beta-D-Glucose-1-C-d pentaacetate

Base Information

• Chemical Name: beta-D-Glucose-1-C-d pentaacetate
• CAS No.: 73485-90-2
• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 391.336
• DSSTox Substance ID: DTXSID40481738
• Nikkaji Number: J389.620J
• Wikidata: Q82317333
• Mol file: 73485-90-2.mol

Synonyms:73485-90-2;beta-D-Glucose-1-C-d pentaacetate;DTXSID40481738;(5-phenoxy-3-pyridinyl)boronic?acid;beta -D-Glucose-1-C-d pentaacetate;beta-D-Glucose-1-C-d pentaacetate, 98 atom % D;1,2,3,4,6-Penta-O-acetyl-beta-D-(C~1~-~2~H)glucopyranose;[(2R,3R,4S,5R,6S)-3,4,5,6-tetraacetyloxy-6-deuteriooxan-2-yl]methyl acetate

Chemical Property of beta-D-Glucose-1-C-d pentaacetate

Chemical Property:

• Vapor Pressure: 9.23E-08mmHg at 25°C
• Melting Point: 131-134 °C(lit.)
• Refractive Index: 1.482
• Boiling Point: 434.8°C at 760 mmHg
• Flash Point: 188.1°C
• PSA: 140.73000
• Density: 1.31g/cm³
• LogP: -0.36740
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 391.12248826
• Heavy Atom Count: 27
• Complexity: 599

Purity/Quality:

98%Min ^*data from raw suppliers

BETA-D-GLUCOSE-1-C-D PENTAACETATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: [2H][C@@]1([C@@H]([C@H]([C@@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of beta-D-Glucose-1-C-d pentaacetate

There total 6 articles about beta-D-Glucose-1-C-d pentaacetate 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:

acetic anhydride (108-24-7) + 2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone (61259-48-1,73322-42-6) → 1,2,3,4,6-penta-O-acetyl-α-D-(1-2H)glucopyranose + <1-(2)H>-1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (73485-90-2)

Guidance literature:

2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone; With sodium borodeuteride; water-d2; In tetrahydrofuran; at 0 ℃;

acetic anhydride; In tetrahydrofuran; at 20 ℃; for 0.5h; Further stages.;

DOI:10.1021/ja011232g

Reference yield:

acetic anhydride (108-24-7) + 2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone (61259-48-1,73322-42-6) → <1-(2)H>-1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (73485-90-2)

Guidance literature:

With sodium borodeuteride; In tetrahydrofuran; water-d2; 1.) 0 deg C, 1 h, 2.) RT; overnight,;

DOI:10.1016/S0008-6215(00)90123-X

Reference yield:

D-glucose-1-d1 (67831-24-7,106032-61-5) + acetic anhydride (108-24-7) → 1,2,3,4,6-penta-O-acetyl-α-D-(1-2H)glucopyranose + <1-(2)H>-1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (73485-90-2)

Guidance literature:

In pyridine; at 20 ℃; for 72h; Overall yield = 96 %; Overall yield = 62 mg; Cooling with ice;

DOI:10.1002/mrc.3918

upstream raw materials:

[1-2H]-β-D-glucose

acetic anhydride

α-D-glucopyranose-1-d₁

D-Glucono-1,5-lactone

Downstream raw materials:

methyl 2,3,6-tri-O-benzyl-4-O-<2,3,4,6-tetra-O-acetyl-β-D-(1-2H)galactopyranosyl>-β-D-glucopyranoside