alpha-D-Glucopyranose, 2-bromo-2-deoxy-, 1,3,4,6-tetraacetate

Base Information

• Chemical Name: alpha-D-Glucopyranose, 2-bromo-2-deoxy-, 1,3,4,6-tetraacetate
• CAS No.: 29585-29-3
• Molecular Formula: C₁₄H₁₉BrO₉
• Molecular Weight: 411.203
• European Community (EC) Number: 608-378-4
• DSSTox Substance ID: DTXSID701197788
• Mol file: 29585-29-3.mol

Synonyms:DTXSID701197788;alpha-D-Glucopyranose, 2-bromo-2-deoxy-, 1,3,4,6-tetraacetate;29585-29-3

Chemical Property of alpha-D-Glucopyranose, 2-bromo-2-deoxy-, 1,3,4,6-tetraacetate

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 410.02124
• Heavy Atom Count: 24
• Complexity: 507

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=O)C)Br)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC(=O)C)Br)OC(=O)C)OC(=O)C

Technology Process of alpha-D-Glucopyranose, 2-bromo-2-deoxy-, 1,3,4,6-tetraacetate

There total 2 articles about alpha-D-Glucopyranose, 2-bromo-2-deoxy-, 1,3,4,6-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: 22.0%

β-D-glucose pentaacetate (604-69-3) → 1,3,4,6-tetra-O-acetyl-2-bromo-2-deoxy-α-D-glucopyranose (29585-29-3) + 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Guidance literature:

With bromine; In 2,2,4-trimethylpentane; dichloromethane; at 20 ℃; for 7h; Irradiation; Green chemistry;

DOI:10.1016/j.tetlet.2013.10.088

Reference yield:

β-D-glucose pentaacetate (604-69-3) → 1,3,4,6-tetra-O-acetyl-2-bromo-2-deoxy-α-D-glucopyranose (29585-29-3) + 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose (3947-62-4) + 2,3,4,6-tetraacetylglucose (3947-62-4,10343-06-3,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,6207-76-7)

Guidance literature:

With bromine; In acetonitrile; at 20 ℃; for 24h; Irradiation; Green chemistry;

DOI:10.1016/j.tetlet.2013.10.088

upstream raw materials:

β-D-glucose pentaacetate