3β-O-(3-O-benzyl-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranosyl)cholesterol

Base Information

• Chemical Name: 3β-O-(3-O-benzyl-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranosyl)cholesterol
• CAS No.: 889129-03-7
• Molecular Formula: C₅₂H₇₂O₈
• Molecular Weight: 825.139

Synonyms:3β-O-(3-O-benzyl-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranosyl)cholesterol

Chemical Property of 3β-O-(3-O-benzyl-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranosyl)cholesterol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 3β-O-(3-O-benzyl-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranosyl)cholesterol

There total 3 articles about 3β-O-(3-O-benzyl-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranosyl)cholesterol 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: 68.0%

(2R,4aR,6S,7R,8S,8aR)-8-(benzyloxy)-6-(ethylthio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl 4-oxopentanoate (889129-00-4) + cholesterol (57-88-5) → 3β-O-(3-O-benzyl-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranosyl)cholesterol (889129-03-7)

Guidance literature:

With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane;

DOI:10.1002/ejoc.200500816

Reference yield:

levulinic acid (123-76-2) → 3β-O-(3-O-benzyl-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranosyl)cholesterol (889129-03-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / N,N-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂

2: 68 percent / dimethyl(methylthio)sulfonium trifluoromethanesulfonate / CH₂Cl₂

With dmap; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1002/ejoc.200500816

Reference yield:

ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (141810-60-8) → 3β-O-(3-O-benzyl-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranosyl)cholesterol (889129-03-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / N,N-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂

2: 68 percent / dimethyl(methylthio)sulfonium trifluoromethanesulfonate / CH₂Cl₂

With dmap; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1002/ejoc.200500816

upstream raw materials:

(2R,4aR,6S,7R,8S,8aR)-8-(benzyloxy)-6-(ethylthio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl 4-oxopentanoate

cholesterol

levulinic acid

ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Downstream raw materials:

3β-O-{(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-[(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)]-4,6-O-benzylidene-β-D-glucopyranosyl}cholesterol

3β-O-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl]cholesterol

3β-O-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-4,6-O-benzylidene-β-D-glucopyranosyl]cholesterol

3'β-O-(3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)cholesterol

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