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

Base Information

• Chemical Name: (2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
• CAS No.: 492-61-5
• Deprecated CAS: 108942-17-2,28905-12-6,492-64-8,50986-29-3,53991-51-8,28905-12-6,50986-29-3,53991-51-8
• Molecular Formula: C6H12 O6
• Molecular Weight: 180.158
• European Community (EC) Number: 232-601-0,207-756-2,232-725-5
• NSC Number: 759603
• UNII: J4R00M814D
• DSSTox Substance ID: DTXSID70883403
• Nikkaji Number: J44.213E
• Wikidata: Q23905968
• NCI Thesaurus Code: C61650
• RXCUI: 1442190
• Metabolomics Workbench ID: 37288
• ChEMBL ID: CHEMBL1614854
• Mol file: 492-61-5.mol

Synonyms:beta-D-glucose;beta-D-glucopyranose;492-61-5;glucoside;beta-Dextrose;b-d-glucose;.beta.-D-Glucopyranose;beta-glucose;Curdlan;28905-12-6;Oxidase, glucose;(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol;.beta.-D-Glucose;Glucose, (beta-D)-Isomer;(2R,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol;.beta.-d-Glucose, anhydrous;UNII-J4R00M814D;Grape sugar;beta-D-Glucopyranose, anhydrous;CHEMBL1614854;CHEBI:15903;9001-37-0;J4R00M814D;EINECS 207-756-2;(+)-Glucose;4-Morpholineacetic acid, a-Methylene-, Methyl ester;128009-02-9;133947-06-5;54724-00-4;ZYMOSAN;Glucodin;Meritose;136760-05-9;anhydrous glucose;Clintose L;CPC hydrate;Roferose ST;Clearsweet 95;Glucosides;Staleydex 95M;.beta.-D-ribo-Hexopyranose, 1,6-anhydro-3-deoxy-2-O-phenyl-4-O-(phenylmethyl)-;BGC;mikrotsid;Corylophyline;Callose;Microcid;Notatin;9010-72-4;beta -d-glucose;beta-D-Glc;Deoxin-1;1,3-beta-D-Glucan;beta-(1,3)-glucan;beta-D-Glucose oxidase;I(2)-D-Glucopyranose;Glucose aerodehydrogenase;Beta-D-glucose anhydrous;Glucose oxidase [USAN];Beta-d-glucose, anhydrous;6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrol;GLUCOSE, BETA-D-;D07ONX;(1,2-beta-D-glucosyl)n;(1->2)-beta-D-glucan;(1->3)-beta-D-glucan;(1->4)-beta-D-glucan;(1->6)-beta-D-glucan;GLUCOSE, .BETA.-D;SCHEMBL25601;(1->2)-beta-D-glucopyranan;(1->3)-beta-D-glucopyranan;(1->4)-beta-D-glucopyranan;(1->6)-beta-D-glucopyranan;CCRIS 3425;UNII-0T8392U5N1;CHEBI:18246;CHEBI:27380;CHEBI:27517;CHEBI:37671;DTXSID70883403;Pharmakon1600-01300015;.BETA.-D-GLUCOSE ANHYDROUS;D-glucose;glucose;EINECS 232-601-0;BDBM50240803;beta-D-Glucose:quinone oxidoreductase;MFCD00063989;NSC759603;beta-D-Glucopyranose aerodehydrogenase;AKOS016010209;DB02379;NSC-759603;YC46078;beta-D-glucose: oxygen 1-oxidoreductase;NCGC00263446-02;Beta-D-glucose(contains alpha-D-glucose);BS-22220;HY-121965;CS-0083772;G0047;C00221;D90709;E.C. 1.1.3.4;AE-562/43459286;W-202206;Glucose oxidase (EC 1.1.3.4) from aspergillus niger;Q23905968;WURCS=2.0/1,1,0/[a2122h-1b_1-5]/1/;50986-29-3

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

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.83E-08mmHg at 25°C
• Melting Point: 156-158 °C
• Boiling Point: 410.8 °C at 760 mmHg
• PKA: 12.12±0.70(Predicted)
• Flash Point: 202.2 °C
• PSA: 110.38000
• Density: 1.732 g/cm³
• LogP: -3.22140
• Storage Temp.: 2-8°C
• 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:

98%, ^*data from raw suppliers

b-D-Glucose ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: UVCB,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
• Recent ClinicalTrials: Adjuvant Therapy With an Alpha-lactalbumin Vaccine in Triple-Negative Breast Cancer
• Uses: Replenisher (fluid and nutrient).

