2,5-anhydro-1,6-di-O-benzoyl-4-O-(methyl 2,3,4-tri-O-acetyl-D-glucopyranosyl uronate)-D-mannitol

Base Information

• Chemical Name: 2,5-anhydro-1,6-di-O-benzoyl-4-O-(methyl 2,3,4-tri-O-acetyl-D-glucopyranosyl uronate)-D-mannitol
• CAS No.: 735326-72-4
• Molecular Formula: C₃₃H₃₆O₁₆
• Molecular Weight: 688.639
• Mol file: 735326-72-4.mol

Synonyms:2,5-anhydro-1,6-di-O-benzoyl-4-O-(methyl 2,3,4-tri-O-acetyl-D-glucopyranosyl uronate)-D-mannitol

Chemical Property of 2,5-anhydro-1,6-di-O-benzoyl-4-O-(methyl 2,3,4-tri-O-acetyl-D-glucopyranosyl uronate)-D-mannitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-anhydro-1,6-di-O-benzoyl-4-O-(methyl 2,3,4-tri-O-acetyl-D-glucopyranosyl uronate)-D-mannitol

There total 2 articles about 2,5-anhydro-1,6-di-O-benzoyl-4-O-(methyl 2,3,4-tri-O-acetyl-D-glucopyranosyl uronate)-D-mannitol 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: 36.0%

2,5-anhydro-1,6-di-O-benzoyl-D-mannitol + methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8) → 3-O-acetyl-1,6-dibenzoyl-2,5-anhydro-D-mannitol + 2,5-anhydro-1,6-di-O-benzoyl-4-O-(methyl 2,3,4-tri-O-acetyl-D-glucopyranosyl uronate)-D-mannitol (735326-72-4)

Guidance literature:

2,5-anhydro-1,6-di-O-benzoyl-D-mannitol; methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate; In dichloromethane; at 20 ℃; for 2h;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 ℃;

Reference yield: 36.0%

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8) + (2R,3S,4S,5R)-3,4-dihydroxy(tetrahydrofuran-2,5-diyl)bis(methylene) dibenzoate (86363-73-7) → 3-O-acetyl-1,6-dibenzoyl-2,5-anhydro-D-mannitol + 2,5-anhydro-1,6-di-O-benzoyl-4-O-(methyl 2,3,4-tri-O-acetyl-D-glucopyranosyl uronate)-D-mannitol (735326-72-4) + methyl 3,4-di-O-acetyl-1,2-(S)-O-[1'-O-(3-O-acetyl-2,5-anhydro-1,6-di-O-benzoyl-D-mannito-4-yl)-ethylidene]-α-D-glucopyranouronate

Guidance literature:

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate; (2R,3S,4S,5R)-3,4-dihydroxy(tetrahydrofuran-2,5-diyl)bis(methylene) dibenzoate; In dichloromethane; for 2h;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 ℃; for 0.0833333h;

DOI:10.1016/j.carres.2004.03.006

Reference yield: 52.0%

benzoyl chloride (98-88-4) + 2,5-anhydro-1,6-di-O-benzoyl-4-O-(methyl 2,3,4-tri-O-acetyl-D-glucopyranosyl uronate)-D-mannitol (735326-72-4) → 2,5-anhydro-1,3,6-tri-O-benzoyl-4-O-(methyl 2,3,4-tri-O-acetyl-D-glucopyranosyl uronate)-D-mannitol

Guidance literature:

In pyridine; at 0 - 20 ℃;

DOI:10.1016/j.carres.2004.03.006

upstream raw materials:

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate

(2R,3S,4S,5R)-3,4-dihydroxy(tetrahydrofuran-2,5-diyl)bis(methylene) dibenzoate