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:

99% ^*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

• 1、 Kakitsubata, Yuhei,Aramaki, Rikiya,Nishioka, Kyosuke,Wakao, Masahiro,Suda, Yasuo. "Toward the construction of dermatan sulfate (DS) partial disaccharide library: Efficient synthesis of building blocks, common intermediate, and ligand conjugate of type-B DS disaccharide". . p. 1154 - 1157. Retrieved 2016.
• 2、 -. "METHODS FOR MAKING DARUNAVIR P2-LIGAND PRECURSORS". Paragraph 0008; 0022; 0033. . Retrieved 2022/02/28.
• 3、 Matovi?, Jelena,J?rvinen, Juulia,Sokka, Iris K.,Imlimthan, Surachet,Raitanen, Jan-Erik,Montaser, Ahmed,Maaheimo, Hannu,Huttunen, Kristiina M.,Per?niemi, Sirpa,Airaksinen, Anu J.,Sarparanta, Mirkka,Johansson, Mikael P.,Rautio, Jarkko,Ekholm, Filip S.. "Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and in Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates". . p. 285 - 304. Retrieved 2020/12/21.