1,2-O-Isopropylidene-D-glucofuranose

Base Information

• Chemical Name: 1,2-O-Isopropylidene-D-glucofuranose
• CAS No.: 18549-40-1
• Deprecated CAS: 108061-08-1,582-51-4,902458-58-6,1195621-16-9,934708-33-5
• Molecular Formula: C9H16O6
• Molecular Weight: 220.222
• Hs Code.: 29329990
• European Community (EC) Number: 242-420-9
• DSSTox Substance ID: DTXSID80885054
• Nikkaji Number: J222.242F
• Wikidata: Q72485942
• Mol file: 18549-40-1.mol

Synonyms:1,2-O-isopropylidene-D-glucofuranose;1,2-O-isopropylidene-D-glucofuranose, 1-(13)C-labeled;1,2-O-isopropylidene-D-glucofuranose, 6-(13)C-labeled;monoacetone-glucose

Chemical Property of 1,2-O-Isopropylidene-D-glucofuranose

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 6.62E-09mmHg at 25°C
• Melting Point: 159-160 °C(lit.)
• Refractive Index: 1.518
• Boiling Point: 422.4 °C at 760 mmHg
• PKA: 13.19±0.60(Predicted)
• Flash Point: 209.3 °C
• PSA: 88.38000
• Density: 1.358 g/cm³
• LogP: -1.42310
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 220.09468823
• Heavy Atom Count: 15
• Complexity: 243

Purity/Quality:

99% ^*data from raw suppliers

1,2-O-Isopropylidene-a-D-glucofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(C(OC2O1)C(CO)O)O)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H]([C@H](O[C@@H]2O1)[C@@H](CO)O)O)C
• Uses: 1,2-O-Isopropylidene-alpha-D-glucofuranose is used in method for preparaing Tribenoside.

Technology Process of 1,2-O-Isopropylidene-D-glucofuranose

There total 51 articles about 1,2-O-Isopropylidene-D-glucofuranose 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: 100.0%

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,2-O-isopropylidene-α-D-glucofuranose (18549-40-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In water; acetonitrile; at 20 ℃; for 4h; selective removal of acetal group; other acetals and thioacetals of carbohydrates;

DOI:10.1016/0008-6215(95)00065-2

Reference yield: 99.0%

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 2,2,4-trimethyl-1,3-dioxolane (1193-11-9,116944-25-3) + 1,2-O-isopropylidene-α-D-glucofuranose (18549-40-1)

Guidance literature:

With propylene glycol; toluene-4-sulfonic acid; In dichloromethane; for 1h;

DOI:10.1016/S0008-6215(00)90486-5

Reference yield: 94.0%

(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(2-methoxy-ethoxymethoxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole → 1,2-O-isopropylidene-α-D-glucofuranose (18549-40-1)

Guidance literature:

With cerium(III) chloride; In acetonitrile; for 1.5h; Heating;

DOI:10.1021/ol015585w

upstream raw materials:

D-glucose

acetone

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

D-glucurono-3,6-lactone acetonide

Downstream raw materials:

1,2-di-O-isopropylidene-5,6-O-thiocarbonyl-α-D-glucofuranose

6-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranoside

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

Refernces

• 1、 Kalmode, Hanuman P.,Maity, Dilip K.,Bhate, Prakash M.. "Thermal and Lewis acid promoted intramolecular Diels-Alder reaction of furanose tethered 1,3,9-decatriene systems: A synthetic and computational investigation". . p. 63445 - 63462. Retrieved 2016.
• 2、 Zhang, Ben-li,Billault, Isabelle,Li, Xiaobao,Mabon, Francoise,Remaud, Gerald,Martin, Maryvonne L.. "Hydrogen isotopic profile in the characterization of sugars. Influence of the metabolic pathway". . p. 1574 - 1580. Retrieved 2002.
• 3、 Roseman. "-". . p. 4467. Retrieved 1952.
• 4、 Gautam,Kumar, D. Naveen,Rao, B. Venkateswara. "Chiron approach for the synthesis of (1S,2R,5R,7S)-2-hydroxy-exo-brevicomin". . p. 819 - 821. Retrieved 2006.
• 5、 Buchanan,Oakes. "-". . p. 242,247. Retrieved 1965.
• 6、 Mehltretter et al.. "-". . p. 2424,2426. Retrieved 1951.
• 7、 Nikam, Rahul R.,Gore, Kiran R.. "A mild and convenient approach for selective acetonide cleavage involved in carbohydrate synthesis using PPA-SiO2". . p. 63 - 74. Retrieved 2020.
• 8、 Garcia Fernandez,Ortiz Mellet,Moreno Marin,Fuentes. "A mild and efficient procedure to remove acetal and dithioacetal protecting groups in carbohydrate derivatives using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone". . p. 263 - 268. Retrieved 1995.
• 9、 Benedekovi?, Goran,Popsavin, Mirjana,Radulovi?, Niko S.,Stojanovi?-Radi?, Zorica,Farkas, Sándor,Francuz, Jovana,Popsavin, Velimir. "Synthesis and antimicrobial activity of (?)-cleistenolide and analogues". . . Retrieved 2020/12/07.
• 10、 B?aszczyk, Jaros?aw,Bujnicki, Bogdan,Chmielewski, Marek,Drabowicz, Józef. "Diastereoisomerically pure, (S)-O-1,2-O-isopropyli dene-(5-O-α-d-glucofuranosyl) t-butanesulfinate: Synthesis, crystal structure, absolute configuration and reactivity". . . Retrieved 2020/09/16.