cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside

Base Information

• Chemical Name: cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside
• CAS No.: 866325-74-8
• Molecular Formula: C₆₂H₅₂O₁₆
• Molecular Weight: 1053.09
• Mol file: 866325-74-8.mol

Synonyms:cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside

Chemical Property of cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside

There total 7 articles about cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-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: 52.0%

allyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside (866325-72-6) + phenylboronic acid (98-80-6) → cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside (866325-74-8)

Guidance literature:

With lithium acetate; copper diacetate; palladium diacetate; In N,N-dimethyl-formamide; at 100 ℃; for 1h;

DOI:10.1016/j.tetasy.2005.06.040

Reference yield:

allyl 6-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside (866325-71-5) → cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside (866325-74-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / dimethylformamide / 18 h / 20 °C

2: 0.52 g / aq. HCl / tetrahydrofuran / 12 h / 20 °C

3: 85 percent / tetramethylurea; AgOTf / CH₂Cl₂ / 12 h / 20 °C

4: 52 percent / copper(II) acetate; lithium acetate; palladium(II) acetate / dimethylformamide / 1 h / 100 °C

With pyridine; hydrogenchloride; lithium acetate; copper diacetate; silver trifluoromethanesulfonate; palladium diacetate; tetramethylurea; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2005.06.040

Reference yield:

allyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside (866325-70-4) → cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside (866325-74-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / tetramethylurea; AgOTf / CH₂Cl₂ / 12 h / 20 °C

2: 52 percent / copper(II) acetate; lithium acetate; palladium(II) acetate / dimethylformamide / 1 h / 100 °C

With lithium acetate; copper diacetate; silver trifluoromethanesulfonate; palladium diacetate; tetramethylurea; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2005.06.040

upstream raw materials:

allyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside

phenylboronic acid

allyl 6-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside

allyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside

Downstream raw materials:

cinnamyl 6-O-(α-L-arabinopyranosyl)-β-D-glucopyranoside

Refernces