beta-D-Glucose pentaacetate

Base Information

• Chemical Name: beta-D-Glucose pentaacetate
• CAS No.: 3891-59-6
• Molecular Formula: C16H22O11
• Molecular Weight: 390.344
• Hs Code.: 29400090
• European Community (EC) Number: 210-074-8
• UNII: V833P95COC
• Nikkaji Number: J14.175E
• Wikidata: Q27291653
• ChEMBL ID: CHEMBL438446
• Mol file: 3891-59-6.mol

Synonyms:1,2,3,4,6-penta-O-acetyl-alpha-D-glucopyranoside;beta-D-glucose pentaacetate;glucose pentaacetate;glucose pentaacetate, (alpha-D)-isomer;glucose pentaacetate, (beta-(D))-isomer;glucose pentaacetate, (D)-isomer;penta-O-acetyl-alpha-D-glucopyranose;penta-O-acetylglucopyranose

Chemical Property of beta-D-Glucose pentaacetate

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 109-113℃
• Refractive Index: 1.482
• Boiling Point: 434.8 °C at 760 mmHg
• Flash Point: 188.1 °C
• PSA: 148.57000
• Density: 1.3 g/cm³
• LogP: -0.52480
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Water Solubility.: < 5 G/L (25℃)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 390.11621151
• Heavy Atom Count: 27
• Complexity: 599

Purity/Quality:

99%, ^*data from raw suppliers

α-D-Glucose Pentaacetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Monosaccharides and Derivatives
• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=O)C)OC(=O)C)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)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of beta-D-Glucose pentaacetate

There total 28 articles about beta-D-Glucose 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: 92.0%

D-glucose (50-99-7) + acetic anhydride (108-24-7) → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

Guidance literature:

In 1-butyl-3-methylimidazolium methyl phosphonate; at 20 ℃; for 15h;

Reference yield: 79.0%

2,3,4,5,6-penta-O-acetyl-D-glucose diethyl dithioacetal (4984-72-9) → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

Guidance literature:

With water; mercury dichloride; mercury(II) oxide; In acetone; for 48h; Product distribution; Ambient temperature; reagent, time, temperature;

DOI:10.1016/0008-6215(84)85080-6

Reference yield: 60.0%

2,3,4,5,6-penta-O-acetyl-D-galactose diethyl dithioacetal (72003-68-0) → 2,3,4,5,6-penta-O-acetyl-aldehydo-L-galactose (3891-59-6,6763-46-8,66888-27-5,99032-29-8,101399-27-3,128990-41-0,128990-42-1,128990-43-2,129905-46-0,129905-51-7)

Guidance literature:

With periodic acid; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; for 0.333333h;

DOI:10.1016/j.tetlet.2012.12.048

upstream raw materials:

2,3,4,5,6-penta-O-acetyl-D-glucose diethyl dithioacetal

D-glucose

acetic anhydride

(Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ^1,α-acetonitrile

Downstream raw materials:

LACTIC ACID

1,2:3,4-di-O-isopropylidene-α-L-galactopyranose

aldehydo-L-Galactose

eugenyl glucoside

Refernces

• 1、 Wolfrom et al.. "-". . p. 1794. Retrieved 1934.
• 2、 Huang, Xiang-Zhong,Jiang, Meng-Yuan,Li, Yan-Hong,Lu, Huai,Pu, Xiao-Yun,Tian, Kai,Wang, Wei,Xiong, Yong. "Laxative Metabolites from the Leaves of Moringa oleifera". . p. 7850 - 7860. Retrieved 2020.
• 3、 Zhang, Zhanjun,Wang, Fuhua,Wang, Mingchun,Ma, Liping,Ye, Hong,Zeng, Xiaoxiong. "A comparative study of the neutral and acidic polysaccharides from Allium macrostemon Bunge". . p. 980 - 987. Retrieved 2015/01/09.
• 4、 Ló, Stephanie M.S.,Cunico, Juliana C.,Ducatti, Diogo R.B.,Orsato, Alexandre,Duarte, M. Eugênia R.,Barreira, Sandra M.W.,Noseda, Miguel D.,Gon?alves, Alan G.. "Synthesis of peracetylated C-1-deoxyalditol- and C-glycoside-dipyrranes via dithioacetal derivatives". supporting information. p. 1137 - 1140. Retrieved 2013/05/08.