl-D-erythro-sphingosine

Chemical Property of 1-O-β-D-Glucopyranosyl-N-hexadecanoylsphingosine

Chemical Property:

• PSA: 148.71000
• LogP: 7.77810

Purity/Quality:

99% ^*data from raw suppliers

D-GLUCOSYL-BETA-1,1'-N-PALMITOYL-D-ERYTHRO-SPHINGOSINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-β-D-Glucopyranosyl-N-hexadecanoylsphingosine

There total 48 articles about 1-O-β-D-Glucopyranosyl-N-hexadecanoylsphingosine 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%

Benzoic acid (E)-(R)-1-[(S)-1-hexadecanoylamino-2-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester (94069-99-5,94132-56-6,116558-60-2,124377-35-1) → glucosylceramide (74365-77-8)

Guidance literature:

With potassium hydroxide; for 5h; Ambient temperature;

DOI:10.1248/cpb.40.1154

Reference yield: 91.0%

Glucosylsphingosine (52050-17-6) + n-hexadecanoyl chloride (112-67-4) → glucosylceramide (74365-77-8)

Guidance literature:

With sodium acetate; In tetrahydrofuran; water; for 2h;

DOI:10.1016/S0009-3084(01)00152-9

Reference yield: 86.4%

(2S,3R,4E)-2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol (183901-68-0) → glucosylceramide (74365-77-8)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; at 20 ℃; for 12h; pH=9;

DOI:10.1080/07328300600859825

upstream raw materials:

Benzoic acid (E)-(R)-1-[(S)-1-hexadecanoylamino-2-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester

Glucosylsphingosine

n-hexadecanoyl chloride

(2S,3R,4E)-2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol

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