1,4-Anhydro-D-glucitol tetraacetate

Base Information

• Chemical Name: 1,4-Anhydro-D-glucitol tetraacetate
• CAS No.: 53905-78-5
• Molecular Formula: C14H20O9
• Molecular Weight: 332.307
• European Community (EC) Number: 258-855-2
• DSSTox Substance ID: DTXSID80968694
• Mol file: 53905-78-5.mol

Synonyms:53905-78-5;1,2,4,5-Tetra-O-acetyl-3,6-anhydrohexitol;1,4-Anhydro-D-glucitol tetraacetate;EINECS 258-855-2;DTXSID80968694;XYTVZFGQLPBQQL-UHFFFAOYSA-N;Tetra-O-acetyl-1,4-anhydro-d-glucitol;D-Glucitol, 1,4-anhydro-, tetraacetate;1,2,4,5-Tetra-O-acetyl-3,6-anhydrohexitol #

Chemical Property of 1,4-Anhydro-D-glucitol tetraacetate

Chemical Property:

• Vapor Pressure: 5.92E-07mmHg at 25°C
• Boiling Point: 410.7°Cat760mmHg
• Flash Point: 179.6°C
• Density: 1.26g/cm³
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 332.11073221
• Heavy Atom Count: 23
• Complexity: 473

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(C1C(C(CO1)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 1,4-Anhydro-D-glucitol tetraacetate

There total 9 articles about 1,4-Anhydro-D-glucitol 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: 12.0%

acetic anhydride (108-24-7) + 1,4-anhydro-D-glucitol (7726-97-8,10334-28-8,20662-31-1,22554-76-3,22554-77-4,22554-79-6,27299-12-3,28218-56-6,32742-35-1,40026-08-2,51196-40-8,51607-77-3,53648-56-9,96243-58-2,124379-08-4,124379-13-1) → [(2R)-2-acetoxy-2-[(2R,3R,4S)-3,4-diacetoxytetrahydrofuran-2-yl]ethyl] acetate (53905-78-5)

Guidance literature:

With triethylamine; In dichloromethane; at 25 ℃; for 12h; Inert atmosphere;

Reference yield:

1-Amino-1-deoxy-D-glucitol (488-43-7) → [(2R)-2-acetoxy-2-[(2R,3R,4S)-3,4-diacetoxytetrahydrofuran-2-yl]ethyl] acetate (53905-78-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium nitrite; aqueous acetic acid

2: pyridine

With pyridine; acetic acid; sodium nitrite;

DOI:10.1039/jr9480000299

Reference yield:

acetic anhydride (108-24-7) + C44H94B8O11 (83823-00-1,96532-70-6,96613-28-4) → 1,2,3,4,5,6-hexa-O-acetyl-D-glucitol (7208-47-1,5346-76-9) + Acetic acid (1R,2R,3R)-3,4-diacetoxy-1-((S)-1,2-diacetoxy-ethyl)-2-((2S,3R,4R,5R)-2,3,4,5,6-pentaacetoxy-hexyloxy)-butyl ester (96532-72-8,96614-03-8) + 1-deoxy-D-glucose tetraacetate (13137-69-4) + [(2R)-2-acetoxy-2-[(2R,3R,4S)-3,4-diacetoxytetrahydrofuran-2-yl]ethyl] acetate (53905-78-5)

Guidance literature:

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

upstream raw materials:

acetic anhydride

1,4-anhydro-D-glucitol

C₄₄H₉₄B₈O₁₁

C₄₄H₉₄B₈O₁₁