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

Description

Diaceton-alpha-D-mannofuranose, also known as 2,3:5,6-Di-O-isopropylidene-alpha-D-mannofuranose, is a white to light yellow crystalline powder that serves as a valuable research chemical. It is a derivative of alpha-D-mannofuranose, a monosaccharide that plays a significant role in various biological processes.

Uses

Used in Pharmaceutical Industry:
Diaceton-alpha-D-mannofuranose is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block for the development of new drugs with potential applications in treating various diseases.
Used in Chemical Synthesis:
Diaceton-alpha-D-mannofuranose is used as a synthetic building block for the preparation of complex organic molecules. Its ability to be modified and incorporated into larger structures makes it a valuable tool in the field of organic chemistry.
Used in Research and Development:
As a research chemical, Diaceton-alpha-D-mannofuranose is used in the development of new methodologies and techniques in organic synthesis. It helps researchers understand the reactivity and properties of similar compounds, leading to the discovery of novel applications and advancements in the field.
Used in Synthesis of Ovalicin:
Diaceton-alpha-D-mannofuranose is used as a starting material in the synthesis of ovalicin, a natural product with potential biological activities. Its role in the synthesis process highlights its importance in the development of new pharmaceutical agents.
Used in Synthesis of Hikizimycin Sugar Core:
Diaceton-alpha-D-mannofuranose is also used in the synthesis of the sugar core of hikizimycin, an antibiotic with potent antibacterial properties. Its involvement in the synthesis of such an important compound underscores its utility in the pharmaceutical industry.

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

• 35023-80-4 2,3:5,6-di-O-isopropylidene-D-mannose oxime 
• 530-26-7 D-Mannose 
• 67-64-1 acetone 
• 3458-28-4 D-Mannose 
• 7306-64-1 2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone 
• 250127-86-7 2,3:5,6-di-O-isopropylidene-1-O-(allenyl)-α-D-mannofuranoside 
• 77-76-9 2,2-dimethoxy-propane 
• 36574-21-7 α-D-mannose 
• 250127-79-8 (3aS,4R,6S,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-(prop-2-ynyloxy)tetrahydrofuro[3,4-d][1,3]dioxole 
• 54515-83-2 2,3:5,6-di-O-isopropylidene-1-O-(prop-2-enyl)-α-D-mannofuranoside 
• 177562-09-3 1-O-(2-phenylacetyl)-2,3;5,6-di-O-isopropylidene-α-D-mannofuranose 
• 582-52-5 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 
• 116-11-0 2-Methoxypropene 
• 75-52-5 nitromethane 

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 
• 76679-45-3 Benzyl-2,3-di-O-benzyl-5-O-(2,3:5,6-di-O-isopropyliden-β-D-mannofuranosyl)-β-D-ribofuranosid 
• 76679-42-0 Benzyl-2,3-di-O-benzyl-5-O-(2,3:5,6-di-O-isopropyliden-α-D-mannofuranosyl)-β-D-ribofuranosid 
• 17087-84-2 (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 
• 94898-41-6 (3aS,4R,6R,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole 
• 79241-07-9 (R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan 
• 7306-64-1 2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone 
• 6160-67-4 (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 
• 6160-67-4 (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 
• 869354-98-3 benzyl 2,3: 5,6-di-O-isopropylidene-D-mannofuranoside 
• 54469-08-8 benzyl 2,3:5,6-di-O-isopropylidene-β-D-mannofuranoside 
• 54469-08-8 phenylmethyl 2,3:5,6-di-O-(1-methylethylidene)-α-D-mannofuranoside 
• 157687-80-4 diphenyl (2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl) phosphate 

Relevant articles and documents

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

Visible-Light-Induced Pd-Catalyzed Radical Strategy for Constructing C-Vinyl Glycosides

A novel visible-light-induced palladium-catalyzed Heck reaction for bromine sugars and aryl olefins with high regio- and stereochemistry selectivity for the preparation of C-glycosyl styrene is described. This reaction takes place in one step at room temperature by using a simple and readily available starting material. This protocol can be scaled up to a wide range of glycosyl bromide donors and aryl olefin substrates. Mechanistic studies indicate that a radical addition pathway is involved.

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.