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

• 59-23-4 D-Galactose 
• 18524-41-9 (3aR,5S,5aR,8aS,8bR)-methyl-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-carboxylate 
• 4026-28-2 1,2:3,4-di-O-isopropylidene-6-iodo-D-galactopyranose 
• 4860-78-0 6-O-acetyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 144461-52-9 1,2:3,4-di-O-isopropylidene-6-O-(2,2,6,6-tetramethyl-1-piperidinyl)-α-D-galactopyranose 
• 4478-43-7 (1,2:3,4-di-O-isopropylidene-6-O-(p-toluensulfonate))-D-galactopiranose 
• 1730-25-2 allylmagnesium bromide 
• 59401-67-1 1,2:3,4-Di-O-isopropyliden-6-O-pentaflyl-α-D-galaktopyranose 
• 2771-58-6 6-O-Allyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 80667-80-7 1,2:3,4-di-O-isopropylidene-6-O-(N-imidazole-1-sulfonyl)-α-D-galactopyranose 
• 108678-44-0 tert-butyldimethyl(2,2,7,7-tetramethyltetrahydrobis[1,3]dioxolo[5,4-b:4',5'-d]pyran-5-ylmethoxy)silane 
• 7664-93-9 sulfuric acid 
• 67-64-1 acetone 
• 10257-28-0 D-Galactose 

Downstream Products

• 99458-24-9 (2R,3S)-3-Benzoylamino-2-benzyloxymethoxy-3-phenyl-propionic acid (3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester 
• 131919-43-2 C₄₆H₄₆O₁₅ 
• 129492-27-9 1,2:3,4-bis-O-(1-methylethylidene)-6-O-(2-pyridinylmethyl)-α-D-galactopyranose 
• 1824-93-7 methyl-β-D-galactofuranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 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 
• 139378-96-4 6'-(1',2':3',4'-diisopropylidenegalactopyranosyl) 3-O-benzyl-2-deoxy-2-(phenylthio)-β-D-glucopyranoside 
• 139378-97-5 6'-(1',2':3',4'-diisopropylidenegalactopyranosyl) 3-O-benzyl-2-deoxy-2-(phenylthio)-α-D-glucopyranoside 
• 139523-60-7 6'-(1',2':3',4'-diisopropylidenegalactopyranosyl) 3-O-benzyl-2-deoxy-2-(phenylthio)-α-D-mannopyranoside 
• 124718-73-6 6'-(1',2':3',4'-diisopropylidenegalactopyranosyl) 3-O-benzyl-4,6-isopropylidene-2-deoxy-2-(phenylthio)-β-D-glucopyranoside 
• 124754-16-1 6'-(1',2':3',4'-diisopropylidenegalactopyranosyl) 3-O-benzyl-4,6-isopropylidene-2-deoxy-2-(phenylthio)-α-D-mannopyranoside 
• 161835-18-3 O-(3,5-Di-O-benzyl-α-D-lyxofuranosyl)-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 

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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Me3SI-promoted chemoselective deacetylation: a general and mild protocol

A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.

General Strategy for Integrated Bioorthogonal Prodrugs: Pt(II)-Triggered Depropargylation Enables Controllable Drug Activation in Vivo

Bioorthogonal decaging reactions for controllable drug activation within complex biological systems are highly desirable yet extremely challenging. Herein, we find a new class of Pt(II)-triggered bioorthogonal cleavage reactions in which Pt(II) but not Pt(IV) complexes effectively trigger the cleavage of O/N-propargyl in a variety of ranges of caged molecules under biocompatible conditions. Based on these findings, we propose a general strategy for integrated bioorthogonal prodrugs and accordingly design a prodrug 16, in which a Pt(IV) moiety is covalently connected with an O2-propargyl diazeniumdiolate moiety. It is found that 16 can be specifically reduced by cytoplasmic reductants in human ovarian cancer cells to liberate cisplatin, which subsequently stimulates the cleavage of O2-propargyl to release large amounts of NO in situ, thus generating synergistic and potent tumor suppression activity in vivo. Therefore, Pt(II)-triggered depropargylation and the integration concept might provide a general strategy for broad applicability of bioorthogonal cleavage chemistry in vivo.

D-galactose-based organogelator for phase-selective solvent removal and sequestration of cationic dyes

Naturally occurring sugar-based monomers are attractive substrates in the design of functional glycopolymers. In this study, we report on the development of D-galactose based organogels of varying crosslink density capable of selective adsorption of dyes and solvents. Free radical polymerization of 6-O-methacryloyl-1,2;3,4-di-O-isopropylidene-D-galactose in the presence of nonamethylene glycoldimethacrylate generated novel crosslinked polymers OG10, OG15 and OG20 with 10, 15 and 20 wt% crosslinker, respectively. Depending on the nature of the solvent, OG10 undergoes swelling upto 935%. The negative zeta potential, as determined from DLS measurements, and the gelation ability suggested the potential utility of the polymer for dye removal from water. OG10 displayed significant adsorption of rhodamine B (RhB) (>95%), crystal violet (>93%), and methylene blue (>70%) dyes as well as the selective adsorption of >90% RhB from a solution containing both RhB and methyl orange. These porous organogels are also found to be suitable for phase-selective removal of organic solvents.