Diaceton-alpha-D-mannofuranose

Base Information

• Chemical Name: Diaceton-alpha-D-mannofuranose
• CAS No.: 14131-84-1
• Molecular Formula: C12H20O6
• Molecular Weight: 260.287
• Hs Code.: 29400090
• NSC Number: 89873,25268
• Mol file: 14131-84-1.mol

Synonyms:14131-84-1;Diaceton-alpha-D-mannofuranose;2,3:5,6-Di-O-isopropylidene-D-gulofuranose;6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol;34685-42-2;Talofuranose, 2,3:5,6-di-O-isopropylidene-, .alpha.-D-;NSC25268;NCIOpen2_006365;7757-38-2;SCHEMBL3759882;JWWCLCNPTZHVLF-UHFFFAOYSA-N;NSC89873;NSC-25268;NSC-89873;AKOS015914118;FT-0624590

Chemical Property of Diaceton-alpha-D-mannofuranose

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.31E-06mmHg at 25°C
• Melting Point: 125-126 °C (dec.)(lit.)
• Refractive Index: 24 ° (C=1, Acetone)
• Boiling Point: 359.3 °C at 760 mmHg
• PKA: 11.97±0.60(Predicted)
• Flash Point: 171.1 °C
• PSA: 66.38000
• Density: 1.214 g/cm³
• LogP: 0.37520
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: Acetone (Slightly, Sonicated), Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in acetone, methanol, water.
• 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

2,3:5,6-Di-O-isopropylidene-a-D-mannofuranose ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(OCC(O1)C2C3C(C(O2)O)OC(O3)(C)C)C
• Uses: 2,3:5,6-Di-O-isopropylidene-alpha-D-mannofuranose is a useful research chemical. 2,3:5,6-Di-O-isopropylidene-alpha-D-mannofuranose is used in the syntheses of ovalicin1 and of the sugar core of hikizimycin.

Technology Process of Diaceton-alpha-D-mannofuranose

There total 47 articles about Diaceton-alpha-D-mannofuranose 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%

D-Mannose (530-26-7) + 2,2-dimethoxy-propane (77-76-9) → 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose (7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 1h;

DOI:10.1002/anie.202002295

Reference yield: 100.0%

D-Mannose (530-26-7) + acetone (67-64-1) → 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose (7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4)

Guidance literature:

With indium(III) triflate; for 0.166667h; Reflux;

DOI:10.1080/07328300802458970

Reference yield: 97.0%

2,3:5,6-di-O-isopropylidene-L-gulonolactone (7306-64-1) → 2,3:5,6-di-O-isopropylidene-D-mannofuranose (7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 0.666667h; Inert atmosphere;

DOI:10.1002/asia.200800406

upstream raw materials:

2,3:5,6-di-O-isopropylidene-D-mannose oxime

D-Mannose

acetone

D-Mannose

Downstream raw materials:

(3aS,4R,6R,6aS)-4-chloro-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

(3aS,6R,6aS)-4-Chloro-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

benzyl 2,3: 5,6-di-O-isopropylidene-D-mannofuranoside

benzyl 2,3:5,6-di-O-isopropylidene-β-D-mannofuranoside

Refernces

• 1、 Ameur, Nassima,Gamboa Marin, Oscar Javier,Gauthier, Charles,Gormand, Paul,Hussain, Nazar,Ravicoularamin, Gokulakrishnan,Sauvageau, Janelle. "Total Synthesis of 6-Amino-2,6-dideoxy-α-Kdo from d -Mannose". supporting information. . Retrieved 2020/07/27.
• 2、 Carell, Thomas,Ensfelder, Timm T.,Heiss, Matthias,Hillmeier, Markus,Kellner, Stefanie,Müller, Markus,Michalakis, Stylianos,Sch?n, Alexander,Scheel, Constanze,Thumbs, Peter,Wagner, Mirko. "Synthesis of Galactosyl-Queuosine and Distribution of Hypermodified Q-Nucleosides in Mouse Tissues". supporting information. p. 12352 - 12356. Retrieved 2020/04/27.