ethyl 7-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3,5,8,9,10-pentamethoxy-1-methylanthracene-2-carboxylate

Base Information

• Chemical Name: ethyl 7-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3,5,8,9,10-pentamethoxy-1-methylanthracene-2-carboxylate
• CAS No.: 137410-35-6
• Molecular Formula: C₅₇H₆₀O₁₂
• Molecular Weight: 937.096

Synonyms:ethyl 7-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3,5,8,9,10-pentamethoxy-1-methylanthracene-2-carboxylate

Chemical Property of ethyl 7-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3,5,8,9,10-pentamethoxy-1-methylanthracene-2-carboxylate

Chemical Property:

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Technology Process of ethyl 7-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3,5,8,9,10-pentamethoxy-1-methylanthracene-2-carboxylate

There total 3 articles about ethyl 7-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3,5,8,9,10-pentamethoxy-1-methylanthracene-2-carboxylate 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: 40.0%

2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl trifluoroacetate (129889-18-5) + ethyl 1-methyl-3,5,8,9,10-pentamethoxyl-2-anthracene carboxylate (137410-34-5) → ethyl 7-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3,5,8,9,10-pentamethoxy-1-methylanthracene-2-carboxylate (137410-35-6)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile;

DOI:10.1039/c39910001319

Reference yield:

3,5,8-Trimethoxy-1-methyl-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid ethyl ester (137410-33-4) → ethyl 7-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3,5,8,9,10-pentamethoxy-1-methylanthracene-2-carboxylate (137410-35-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) aq. sodium dithionite, Bu₄NBr, KOH / 1.) THF, 15 min; 10 min, 2.) 0 deg C, 2 h; 0 deg C to r.t.

2: BF₃*Et₂O / acetonitrile / 0.5 h

With potassium hydroxide; sodium dithionite; boron trifluoride diethyl etherate; tetrabutylammomium bromide; In acetonitrile;

DOI:10.1039/a705145j

Reference yield:

ethyl 1-methyl-3,5,8,9,10-pentamethoxyl-2-anthracene carboxylate (137410-34-5) + 2,3,4,6-tetra-O-benzyl-1-O-(trifluoroacetyl)-α-D-glucopyranose (125343-69-3) → ethyl 7-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3,5,8,9,10-pentamethoxy-1-methylanthracene-2-carboxylate (137410-35-6)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; for 0.5h; Yield given;

DOI:10.1039/a705145j

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl trifluoroacetate

ethyl 1-methyl-3,5,8,9,10-pentamethoxyl-2-anthracene carboxylate

2,3,4,6-tetra-O-benzyl-1-O-(trifluoroacetyl)-α-D-glucopyranose

3,5,8-Trimethoxy-1-methyl-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid ethyl ester

Downstream raw materials:

3,5,8-Trimethoxy-1-methyl-9,10-dioxo-7-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-9,10-dihydro-anthracene-2-carboxylic acid ethyl ester

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