2,5-Anhydro-D-mannitol Tetraacetate

Base Information

• Chemical Name: 2,5-Anhydro-D-mannitol Tetraacetate
• CAS No.: 65729-88-6
• Molecular Formula: C14H20O9
• Molecular Weight: 332.307
• DSSTox Substance ID: DTXSID10514365
• Wikidata: Q82374655
• Mol file: 65729-88-6.mol

Synonyms:65729-88-6;2,5-Anhydro-D-mannitol Tetraacetate;[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]methyl acetate;SCHEMBL11170651;DTXSID10514365;[(2R,3R,4R,5R)-3,4-Bis(acetyloxy)oxolane-2,5-diyl]bis(methylene) diacetate (non-preferred name)

Chemical Property of 2,5-Anhydro-D-mannitol Tetraacetate

Chemical Property:

• PSA: 114.43000
• LogP: -0.25660
• Solubility.: Ethyl Acetate, Methanol, Water
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 332.11073221
• Heavy Atom Count: 23
• Complexity: 431

Purity/Quality:

98%Min ^*data from raw suppliers

2,5-Anhydro-D-mannitol Tetraacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(O1)COC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C
• Uses: Protected 2,5-Anhydro-D-mannitol.

Technology Process of 2,5-Anhydro-D-mannitol Tetraacetate

There total 1 articles about 2,5-Anhydro-D-mannitol Tetraacetate 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:

acetic anhydride (108-24-7) + C36H78B8O11 → 1,3,4,6-tetra-O-acetyl-2,5-anhydro-D-glucitol (65729-88-6) + 1,3,4,6-tetra-O-acetyl-2,5-anhydro-D-glucitol (65729-86-4) + 1,2,3,4,5,6-hexa-O-acetyl-D-glucitol (7208-47-1,5346-76-9) + 1-deoxy-D-glucose tetraacetate (13137-69-4)

Guidance literature:

With ethyldiborane⁽⁶⁾; Yield given. Multistep reaction. Yields of byproduct given; 1.) 5-6 h;

Reference yield: 90.0%

1,3,4,6-tetra-O-acetyl-2,5-anhydro-D-glucitol (65729-88-6) → 2,5-anhydro-D-mannitol (41107-82-8)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃;

DOI:10.1002/1099-0690(200103)2001:5<875::AID-EJOC875>3.0.CO;2-R

Reference yield:

1,3,4,6-tetra-O-acetyl-2,5-anhydro-D-glucitol (65729-88-6) → 1,3,4,6-tetra-O-(4-hydroxybenzoyl)-2,5-anhydro-D-mannitol (219722-53-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 81 percent / MeONa / methanol / 24 h / 20 °C

2.1: oxalyl chloride; DMF / CH₂Cl₂ / 24 h / 20 °C

2.2: 85 percent / 4-dimethylaminopyridine / pyridine / 24 h / 50 °C

3.1: 100 percent / H₂ / Pd/C / methanol; ethyl acetate / 24 h / 2585.81 Torr

With oxalyl dichloride; hydrogen; sodium methylate; N,N-dimethyl-formamide; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;

DOI:10.1021/jo010423z

upstream raw materials:

acetic anhydride

Downstream raw materials:

2,5-anhydro-D-mannitol

1,3,4,6-tetra-O-(4-hydroxybenzoyl)-2,5-anhydro-D-mannitol

1,3,4,6-tetra-O-(4-benzyloxybenzoyl)-2,5-anhydro-D-mannitol

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