Cerebroside B

Base Information

• Chemical Name: Cerebroside B
• CAS No.: 88642-46-0
• Molecular Weight: 728.05
• ChEMBL ID: CHEMBL538217
• DSSTox Substance ID: DTXSID201104435
• Metabolomics Workbench ID: 156346
• Nikkaji Number: J152.372D
• Wikidata: Q105346034

Synonyms:cerebroside B

Chemical Property of Cerebroside B

Chemical Property:

• XLogP3: 10.2
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 32
• Exact Mass: 727.55983303
• Heavy Atom Count: 51
• Complexity: 900

Purity/Quality:

98%Min ^*data from raw suppliers

CerebrosideB 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCC(C(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C=CCCC=C(C)CCCCCCCCC)O)O
• Isomeric SMILES: CCCCCCCCCCCCCC[C@H](C(=O)N[C@@H](CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)[C@@H](/C=C/CC/C=C(\C)/CCCCCCCCC)O)O

Technology Process of Cerebroside B

There total 21 articles about Cerebroside B 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: 90.0%

1-O-(2'',3'',4'',6''-tetra-O-benzoyl-β-D-glucopyranosyl)-(2S,3R,4E,8E)-2-[(2'R)-2'-((benzoyloxy)hexadecanoyl)amino]-3-O-benzoyl-9-methyl-4,8-octadecadiene-1,3-diol (1220969-59-4) → 1-O-(β-D-glucopyranosyl)-(2S,3R,4E,8E)-2-[(2'R)-2'-(hydroxyhexadecanoyl)amido]-9-methyl-4,8-octadecadiene-1,3-diol (88642-46-0,106037-29-0)

Guidance literature:

With methanol; sodium methylate; In tetrahydrofuran; at 0 - 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1039/b920285d

Reference yield: 86.0%

(2S,3R,4E,8E,2'R)-2-(2'-acetoxyhexadecanoyl)amino-3-O-benzoyl-1-O-(2'',3'',4'',6''-tetra-O-benzoyl-β-D-glucopyranosyl)-9-methyl-4,8-octadecadiene-1,3-diol → 1-O-(β-D-glucopyranosyl)-(2S,3R,4E,8E)-2-[(2'R)-2'-(hydroxyhexadecanoyl)amido]-9-methyl-4,8-octadecadiene-1,3-diol (88642-46-0,106037-29-0)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; at 5 - 10 ℃; for 2h;

DOI:10.1016/j.tet.2005.07.066

Reference yield: 71.4%

(4E,8E,2S,3R,2'R)-N-2'-hydroxyhexadecanoyl-1-O-β-D-glucopyranosyl-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine (100924-07-0) → 1-O-(β-D-glucopyranosyl)-(2S,3R,4E,8E)-2-[(2'R)-2'-(hydroxyhexadecanoyl)amido]-9-methyl-4,8-octadecadiene-1,3-diol (88642-46-0,106037-29-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 20h; Ambient temperature;

DOI:10.1016/S0040-4020(01)96633-5

upstream raw materials:

(4E,8E,2S,3R,2'R)-N-2'-hydroxyhexadecanoyl-1-O-β-D-glucopyranosyl-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine

(R)-(-)-2-hydroxyhexadecanoic acid

methyl (R)-2-hydroxyhexadecanoate

D(R)-α-acetoxypalmitic acid

Downstream raw materials:

(R)-(-)-2-hydroxyhexadecanoic acid

methyl (R)-2-hydroxyhexadecanoate

(R)-2-((R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-hexadecanoic acid methyl ester

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