2,3,4-Tri-O-acetyl-1,6-anhydromannopyranose

Base Information

• Chemical Name: 2,3,4-Tri-O-acetyl-1,6-anhydromannopyranose
• CAS No.: 13242-48-3
• Molecular Formula: C12H16 O8
• Molecular Weight: 288.254
• Hs Code.: 2932999099
• Mol file: 13242-48-3.mol

Synonyms:2,3,4-tri-O-acetyl-1,6-anhydro-D-mannopyranose;2,3,4-tri-O-acetyl-1,6-anhydromannopyranose;2,3,4-triAc-AHMan

Chemical Property of 2,3,4-Tri-O-acetyl-1,6-anhydromannopyranose

Chemical Property:

• Vapor Pressure: 2.37E-06mmHg at 25°C
• Boiling Point: 392°Cat760mmHg
• Flash Point: 147.4°C
• PSA: 97.36000
• Density: 1.34g/cm³
• LogP: -0.46340
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 288.08451746
• Heavy Atom Count: 20
• Complexity: 420

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C2COC(O2)C(C1OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)O[C@@H]1[C@@H]2CO[C@@H](O2)[C@H]([C@H]1OC(=O)C)OC(=O)C

Technology Process of 2,3,4-Tri-O-acetyl-1,6-anhydromannopyranose

There total 10 articles about 2,3,4-Tri-O-acetyl-1,6-anhydromannopyranose 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: 64.0%

acetic anhydride (108-24-7) + 1,2,3,4-tetra-O-acetyl-6-O-deoxy-6-tosyl-α/β-D-mannopyranose (78478-66-7) → 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-mannopyranose (13242-48-3,33360-71-3)

Guidance literature:

1,2,3,4-tetra-O-acetyl-6-O-deoxy-6-tosyl-α/β-D-mannopyranose; With aluminum oxide; at 110 ℃; for 0.116667h; microwave irradiation;

acetic anhydride; With potassium acetate; at 100 ℃; for 0.333333h;

DOI:10.1055/s-2003-39168

Reference yield: 58.0%

2,3,4-Tri-O-acetyl-6-O-(p-tolylsulfonyl)-α/β-D-mannopyranose (121363-55-1,121363-56-2,121363-62-0,121363-63-1,121363-67-5,121363-68-6) → 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-mannopyranose (13242-48-3,33360-71-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; Ambient temperature;

DOI:10.1055/s-1989-27192

Reference yield:

acetic anhydride (108-24-7) + 1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose (139437-39-1) → 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-mannopyranose (13242-48-3,33360-71-3) + 2,3,4-tri-O-acetyllevoglucosan (13242-55-2,33360-71-3)

Guidance literature:

With pyridine; air; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) toluene, 60 deg C, 3 h;

DOI:10.1016/0040-4039(94)88272-X

upstream raw materials:

acetic anhydride

mannosan

phenyl β-D-mannopyranoside

dianhydroaltrose

Downstream raw materials:

mannosan

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

Refernces

• 1、 Ionescu, C?t?lina,Huseynova, Fidan,Barragan-Montero, Véronique. "Pathways in the synthesis of functionalized glycolipids for liposomal preparations". . . Retrieved 2021/12/01.
• 2、 Madsen, Robert,Udodong, Uko E.,Roberts, Carmichad,Mootoo, David R.,Konradsson, Peter,Fraser-Reid, Bert. "Studies related to synthesis of glycophosphatidylinositol membrane-bound protein anchors. 6. Convergent assembly of subunits". . p. 1554 - 1565. Retrieved 2007/10/02.