40269-01-0

Basic information

• Product Name: Methyl 3,4-O-Isopropylidene-α-D-galactopyranoside
• Synonyms: Methyl 3,4-O-(1-Methylethylidene)-α-D-galactopyranoside;Methyl 3,4-O-Isopropylidene-α-D-galactopyranoside;NSC 170242;Methyl 3,4-O-(1-Methylethylidene)-a-D-galactopyranoside;Methyl 3,4-O-Isopropylidene-a-D-galactopyranoside
• CAS NO: 40269-01-0
• Molecular Formula: C₁₀H₁₈O₆
• Molecular Weight: 234.24632
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 40269-01-0.mol

Chemical Properties

• Boiling Point: 382.9°C at 760 mmHg
• Flash Point: 185.4°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 1.93E-07mmHg at 25°C
• Refractive Index: 1.513
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: Methyl 3,4-O-Isopropylidene-α-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3,4-O-Isopropylidene-α-D-galactopyranoside(40269-01-0)
• EPA Substance Registry System: Methyl 3,4-O-Isopropylidene-α-D-galactopyranoside(40269-01-0)

Safety Data

• Hazardous Substances Data: 40269-01-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Methyl 3,4-O-Isopropylidene-α-D-galactopyranoside is used as an intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure allows for selective protection of specific functional groups, which is crucial in multi-step synthesis processes. Methyl 3,4-O-Isopropylidene-α-D-galactopyranoside serves as a versatile building block for the development of novel pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 3,4-O-Isopropylidene-α-D-galactopyranoside is used as a key component in the synthesis of glycosidic compounds, which are essential in the development of new drugs targeting various diseases. Methyl 3,4-O-Isopropylidene-α-D-galactopyranoside's ability to form stable glycosidic linkages with other molecules makes it a valuable asset in the design and synthesis of bioactive molecules with potential therapeutic applications.
Used in Chemical Research:
Methyl 3,4-O-Isopropylidene-α-D-galactopyranoside is also employed in chemical research as a model compound for studying the reactivity and selectivity of various synthetic reactions. Its unique structure allows researchers to investigate the influence of protecting groups on reaction outcomes and to develop new synthetic strategies for the preparation of complex organic molecules.
Used in Material Science:
In the field of material science, Methyl 3,4-O-Isopropylidene-α-D-galactopyranoside can be used as a component in the development of novel materials with specific properties. Its ability to form hydrogen bonds and participate in various non-covalent interactions makes it a promising candidate for the design of new materials with applications in areas such as drug delivery, sensors, and advanced materials for energy storage and conversion.

InChI:InChI=1/C10H18O6/c1-10(2)15-7-5(4-11)14-9(13-3)6(12)8(7)16-10/h5-9,11-12H,4H2,1-3H3

Upstream product

• 3396-99-4 methyl α-D-galactopyranoside 
• 104477-41-0 Methyl 3,4-O-isopropylidene-2,6-di-O-(1-methoxy-1-methylethyl)-α-D-galactopyranoside 
• 104530-14-5 Methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-α-D-galactopyranoside 
• 77-76-9 2,2-dimethoxy-propane 
• 67-64-1 acetone 
• 116-11-0 2-Methoxypropene 
• 145933-55-7 methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-α-D-lyxo-hexopyranosyl-2-ulose 
• 5019-22-7 methyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 59-23-4 D-Galactose 

Downstream Products

• 129247-68-3 (3aS,4R,6S,7R,7aR)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 130132-27-3 (3aS,6S,7R,7aR)-6-Methoxy-2,2-dimethyl-4-(2-phenyl-benzo[1,3]dithiol-2-yloxymethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 28542-03-2 methyl 6-O-benzyl-3,4-O-isopropylidene-α-D-galactopyranoside 
• 27851-16-7 methyl 2-O-benzyl-3,4-O-isopropylidene-α-D-galactopyranoside 
• 53685-10-2 methyl 2,6-di-O-benzyl-3,4-O-isopropylidene-α-D-galactopyranoside 
• 53685-07-7 Methyl 3,4-O-isopropylidene-6-O-triphenylmethyl-α-D-galactopyranoside 
• 79526-19-5 methyl 3,4-O-isopropylidene-2,6-di-O-p-methoxybenzoyl-α-D-galactopyranoside 
• 160436-97-5 methyl 6-O-p-bromosulfonyl-3,4-O-isopropylidene-α-D-galactopyranoside 
• 114217-36-6 methyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside 
• 920741-96-4 (4S,5S)-4-((S)-1,2-Bis-benzyloxy-ethyl)-2,2-dimethyl-5-vinyl-[1,3]dioxolane 
• 53685-12-4 (3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2,4,5-triol 
• 137896-75-4 2,6-di-O-benzyl-3,4-O-isopropylidene-α/β-D-galactopyranoside 
• 93495-81-9 (2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6S)-6-((2R,3S,4R,5R,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-propoxy-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 137896-88-9 allyl O-(2,6-di-O-benzyl-3,4-isopropylidene-α-D-galactopyranosyl)-(1->4)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 

Relevant articles and documents

Stereoselective synthesis of resorcylic acid lactone Cochliomycin B

The total synthesis of 14-membered resorcylic acid lactone, Cochliomycin B has prescribed, in a convergent manner, from readily available starting materials, D-galactose, L-aspartic acid and ethyl acetoacetate. The key reactions involved in the synthesis are Julia-Kocienski olefination, E-selective Horner-Wadsworth-Emmons olefination and intramolecular lactonization.

Regioselectivity of glycosylation reactions of galactose acceptors: An experimental and theoretical study

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Localization-controlled two-color luminescence imaging: Via environmental modulation of energy transfer in a multichromophoric species

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Allylic Azide Rearrangement in Tandem with Huisgen Cycloaddition for Stereoselective Annulation: Synthesis of C-Glycosyl Iminosugars

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Linearization of carbohydrate derived polycyclic frameworks

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Lipases in the regioselective preparation of glyceric acid esters of methyl glycosides

The lipase-catalyzed regioselective acylation of methyl α-D-galacto-, -gluco- and -mannopyranosides with isopropylidene-protected (R)- and (S)-glyceric acid methyl esters in organic solvents is presented. Factors affecting the formation of the 6-O-mono- and 2,6-O-diacylated products are examined and preparative-scale reactions are detailed. In addition, studies on partially protected methyl α-D-galactopyranosides are presented, with the 3,4-O-isopropylidene protected compound leading exclusively to the formation of the 6-O-monoacylated product even at high substrate concentrations. Application of acidic resin in methanol allows removal of the isopropylidene protection groups without disturbing the ester bond at C-6. Copyright

Nano n-propylsulfonated magnetic γ-Fe 2O 3 as an efficient and reusable catalyst for the synthesis O-isopropylidene derivatives of carbohydrates

Nano n-propylsulfonated γ-Fe2O3 was found to be a highly efficient, reusable heterogeneous catalyst for the conversion of a range of monosaccharides and some of their derivatives to the corresponding O-isopropylidene derivatives in good to excellent yields by refluxing the reaction mixture in dry acetone. The magnetic property of the catalyst enabled its separation from the reaction mixture by a simple process of filtration along with the aid of an external magnet. The efficiency of the catalyst was found to be largely unaffected for at least up to six cycles of reuse, thus proving the new methodology to be environmentally rewarding besides being simple and facile in operation.

Hydroxy group acidities of partially protected glycopyranosides

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