4064-06-6

Basic information

• Product Name: 1,2:3,4-Di-O-isopropylidene-D-galactopyranose
• Synonyms: DIACETONE-D-GALACTOSE;DIACETONE-ALPHA-D-GAL;1,2:3,4-DIISOPROPYLIDEN-ALPHA-D-GALACTOPYRANOSE;1,2,3,4-DI-O-ISOPROPYLIDENE-D-GALACTOPYRANOSE;1,2:3,4-DI-O-ISOPROPYLIDENE-D-GALACTOPYRANOSE;1,2:3,4-DI-O-ISOPROPYLIDENE-A-D-GALACTOPYRANOSE;1,2,3,4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTOPYRANOSE;1,2:3,4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTOPYRANOSE
• CAS NO: 4064-06-6
• Molecular Formula: C₁₂H₂₀O₆
• Molecular Weight: 260.28
• EINECS: 223-771-7
• Product Categories: Sugars, Carbohydrates & Glucosides;13C & 2H Sugars;Biochemistry;Galactose;O-Substituted Sugars;Sugars;Carbohydrates & Derivatives;carbohydrate
• Mol File: 4064-06-6.mol
• Article Data: 171

Chemical Properties

• Melting Point: 120-122 °C
• Boiling Point: 117 °C0.015 mm Hg(lit.)
• Flash Point: 159.3 °C
• Appearance: Clear pale yellow to yellow/Viscous Paste
• Density: 1.143 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.17E-07mmHg at 25°C
• Refractive Index: n20/D 1.466(lit.)
• Storage Temp.: 2-8°C
• Solubility: Soluble in Acetone, Chloroform and Methanol.
• PKA: 14.00±0.10(Predicted)
• BRN: 1345410
• CAS DataBase Reference: 1,2:3,4-Di-O-isopropylidene-D-galactopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:3,4-Di-O-isopropylidene-D-galactopyranose(4064-06-6)
• EPA Substance Registry System: 1,2:3,4-Di-O-isopropylidene-D-galactopyranose(4064-06-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37-26
• WGK Germany: 3
• F: 3-9-21
• Hazardous Substances Data: 4064-06-6(Hazardous Substances Data)

Usage

Chemical Properties

Thick Yellow Oil

Uses

Diacetone-D-galactose is used to produce diacetone-d-galacturonic acid and oxalic acid. It is mainly used in biochemical reaction and used as medicine intermediate.

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

Upstream product

• 85597-20-2 1,3-Diphenyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-[1,3,2]diazaphospholidine 
• 108678-44-0 tert-butyldimethyl(2,2,7,7-tetramethyltetrahydrobis[1,3]dioxolo[5,4-b:4',5'-d]pyran-5-ylmethoxy)silane 
• 59-23-4 D-Galactose 
• 7664-93-9 sulfuric acid 
• 67-64-1 acetone 
• 10257-28-0 D-Galactose 
• 116-11-0 2-Methoxypropene 
• 1990-29-0 D-altrose 
• 25253-46-7 (3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carboxylic acid 
• 70932-48-8 (3aS,5R,5aS,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-carbaldehyde 
• 350498-59-8 1,2,3,4-di-O-isopropylidene-D-galactopyranosyl 7-methoxycoumarin-4-ylmethoxycarbonate 
• 218937-73-6 5-(4-methoxybenzyloxymethyl)-2,2,7,7-tetramethyl-(3aR,5R,5aS,8aS,8bR)-perhydrodi-1,3-dioxolo[4,5-b:4',5'-d]pyran 
• 350498-58-7 1,2,3,4-di-O-isopropylidene-D-galactopyranosyl pyren-1-ylmethoxycarbonate 
• 350498-57-6 1,2,3,4-di-O-isopropylidene-D-galactopyranosyl anthraquinon-2-ylmethoxycarbonate 

