ethyl (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-glucopyranoside
• CAS No.: 889129-10-6
• Molecular Formula: C₃₁H₄₀O₁₄S
• Molecular Weight: 668.716

Synonyms:ethyl (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-glucopyranoside

Chemical Property of ethyl (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-glucopyranoside

There total 3 articles about ethyl (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-glucopyranoside 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: 94.0%

ethyl (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (889129-09-3) + levulinic anhydride (40608-06-8) → ethyl (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-glucopyranoside (889129-10-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 5h;

DOI:10.1002/ejoc.200500816

Reference yield:

2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate (197144-02-8,869848-87-3) → ethyl (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-glucopyranoside (889129-10-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / -75 - -55 °C

2: 94 percent / triethylamine; DMAP / CH₂Cl₂ / 5 h

With dmap; trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane;

DOI:10.1002/ejoc.200500816

Reference yield:

ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside (20701-61-5,56119-28-9,131564-36-8,142924-31-0,151123-92-1,141899-53-8) → ethyl (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-glucopyranoside (889129-10-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / -75 - -55 °C

2: 94 percent / triethylamine; DMAP / CH₂Cl₂ / 5 h

With dmap; trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane;

DOI:10.1002/ejoc.200500816

upstream raw materials:

ethyl (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

levulinic anhydride

2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate

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

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