(2S,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

Base Information

• Chemical Name: (2S,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
• CAS No.: 492-62-6
• Deprecated CAS: 26655-34-5,95671-82-2
• Molecular Formula: C6H12O6
• Molecular Weight: 180.158
• Hs Code.: 1702.30
• European Community (EC) Number: 207-757-8,607-980-4
• UNII: 5J5I9EB41E
• DSSTox Substance ID: DTXSID30197710
• Nikkaji Number: J44.217H
• Wikidata: Q23905965
• NCI Thesaurus Code: C77427
• Metabolomics Workbench ID: 73628
• ChEMBL ID: CHEMBL423707
• Mol file: 492-62-6.mol

Synonyms:1,3-alpha-D-glucan;alpha-1,3-glucan

Chemical Property of (2S,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

Chemical Property:

• Appearance/Colour: white, odorless, fine crystalline powder odurless
• Melting Point: 153-156 °C(lit.)
• Refractive Index: n20/D 1.362
• Boiling Point: 410.797 °C at 760 mmHg
• PKA: 12.12±0.70(Predicted)
• Flash Point: 202.243 °C
• PSA: 110.38000
• Density: 1.732 g/cm³
• LogP: -3.22140
• Storage Temp.: 2-8°C
• Solubility.: H2O: 1 M at 20 °C, clear, colorless
• Water Solubility.: 450.5g/L(25 oC)
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 180.06338810
• Heavy Atom Count: 12
• Complexity: 151

Purity/Quality:

99.9% ^*data from raw suppliers

a-D-Glucose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Monosaccharides and Derivatives
• Canonical SMILES: C(C1C(C(C(C(O1)O)O)O)O)O
• Isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O
• Uses: α-D-Glucose is used:As a reducing agent in the preparation superparamagnetic ferrous oxide (Fe3O4) nanoparticles and silver nanocrystals.As an additive for the formation of isoporous polystyrene-block-poly(4-vinylpyridine) (PS-b-P4VP) diblock copolymer membranes.For glycosylation of cell-penetrating poly(disulfide)s (CPDs) with improved solubility to achieve multifunctional cellular uptake.As a precursor in the synthesis of metal/carbon nanohybrids under hydrothermal conditions. D-(+)-Glucose is a common natural sugar involved in processes such as energy production, glycosylation, and formation of glycans that provide structure to cells. Glucose is involved in a detrimentatl process in cells called glycation. Glucose is used as a supplement for cell culture and in numerous cellular processes and molecular biology applications.

Technology Process of (2S,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

There total 153 articles about (2S,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol 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:

4-nitrophenyl-α-D-glucopyranoside (3767-28-0) → alpha-D-glucopyranose (492-62-6) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0)

Guidance literature:

With B_. cereus oligo-1,6-glucosidase EC 3.2.1.10; In phosphate buffer; at 35 ℃; pH=7.0; Further Variations:; Reagents; Enzyme kinetics;

DOI:10.1271/bbb.65.2058

Reference yield:

Salidroside (10338-51-9) → alpha-D-glucopyranose (492-62-6)

Guidance literature:

With hydrogenchloride; water; In methanol; at 90 ℃; for 3h;

DOI:10.1016/j.phytochem.2011.07.008

Reference yield:

p-(2'-hydroxyethyl)-phenol β-D-pyranoglucoside (38954-02-8) → alpha-D-glucopyranose (492-62-6)

Guidance literature:

With hydrogenchloride; water; In methanol; at 90 ℃; for 3h;

DOI:10.1016/j.phytochem.2011.07.008

upstream raw materials:

D-glucose

diazomethane

methanol

nonacosa-O-methylagrimoniin

Downstream raw materials:

1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose

N-phenethyl-β-D-glucopyranosylamine

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

2-acetyl-neopentylpyrrole

Refernces

• 1、 Takahashi, Kazuki,Terauchi, Issei,Ono, Marie,Satoh, Hiroshi,Ueda, Makoto. "Microbial production of neryl-α-D-glucopyranoside from nerol by Agrobacterium sp. M-12 reflects glucosyl transfer activity". . p. 2205 - 2211. Retrieved 2018.
• 2、 Zhang, Qikun,Kang, Junqing,Yang, Bing,Zhao, Leizhen,Hou, Zhaosheng,Tang, Bo. "Immobilized cellulase on Fe3O4 nanoparticles as a magnetically recoverable biocatalyst for the decomposition of corncob". . p. 389 - 397. Retrieved 2016.
• 3、 Matsui, Hirokazu,Tanaka, Yoshimasa,Brewer, Curtis F.,Blanchard, John S.,Hehre, Edward J.. "Hydrolysis of α- and β-D-glucosyl fluoride by individual glucosidases: new evidence for separately controlled "plastic" and "conserved" phases in glycosylase catalysis". . p. 45 - 56. Retrieved 1993.
• 4、 Santhanaraj, Daniel,Rover, Marjorie R.,Resasco, Daniel E.,Brown, Robert C.,Crossley, Steven. "Gluconic acid from biomass fast pyrolysis oils: Specialty chemicals from the thermochemical conversion of biomass". . p. 3132 - 3137. Retrieved 2014.
• 5、 Zakharenko, A. M.,Kusaykin, M. I.,Kovalchuk, S. N.,Sova, V. V.,Silchenko, A. S.,Anastyuk, S. D.,Rasskazov, V. A.,Zvyagintseva, T. N.,Belik, A. A.,Ly, Bui Minh. "Catalytic properties and amino acid sequence of endo-1→3-β-D- glucanase from the marine mollusk Tapes literata". . p. 878 - 888,11. Retrieved 2012.
• 6、 Pfeiffer, Martin,Wildberger, Patricia,Nidetzky, Bernd. "Yihx-encoded haloacid dehalogenase-like phosphatase HAD4 from Escherichia coli is a specific α-d-glucose 1-phosphate hydrolase useful for substrate-selective sugar phosphate transformations". . p. 39 - 46. Retrieved 2014.
• 7、 Komatsu, Teruyuki,Terada, Hiromi,Kobayashi, Nao. "Protein nanotubes with an enzyme interior surface". . p. 1849 - 1854. Retrieved 2011.
• 8、 O'Neill, Ellis C.,Pergolizzi, Giulia,Stevenson, Clare E.M.,Lawson, David M.,Nepogodiev, Sergey A.,Field, Robert A.. "Cellodextrin phosphorylase from Ruminiclostridium thermocellum: X-ray crystal structure and substrate specificity analysis". . p. 118 - 132. Retrieved 2017.
• 9、 Hegde,Patel,Gullo,Horan,King,Gentile,Wagman,Puar,Loebenberg. "A novel macrolactam-disaccharide antifungal antibiotic taxonomy, fermentation, isolation, physico-chemical properties, structure elucidation and biological activity". . p. 1109 - 1115. Retrieved 1993.
• 10、 Huang, Bo,Fu, Hui-Zheng,Chen, Wei-Kang,Luo, Yue-Hua,Ma, Shuang-Cheng. "Hepatoprotective triterpenoid saponins from Callicarpa nudiflora". . p. 695 - 699. Retrieved 2014.