3-O-Benzoyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose

Base Information

• Chemical Name: 3-O-Benzoyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose
• CAS No.: 13964-22-2
• Molecular Formula: C₁₉H₂₄O₇
• Molecular Weight: 364.395
• DSSTox Substance ID: DTXSID701030794
• Nikkaji Number: J416.537C
• Mol file: 13964-22-2.mol

Synonyms:DTXSID701030794;3-O-Benzoyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose;13964-22-2

Chemical Property of 3-O-Benzoyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 364.15220310
• Heavy Atom Count: 26
• Complexity: 540

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)OC(=O)C4=CC=CC=C4)C
• Isomeric SMILES: CC1(OC[C@@H](O1)[C@@H]2[C@@H]([C@@H]3[C@H](O2)OC(O3)(C)C)OC(=O)C4=CC=CC=C4)C

Technology Process of 3-O-Benzoyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose

There total 13 articles about 3-O-Benzoyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose 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: 98.0%

benzoyl chloride (98-88-4) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (13964-22-2)

Guidance literature:

With aluminum oxide; In acetonitrile; at 20 ℃; for 0.75h;

DOI:10.1016/j.carres.2005.11.035

Reference yield: 96.0%

benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (13964-22-2)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In N,N-dimethyl-formamide; at 160 ℃; for 0.25h; microwave irradiation;

DOI:10.1016/S0040-4020(98)00834-5

Reference yield: 96.0%

(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-(2-phenyl-benzo[1,3]dithiol-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxole (130132-25-1) → 3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (13964-22-2)

Guidance literature:

With tetrafluoroboric acid; mercury(II) oxide;

DOI:10.1016/S0040-4039(00)89023-1

upstream raw materials:

benzoyl chloride

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose potassium salt

(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-(2-phenyl-benzo[1,3]dithiol-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxole

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

Downstream raw materials:

6-O-benzoyl-1,2-O-isopropylidene-α-D-glucofuranose

1,2-O-isopropylidene-α-D-glucofuranose 3-O-benzoate

Benzoic acid (2R,3S,4R,5S)-4-acetoxy-2-((R)-1,2-diacetoxy-ethyl)-5-fluoro-tetrahydro-furan-3-yl ester

Benzoic acid (2R,3S,4R,5R)-4-acetoxy-2-((R)-1,2-diacetoxy-ethyl)-5-fluoro-tetrahydro-furan-3-yl ester