Downstream Products

• 64842-82-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-[1:2,3:4]-di-O-isopropylidene-α-D-galactopyranoside 
• 41671-29-8 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 177536-77-5 Cyclohexyl-carbamic acid (2R,3aS,4S,6R,7R,7aS)-4-methyl-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-2-trichloromethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 
• 70751-54-1 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-1,2,5,6-bis(di-O-isopropylidene)-α-D-galactopyranoside 
• 4711-00-6 6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-D-galactopyranose 
• 38838-08-3 6-bromo-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 65342-54-3 6-O-formyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 4933-77-1 (3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde 
• 20581-67-3 1,2:3,4-di-O-isopropylidene-6-O-(methylthio)methyl-α-D-galactopyranose 
• 34698-17-4 O¹,O²;O³,O⁴-diisopropylidene-O⁶-methyl-α-D-galactopyranose 
• 5239-08-7 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-O-diisopropylidene-α-D-galactopyranose 
• 4860-78-0 6-O-acetyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 35437-38-8 O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosyl)-β-(1<*>6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 

Relevant articles and documents

Reductive Cleavage of Sulfonates. Deprotection of Carbohydrate Tosylates by Photoinduced Electron Transfer

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Rapid synthesis of 1-deoxygalactonojirimycin using a carbamate annulation

A remarkably efficient synthesis of the biologically important iminosugar 1-deoxygalactonojirimycin (DGJ) is presented. Key to this strategy is the development of a novel carbamate annulation reaction that favours formation of a six-membered carbamate-containing piperidine skeleton over its five-membered counterpart.

Ready preparation of sugar acetals under ultrasonic irradiation

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Thermoresponsive copolymers with pendant d-galactosyl 1,2,3-triazole groups: Synthesis, characterization and thermal behavior

A galactose containing glycomonomer has been synthesized by copper catalyzed azide-alkyne cyclo-addition reaction (CuAAC) of 6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-α-d-galactopyranose with propargyl acrylate. This monomer was subjected to homopolymerization and copolymerization with N-isopropylacrylamide (NIPAm) at different compositions by free radical polymerization using 2,2′-azobis-isobutyronitrile (AIBN) as an initiator. The composition of the copolymer was determined by 1H-NMR spectroscopy. Upon acid hydrolysis of acetonide protected polymers, water-soluble deprotected polymers were obtained. The polymers were characterized and confirmed by NMR, IR, GPC and thermal analytical techniques. The protected and deprotected copolymers showed a sharp cloud-point temperature and a linear correlation was obtained between the lower critical solution temperatures (LCST) and the concentration of glycomonomer in the copolymers. This allows tuning the thermal response by simply altering the copolymer composition. Water contact angle experiments showed the changes in the hydrophilicity of copolymers with compositions that supported the LCST results. The glass transition temperature of protected copolymers followed a regular monotonic decreasing trend with increasing glycomonomer content, whereas Tg of deprotected copolymers increased due to H-bond interaction. The attempts to develop thermoresponsive polymers having LCSTs at physiological temperature were successful.

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Synthesis, spectroscopic studies, and x-ray crystallographic analysis of the organotin carbohydrate: 1,2:3,4-di-O-isopropylidene-6-O-triphenylstannylmethyl-α-D-galactopyranose

The title organotin carbohydrate, C31H36O6Sn, has been synthesized and its molecular structure has been determined in solution and in the solid state.NMR, infrared, mass and X-ray crystallographic techniques were used.The chiral molecules crystallize in the monoclinic space group P21 with Z=2.The triphenyltin and carbohydrate moieties are linked by a trans methylene-oxygen-methylene arrangement.The pyranosyl ring adopts a twist-boat conformation and the isopropylidene rings adopt different (half-chair and envelope) forms.Solution and solid-state conformations are similar as only three Δ 13C shift values are greater than 2ppm; the Δ 119Sn value is 12 ppm.KEY WORDS: X-ray crystallographic analysis; organotin; carbohydrate.

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Epoc group: Transformable protecting group with gold(iii)-catalyzed fluorene formation

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Synthesis and applications of carbohydrate based chiral ionic liquids as chiral recognition agents and organocatalysts

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Asymmetric total syntheses of naturally occurring α,β-enone-containing RALs, L-783290 and L-783277 through intramolecular base-mediated macrolactonization reaction

Asymmetric total synthesis of two naturally occurring α,β-enone containing RALs, L-783290 and L-783277 is described in this article. An E-selective Horner-Wadsworth-Emmons (HWE) olefination was used as a key reaction to construct the C7′-C8′ olefinic unsaturation in L-783290. An enantiopure alkyne addition to the aldehyde followed by Z-selective partial reduction was employed to construct the C7′-C8′ olefinic unsaturation in L-783277. Biomimetic lactonization reaction was used to construct the macrolactone core in both the target molecules.