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4064-06-6, Di-acetone-a-D-galactopyranose, CAS: 4064-06-6

DIACETONE-D-GALACTOSE; Diisopropylidenegalactose;
1,2,3,4-di-O-Isopropylidenegalactopyranose; 1,2:3,4-DI-O-ISOPROPYLIDENE-D-GALACTOPYRANOSE;
CAS: 4064-06-6
C12H20O6 / 260.28

双丙酮半乳糖, Di-acetone-a-D-galactopyranose

1,2:3,4-Di-O-isopropylidene-a-D-galactopyranose, also known as diacetone-D-galactose and galactose diacetonide, is a partially protected monosaccharide building block with isopropylidene groups on the 1,2 and 3,4 hydroxyls. The 6-hydroxyl is unprotected and able to undergo a variety of chemical transformations, such as glycosylation acting as a glycosyl acceptor to form 1,6-linked disaccharides.

1,2:3,4-Di-O-isopropylidene-alpha-D-galactopyranose, commonly known as DIOP, is a cyclic acetal that is widely used as a starting material for the synthesis of various biologically active molecules. DIOP is a versatile building block that can be easily modified to suit the requirements of a specific reaction, making it an essential tool for synthetic chemistry. This paper aims to provide an overview of the definition, physical and chemical properties, synthesis, characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations and future directions of 1,2:3,4-Di-O-isopropylidene-alpha-D-galactopyranose.

Synthesis and Characterization:

DIOP is commonly synthesized by reacting galactose with acetone in the presence of an acid catalyst. The reaction proceeds via a hemiketal intermediate, which then undergoes cyclization to form the cyclic acetal DIOP. The purity of DIOP can be determined by various analytical techniques such as NMR, IR, and mass spectrometry.

Analytical Methods:

Various analytical methods can be used to characterize the purity and identity of DIOP. Nuclear Magnetic Resonance (NMR) is a powerful tool for analyzing the structure and purity of DIOP. Other techniques such as Infrared (IR) spectroscopy and Mass Spectrometry (MS) can also be employed to confirm the chemical structure of DIOP and determine its purity.

Biological Properties:

The biological properties of DIOP are yet to be fully characterized. However, it has been shown to exhibit antifungal properties against various fungal strains. Additionally, DIOP has been used as a starting material for the synthesis of various biologically active molecules such as anti-viral agents, anti-inflammatory drugs, and anti-cancer drugs.

Toxicity and Safety in Scientific Experiments:

DIOP is considered to be non-toxic and is generally safe for use in scientific experiments. However, as with any chemical compound, appropriate safety measures must be taken when handling and working with DIOP to ensure the safety of researchers and laboratory personnel.

Applications in Scientific Experiments:

DIOP is widely used as a starting material for the synthesis of various biologically active molecules. It is an essential tool for synthetic chemistry and has been used in the synthesis of various anti-viral agents, anti-inflammatory drugs, and anti-cancer drugs.

Current State of Research:

Research on DIOP is ongoing, with new applications and synthetic routes being developed. Recent research has focused on the synthesis of new derivatives of DIOP and their potential use as pharmaceuticals and agrochemicals.

Potential Implications in Various Fields of Research and Industry:

DIOP has potential applications in various fields of research and industry. Its use as a building block for the synthesis of biologically active molecules makes it an essential tool for medicinal chemistry. Additionally, its use as a starting material for the synthesis of agrochemicals and flavoring agents makes it an important compound for the food and beverage industry.

Limitations and Future Directions:

Although DIOP is a versatile and essential tool for synthetic chemistry, it has certain limitations. One limitation is its relatively high cost compared to other cyclic acetals. Future research can focus on developing new synthetic routes for DIOP that are more cost-effective and environmentally friendly. Additionally, new derivatives of DIOP can be synthesized and their biological properties explored.

Future Directions:

1. Development of new synthetic routes for the synthesis of DIOP.

2. Synthesis of new derivatives of DIOP and exploration of their biological properties.

3. Investigation of the potential use of DIOP in the synthesis of agrochemicals and flavoring agents.

4. Development of more cost-effective and environmentally friendly synthetic routes for DIOP.

5. Exploration of the potential use of DIOP in nanotechnology and material science.

6. Studies on the mechanisms of action of DIOP and its derivatives in various biological systems.

7. Investigation of the potential use of DIOP in medicinal chemistry and drug discovery.

8. Development of new analytical methods for the characterization of DIOP and its derivatives.

9. Synthesis of enantioselective derivatives of DIOP for use in chirality-based synthesis.

10. Exploration of the potential use of DIOP in polymer chemistry and materials science.

CAS Number4064-06-6
Product Name1,2:3,4-Di-O-isopropylidene-alpha-D-galactopyranose
IUPAC Name[(1S,2R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[,6]dodecan-8-yl]methanol
Molecular FormulaC₁₂H₂₀O₆
Molecular Weight260.28 g/mol
Synonyms1,2:3,4-Bis-O-(1-methylethylidene)-α-D-galactopyranose; Diisopropylidenegalactose; 1,2:3,4-Di-O-isopropylidene-D-galactose; NSC 89756;
Canonical SMILESCC1(OC2C(OC3C(C2O1)OC(O3)(C)C)CO)C
Isomeric SMILESCC1(O[C@H]2[C@H](O[C@H]3[C@@H]([C@H]2O1)OC(O3)(C)C)CO)C


Product name: 1,2:3,4-Di-O-isopropylidene-D-galactopyranose

CAS: 4064-06-6       M.F.: C12H20O6       M.W.: 260.28





A white or slightly yellowish syrup



Soluble in CHCl3 and

less soluble in petroleum ether


Appearance of solution

Dissolve 0.5g in 10mL of CHCl3,

and the solution should be clear



Should comply



IR and TLC


Optical Activity

[α]D20 (c = 3% in CHCl3)

-58o ~ -60 o

-59.2 o

Refractive Index


1.4 ~ 1.5



1.13 ~ 1.15


Residue on ignition

Max. 0.5%


Heavy metal

Max. 20ppm


TLC (15%H2SO4-C2H5OH)

One spot



Min. 97%



1. Santoyo Ganzalez F, Baer HH, Carbohyr. Res. 1990, 15, 202, p33
2. Lee YC, Carbohydr. Res. 1982, 16, 101, p39


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