1,2:5,6-Diisopropylidene-alpha-D-glucofuranose

Base Information

• Chemical Name: 1,2:5,6-Diisopropylidene-alpha-D-glucofuranose
• CAS No.: 582-52-5
• Molecular Formula: C12H20O6
• Molecular Weight: 260.287
• Hs Code.: 29329970
• European Community (EC) Number: 209-486-0
• Nikkaji Number: J439.632D
• Mol file: 582-52-5.mol

Synonyms:1,2-5,6-di-O-isopropylidene-D-glucofuranose;1,2-5,6-di-O-isopropylidene-D-glucofuranose, potassium salt;diacetone glucose

Chemical Property of 1,2:5,6-Diisopropylidene-alpha-D-glucofuranose

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 9.94E-07mmHg at 25°C
• Melting Point: 110-111 °C(lit.)
• Refractive Index: -18.5 ° (C=5, H2O)
• Boiling Point: 362.8 °C at 760 mmHg
• PKA: 13.15±0.60(Predicted)
• Flash Point: 173.2 °C
• PSA: 66.38000
• Density: 1.214 g/cm³
• LogP: 0.37520
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
• Water Solubility.: slightly soluble
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 260.12598835
• Heavy Atom Count: 18
• Complexity: 342

Purity/Quality:

98% ^*data from raw suppliers

1,2,5,6-Di-O-isopropylidene-a-L-glucofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Monosaccharides and Derivatives
• Canonical SMILES: CC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)O)C
• Isomeric SMILES: CC1(OC[C@H](O1)[C@@H]2[C@@H]([C@@H]3[C@H](O2)OC(O3)(C)C)O)C
• Uses: It is mainly used in biochemical reaction and used as medicine intermediate. It is used in synthesize for below products: L-gulose;1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose; Alllose; ;1,2:5,6-Double-O-Isopropylidene-3-C-(1-Methoxycarbonyl)Ethide-alfa-D-Furanose) ;1,2:5,6-Di-O-isopropylidene-a-D-ribo-hexofuranose-3-ulose;6-deoxy idose. 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose is a compound useful in organic synthesis.

Technology Process of 1,2:5,6-Diisopropylidene-alpha-D-glucofuranose

There total 151 articles about 1,2:5,6-Diisopropylidene-alpha-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%

3-O-(2-azidomethyl)phenylacetyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (428500-97-4) → 1,4-dihydro-3(2H)-isoquinolinone (24331-94-0) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Guidance literature:

With hydrogen; Lindlar's catalyst; In methanol; at 20 ℃; for 3h;

DOI:10.1016/S0008-6215(01)00292-0

Reference yield: 100.0%

3-O-acetyl-1,2,5,6-di-isopropylidene-α-D-glucofuranose (29586-98-9) → 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose (582-52-5,2595-05-3,10368-86-2,13100-30-6,14686-89-6,23262-79-5,26597-74-0,26623-15-4,38166-58-4,38166-60-8,79943-22-9,83730-28-3) + acetic acid methyl ester (79-20-9)

Guidance literature:

With n-butylstannoic acid; In methanol; at 65.4 ℃; for 2h;

DOI:10.1016/S0040-4039(98)00241-X

Reference yield: 86.0%

(3aR,5R,6S,6aR)-6-(3,5-Dimethoxy-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole → 3,5-dimethoxybenzaldehdye (7311-34-4) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; for 2.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)90593-9

upstream raw materials:

D-glucose

acetone

(3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-nitrooxy-tetrahydro-furo[2,3-d][1,3]dioxole

Diethyl-thiocarbamic acid O-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester

Downstream raw materials:

O³-butyryl-O¹,O²;O⁵,O⁶-diisopropylidene-α-D-glucofuranose

O³-diphenoxyphosphino-O¹,O²;O⁵,O⁶-diisopropylidene-α-D-glucofuranose

1,2:5,6-di-O-isopropylidene-3-O-trityl-α-D-glucofuranose

1,2:5,6-di-O-isopropylidene-3-(N-phenylthioxocarbamoyl)-α-D-glucofuranose

Refernces

Ionic-liquid supported rapid synthesis of an: N -glycan core pentasaccharide on a 10 g scale

10.1039/c8ob01046c

The research focuses on the rapid synthesis of N-glycan core pentasaccharide using a new Ionic Liquid-Supported Oligosaccharide Synthesis (ILSOS) strategy. The study introduces an efficient method for assembling complex hetero-branched oligosaccharides on a multi-gram scale, which is a significant advancement in the field of glycobiology. The experiments involved the use of various reactants, including 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, NapBr, NaH, DMF, TsOH, MeCNaq, Ac2O, Pyr, H2NC3H6NMe2, THF, CNCCl3, DBU, TMSOTf, MeONa, PhCH(OMe)2, Tf2O, Pyr, NaNO2, DMF, BnBr, DDQ, DCM, MeOH, BH3THF, Bu2BOTf, CAN, and 80% MeCNaq, among others. The synthesis process was monitored and analyzed using techniques such as TLC, NMR spectroscopy, HPLC, and mass spectrometry to ensure the purity and successful assembly of the target pentasaccharide. The new ILSOS strategy allowed for the orthogonal and efficient removal of the ionic liquid support and demonstrated the potential for large-scale preparation, which addresses previous limitations in the field.

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