2-o-Acetyl-1,4:3,6-dianhydrohexitol

Base Information

• Chemical Name: 2-o-Acetyl-1,4:3,6-dianhydrohexitol
• CAS No.: 13042-39-2
• Molecular Formula: C8H12O5
• Molecular Weight: 188.18
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID80926734
• Nikkaji Number: J270.206A
• Mol file: 13042-39-2.mol

Synonyms:2-o-acetyl-1,4:3,6-dianhydrohexitol;EINECS 235-917-7;(3S,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl acetate;SCHEMBL10194441;DTXSID80926734;FT-0654146;A806086;(3S,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl acetate*

Chemical Property of 2-o-Acetyl-1,4:3,6-dianhydrohexitol

Chemical Property:

• Vapor Pressure: 2.13E-05mmHg at 25°C
• Melting Point: 78 °C
• Refractive Index: 1.51
• Boiling Point: 322.976 °C at 760 mmHg
• PKA: 13.35±0.40(Predicted)
• Flash Point: 132.52 °C
• PSA: 64.99000
• Density: 1.348 g/cm³
• LogP: -0.92340
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 188.06847348
• Heavy Atom Count: 13
• Complexity: 217

Purity/Quality:

99% ^*data from raw suppliers

1,4:3,6-Dianhydro-2-O-acetyl-D-glucitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1COC2C1OCC2O
• Uses: 1,4:3,6-Dianhydro-2-O-acetyl-D-glucitol is a useful reagent in the practical enzymic synthesis of isosorbide-2-acetate.

Technology Process of 2-o-Acetyl-1,4:3,6-dianhydrohexitol

There total 21 articles about 2-o-Acetyl-1,4:3,6-dianhydrohexitol 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: 91.3%

[(3S,3aR,6R,6aR)-6-acetoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] acetate (13042-38-1,54522-25-7) → isosorbide 2-acetate (13042-39-2)

Guidance literature:

In acetone; for 288h; Ambient temperature; lipase from Pseudomonas sp. (SAM II);

DOI:10.1016/S0957-4166(00)82092-3

Reference yield: 91.0%

n-heptan1ol (111-70-6) + [(3S,3aR,6R,6aR)-6-acetoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] acetate (13042-38-1,54522-25-7) → isosorbide 2-acetate (13042-39-2)

Guidance literature:

In acetone;

Reference yield: 90.0%

acetic anhydride (108-24-7) + Isosorbide (652-67-5) → isosorbide 2-acetate (13042-39-2) + (6S,3R,3aR,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl acetate (65940-93-4) + [(3S,3aR,6R,6aR)-6-acetoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] acetate (13042-38-1,54522-25-7)

Guidance literature:

at 120 - 140 ℃; for 1h; Yields of byproduct given;

DOI:10.1055/s-1987-27878

upstream raw materials:

D-sorbitol

ethyl acetate

acetic anhydride

Isosorbide

Downstream raw materials:

isosorbide mononitrate

(1R,4S,5R,8R)-8-benzyloxy-4-toluenesulfonyloxy-2,6-dioxabicyclo<3.3.0>octane

(1R,4S,5R,8R)-8-benzyloxy-2,6-dioxabicyclo<3.3.0>octan-4-ol

(3R,3aS,6S,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

Refernces

• 1、 -. "Method for synthesizing isohexitol ester". Paragraph 0010; 0043-0050; 0055-0056. . Retrieved 2021/05/05.
• 2、 Zhu, Shi-Guo,Huang, Jia-Xin,Zhang, Gui-Min,Chen, Shao-Xin,Zhang, Fu-Li. "Development of a Practical Enzymatic Synthesis of Isosorbide-2-acetate". . p. 1548 - 1552. Retrieved 2018/11/25.