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

There total 819 articles about (2R,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: 88.0%

cellulose (9004-34-6) → β-D-glucose (492-61-5)

Guidance literature:

With hydrogenchloride; water; at 179.84 ℃; for 0.516667h; Reagent/catalyst;

DOI:10.1021/cs300845f

Reference yield: 73.0%

senedensiscin A → β-D-glucose (492-61-5) + (1S,4S,5R,6R,7S,10S)-trihydroxyeudesmane (227471-20-7)

Guidance literature:

senedensiscin A; With potassium carbonate; In methanol; at 20 ℃; for 10h;

With hydrogenchloride; water; In methanol; at 20 ℃;

DOI:10.1016/j.tet.2013.10.047

Reference yield: 57.0%

Cellobiose (13360-52-6) → β-D-glucose (492-61-5) + D-sorbitol (50-70-4) + β-D-Glcp-(1->4)-D-glucitol (535-94-4)

Guidance literature:

With water; hydrogen; at 180 ℃; for 1h; under 37503.8 Torr; High pressure;

DOI:10.1007/s11426-018-9321-0

upstream raw materials:

alpha-D-glucopyranose

isoquercetin

methanol

1-O-(glycylglycylglycyl)-β-D-glucopyranose

Downstream raw materials:

D-(+)-lactose

gluconic acid

levoglucosan

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

Refernces

• 1、 Yean, Min Hye,Kim, Ju Sun,Kang, Sam Sik,Kim, Yeong Shik. "A new megastigmane glucoside and three new flavonoid glycosides from spiraea prunifolia var. simpliciflora". . p. 1123 - 1131. Retrieved 2014.
• 2、 Wang, Shu-Qi,Zhu, Xiao-Feng,Wang, Xiao-Ning,Shen, Tao,Xiang, Feng,Lou, Hong-Xiang. "Flavonoids from Malus hupehensis and their cardioprotective effects against doxorubicin-induced toxicity in H9c2 cells". . p. 119 - 125. Retrieved 2013.
• 3、 Huang, Shuai,Zhou, Xian-Li,Wang, Hong-Yan,Wang, Cui-Juan,Zhou, Xiao-Li,Xiao, Feng,Weng, Jie. "Eremophilane derivatives from Senecio dianthus". . p. 711 - 718. Retrieved 2013.
• 4、 Pan, Qi-Ming,Zhang, Gui-Jie,Huang, Ri-Zhen,Pan, Ying-Ming,Wang, Heng-Shan,Liang, Dong. "Cytisine-type alkaloids and flavonoids from the rhizomes of Sophora tonkinensis". . p. 429 - 435. Retrieved 2016.
• 5、 Muhit, Md. Abdul,Umehara, Kaoru,Mori-Yasumoto, Kanami,Noguchi, Hiroshi. "Furofuran Lignan Glucosides with Estrogen-Inhibitory Properties from the Bangladeshi Medicinal Plant Terminalia citrina". . p. 1298 - 1307. Retrieved 2016.
• 6、 Lee, Yi-Chun,Chen, Ching-Tien,Chiu, Yu-Ting,Wu, Kevin C.-W.. "An effective cellulose-to-glucose-to-fructose conversion sequence by using enzyme immobilized Fe3O4-loaded mesoporous silica nanoparticles as recyclable biocatalysts". . p. 2153 - 2157. Retrieved 2013.
• 7、 Du, Young Eun,Lee, Jin Su,Kim, Hye Mi,Ahn, Ji-Hye,Jung, In Ho,Ryu, Jong Hoon,Choi, Jung-Hye,Jang, Dae Sik. "Chemical constituents of the roots of Codonopsis lanceolata". . p. 1082 - 1091. Retrieved 2018.
• 8、 Hendra, Rudi,Keller, Paul A.. "Phytochemical Studies on Two Australian Anigozanthos Plant Species". . p. 2141 - 2145. Retrieved 2017.
• 9、 Khan, M. Aasim,Ali,Alam, Prawez. "Phytochemical investigation of the fruit peels of Citrus reticulata Blanco". . p. 610 - 620. Retrieved 2010.
• 10、 Gutierrez, Rosa Martha Perez. "Antihepatotoxic, nephroprotective, and antioxidant activities of phenolic compounds from Satureja macrostema leaves against carbon tetrachloride-induced hepatic damage in mice". . p. 1846 - 1855. Retrieved 2013.