14131-84-1

Basic information

• Product Name: Diaceton-alpha-D-mannofuranose
• Synonyms: diisopropylidenemannofuranose;Diaceton-alpha-D-mannofuranose;DIACETONE-D-MANNOSE;D-Mannose diacetonide;2,3:5,6-DI-O-ISOPROPYLIDENE-A-D-MANNOFURANOSE;2,3:5,6-DI-O-ISOPROPYLIDENE-A-D-MANNOPYRANOSE;(+)-2,3:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSE;2,3,5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSE
• CAS NO: 14131-84-1
• Molecular Formula: C₁₂H₂₀O₆
• Molecular Weight: 260.28
• EINECS: 1312995-182-4
• Product Categories: 13C & 2H Sugars;Biochemistry;O-Substituted Sugars;Sugars;aldehydes;Carbohydrates & Derivatives
• Mol File: 14131-84-1.mol
• Article Data: 90

Chemical Properties

• Melting Point: 125-126 °C (dec.)(lit.)
• Boiling Point: 363.54°C (rough estimate)
• Flash Point: 171.1 °C
• Appearance: White to Off-white/Powder
• Density: 1.2377 (rough estimate)
• Vapor Pressure: 1.31E-06mmHg at 25°C
• Refractive Index: 24 ° (C=1, Acetone)
• Storage Temp.: 2-8°C
• Solubility: Acetone (Slightly, Sonicated), Chloroform (Slightly), Methanol (Slightly)
• PKA: 11.97±0.60(Predicted)
• Water Solubility: Soluble in acetone, methanol, water.
• Sensitive: Hygroscopic
• BRN: 84382
• CAS DataBase Reference: Diaceton-alpha-D-mannofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: Diaceton-alpha-D-mannofuranose(14131-84-1)
• EPA Substance Registry System: Diaceton-alpha-D-mannofuranose(14131-84-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37-26
• WGK Germany: 3
• F: 3-21
• Hazardous Substances Data: 14131-84-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 14131-84-1 differently. You can refer to the following data:
1. 2,3:5,6-Di-O-isopropylidene-alpha-D-mannofuranose is a useful research chemical.
2. 2,3:5,6-Di-O-isopropylidene-alpha-D-mannofuranose is used in the syntheses of ovalicin1 and of the sugar core of hikizimycin.

Chemical Properties

white to light yellow crystal powde

InChI:InChI=1/C12H20O6/c1-11(2)14-5-6(16-11)7-8-9(10(13)15-7)18-12(3,4)17-8/h6-10,13H,5H2,1-4H3/t6-,7-,8+,9+,10+/m1/s1

Upstream product

• 3458-28-4 D-Mannose 
• 77-76-9 2,2-dimethoxy-propane 
• 530-26-7 D-Mannose 
• 116-11-0 2-Methoxypropene 
• 67-64-1 acetone 
• 35023-80-4 2,3:5,6-di-O-isopropylidene-D-mannose oxime 
• 50-81-7 ascorbic acid 
• 1128-23-0 L-gulono-1,4-lactone 
• 7306-64-1 2,3:5,6-di-O-isopropylidene-L-gulonolactone 
• 49561-21-9 (3aR,6S,6aR)-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 
• 75-52-5 nitromethane 
• 5328-37-0 L-arabinose 
• 582-52-5 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 
• 177562-09-3 1-O-(2-phenylacetyl)-2,3;5,6-di-O-isopropylidene-α-D-mannofuranose 

Downstream Products

• 138034-65-8 (1R)-2,3-5,6-di-O-isopropylidene-1-C-phenyl-D-mannitol 
• 138034-65-8 (R)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)((4S,5R)-5-((S)-hydroxy (phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol 
• 14440-57-4 1-O-acetyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 3458-28-4 D-Mannose 
• 640285-46-7 (3aS,6R,7R,7aS)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4,7-diol 
• 177562-07-1 1-O-butanoyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 177562-07-1 1-O-butanoyl-2,3:5,6-di-O-isopropylidene-β-D-mannofuranose 
• 871948-11-7 (E)-3,4:6,7-di-O-isopropylidene-1,2-dideoxy-1-phenylsulfanyl-D-manno-hept-1-enitol 

Relevant articles and documents

Aspartic Acid Forming α-Ketoacid-Hydroxylamine (KAHA) Ligations with (S)-4,4-Difluoro-5-oxaproline

The α-ketoacid-hydroxylamine (KAHA) ligation allows the coupling of unprotected peptide segments. Currently, the most applied hydroxylamine is the 5-membered cyclic hydroxylamine (S)-5-oxaproline, which forms a homoserine ester as the primary ligation product. In order to access native aspartic acid residues at the ligation site, we synthesized a 4,4-difluoro version of this monomer. Upon KAHA ligation, the resulting difluoro alcohol hydrolyzes to an aspartic acid residue with little or no formation of aspartamide. We applied this monomer for the synthesis of the hormone peptides glucagon and an insulin variant, and as well for segment ligation of the peptides UbcH5a and SUMO3.

Total Synthesis of 6-Amino-2,6-dideoxy-α-Kdo from d -Mannose

3-Deoxy-d-manno-oct-2-ulosonic acid (Kdo) biosynthetic pathway is a promising target in antibacterial drug discovery. Herein, we report the total synthesis of 6-amino-2,6-dideoxy-α-Kdo in 15 steps from d-mannose as a potential inhibitor of Kdo-processing

Discovery and Structure-Activity Relationships of Novel Template, Truncated 1′-Homologated Adenosine Derivatives as Pure Dual PPARγ/δModulators

Following our report that A3 adenosine receptor (AR) antagonist 1 exhibited a polypharmacological profile as a dual modulator of peroxisome proliferator-activated receptor (PPAR)γ/δ, we discovered a new template, 1′-homologated adenosine analogues 4a-4t, as dual PPARγ/δmodulators without AR binding. Removal of binding affinity to A3AR was achieved by 1′-homologation, and PPARγ/δdual modulation was derived from the structural similarity between the target nucleosides and PPAR modulator drug, rosiglitazone. All the final nucleosides were devoid of AR-binding affinity and exhibited high binding affinities to PPARγ/δbut lacked PPARα binding. 2-Cl derivatives exhibited dual receptor-binding affinity to PPARγ/δ, which was absent for the corresponding 2-H derivatives. 2-Propynyl substitution prevented PPARδ-binding affinity but preserved PPARγaffinity, indicating that the C2 position defines a pharmacophore for selective PPARγligand designs. PPARγ/δdual modulators functioning as both PPARγpartial agonists and PPARδantagonists promoted adiponectin production, suggesting their therapeutic potential against hypoadiponectinemia-associated cancer and metabolic diseases.