3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside

Base Information

• Chemical Name: 3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside
• CAS No.: 1521271-26-0
• Molecular Formula: C₄₂H₃₁F₂NO₁₀
• Molecular Weight: 747.706
• Mol file: 1521271-26-0.mol

Synonyms:3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside

Chemical Property of 3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside

There total 2 articles about 3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzoyl-α-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: 75.0%

2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2) + 3,3-difluoro-1,3-dihydro-2H-indol-2-one (197067-27-9) → 3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside (1521271-26-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; silver(l) oxide; In dichloromethane; at 20 ℃; for 10h; Molecular sieve; Inert atmosphere;

DOI:10.1021/ja411746a

Reference yield:

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → 3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside (1521271-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1: diethylamino-sulfur trifluoride / Inert atmosphere

2: silver(l) oxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 20 °C / Molecular sieve; Inert atmosphere

With diethylamino-sulfur trifluoride; N-ethyl-N,N-diisopropylamine; silver(l) oxide; In dichloromethane;

DOI:10.1021/ja411746a

Reference yield: 94.0%

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + 3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside (1521271-26-0) → methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl)-α-D-glucopyranoside (128503-39-9,143995-74-8,125084-78-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 0.0833333h; Molecular sieve; Inert atmosphere;

DOI:10.1021/ja411746a

upstream raw materials:

2,3,4,6-tetra-O-benzoylglucosyl bromide

3,3-difluoro-1,3-dihydro-2H-indol-2-one

indole-2,3-dione

Downstream raw materials:

1,2:3:4-di-O-isopropylidene-6-O-(tetra-O-benzoyl-β-D-glucopyranosyl)-α-D-galactose

methyl 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl)-α-D-glucopyranoside