.beta.-D-arabino-Hexopyranose, 1,6-anhydro-3-deoxy-, 2-acetate

Base Information

• Chemical Name: .beta.-D-arabino-Hexopyranose, 1,6-anhydro-3-deoxy-, 2-acetate
• CAS No.: 102719-14-2
• Molecular Formula: C₈H₁₂O₅
• Molecular Weight: 188.18
• Mol file: 102719-14-2.mol

Synonyms:6,8-Dioxabicyclo[3.2.1]octane,b-D-arabino-hexopyranose deriv.

Chemical Property of .beta.-D-arabino-Hexopyranose, 1,6-anhydro-3-deoxy-, 2-acetate

Chemical Property:

• PSA: 64.99000
• LogP: -0.57580

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of .beta.-D-arabino-Hexopyranose, 1,6-anhydro-3-deoxy-, 2-acetate

There total 5 articles about .beta.-D-arabino-Hexopyranose, 1,6-anhydro-3-deoxy-, 2-acetate 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: 95.0%

2-O-acetyl-1,6-anhydro-4-O-benzyl-3-deoxy-β-D-arabino-hexopyranose (102719-12-0) → 2-O-acetyl-1,6-anhydro-3-deoxy-β-D-arabino-hexopyranose (102719-14-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 2h;

DOI:10.1016/0008-6215(86)85029-7

Reference yield:

C14H26O5Si → 2-O-acetyl-1,6-anhydro-3-deoxy-β-D-ribo-hexopyranose (102719-15-3) + 2-O-acetyl-1,6-anhydro-3-deoxy-β-D-arabino-hexopyranose (102719-14-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 22 ℃; for 5h;

DOI:10.1016/j.tet.2018.03.023

Reference yield:

levoglucosenone (37112-31-5) → 2-O-acetyl-1,6-anhydro-3-deoxy-β-D-arabino-hexopyranose (102719-14-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent / KH / 0.08 h

2: NaBH₄ / H₂O; methanol / 0.17 h

3: 100 percent / pyridine

4: 95 percent / H₂ / 10percent Pd-C / ethanol / 2 h

With sodium tetrahydroborate; hydrogen; potassium hydride; palladium on activated charcoal; In pyridine; methanol; ethanol; water;

DOI:10.1016/0008-6215(86)85029-7

upstream raw materials:

2-O-acetyl-1,6-anhydro-4-O-benzyl-3-deoxy-β-D-arabino-hexopyranose

levoglucosenone

1,6-anhydro-4-O-benzyl-3-deoxy-β-D-erythro-hexopyranos-2-ulose

1,6-anhydro-4-O-benzyl-3-deoxy-β-D-arabino-hexopyranose

Downstream raw materials:

isolevoglucosenone

Acetic acid (1R,4S,5R)-2-oxo-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

Refernces

• 1、 Furneaux, Richard H.,Gainsford, Graeme J.,Shafizadeh, Fred,Stevenson, Thomas T.. "SYNTHESIS AND THERMAL CHEMISTRY OF ISOLEVOGLUCOSENONE". . p. 113 - 128. Retrieved 2007/10/02.