Conditions | Yield |
---|---|
With acetyl chloride for 0.583333h; Heating; microwave irradiation; | 100% |
Amberlite IR-120 (H+) resin for 24h; Heating; | 55% |
With hydrogenchloride | |
With Amberlite IR 120 (H+ form) for 0.333333h; Reflux; Microwave irradiation; | |
With acetyl chloride for 12h; Inert atmosphere; Reflux; |
methyl 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranoside
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen In methanol; ethyl acetate for 3h; Molecular sieve; | 100% |
Conditions | Yield |
---|---|
With polymer-supported potassium thiophenolate In tetrahydrofuran; methanol at 80℃; for 2.5h; | 98% |
With Amberlyst A-26(OH) In methanol for 6h; Ambient temperature; | 94% |
methyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With tris(2,4,6-trimethoxyphenyl)phosphine In methanol at 20℃; for 30h; | 93% |
In methanol; water; triethylamine at 20℃; for 24h; | |
With methanol; sodium methylate at 20℃; Reagent/catalyst; | 100 %Spectr. |
With ammonium hydroxide In tetrahydrofuran; methanol |
Conditions | Yield |
---|---|
tetrafluoroboric acid In acetonitrile at 20℃; for 0.2h; | 87.2% |
methyl α-galactopyranoside 6-sulfate
A
methyl 2,3-dideoxy-α-D-threo-hexopyranoside
B
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With sodium hydroxide at 100℃; | A 86% B n/a |
With sodium hydroxide at 100℃; Title compound not separated from byproducts; | A 86% B n/a |
methanol
D-Galactose
A
Methyl α,β-D-galactofuranoside
B
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With iron(III) chloride Heating; | A 65% B 24% |
methanol
D-Galactose
A
methyl α-D-galactofuranoside
B
methyl-β-D-galactofuranoside
C
methyl beta-D-galactopyranoside
D
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With amberlite IR-120H In methanol at 35℃; for 48h; | A 17 % Spectr. B 60% C 6 % Spectr. D 9 % Spectr. |
D-Galactose
A
methyl beta-D-galactopyranoside
B
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With hydrogenchloride; methanol |
Conditions | Yield |
---|---|
With hydrogenchloride; methanol; dimethylsulfite |
D-Galactose-dibenzyldithioacetal
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With methanol; mercury dichloride |
methanol
D-Galactose
A
methyl beta-D-galactopyranoside
B
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With hydrogenchloride for 16h; Heating; |
methanol
C50H83NO21
A
C27H43NO2
B
methyl-α-D-xylopyranoside
C
methyl-alpha-D-glucopyranoside
D
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With hydrogenchloride for 2h; Heating; characterization by hydrolysis products; |
methanol
C50H81NO21
B
methyl-α-D-xylopyranoside
C
methyl-alpha-D-glucopyranoside
D
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With hydrogenchloride for 2h; Heating; characterization by hydrolysis products; |
Conditions | Yield |
---|---|
With hydrogenchloride; potassium hydroxide for 1h; Heating; Title compound not separated from byproducts; | |
With hydrogenchloride; potassium hydroxide for 1h; Product distribution; Heating; |
1-O-methyl-4-keto-α-D-glucopyranoside
A
methyl-alpha-D-glucopyranoside
B
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol | |
With sodium tetrahydroborate In methanol for 1h; Product distribution; Ambient temperature; |
methyl α-D-lyxo-hexopyranosid-4-ulose
A
(+)-Methyl-α-D-talopyranosid
B
methyl-alpha-D-glucopyranoside
C
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol Title compound not separated from byproducts; |
C28H25O8(1+)
A
methyl beta-D-galactopyranoside
B
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With sodium methylate In methanol Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
methanol
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
A
methyl-β-D-galactofuranoside
B
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With iodine for 4h; Heating; Yield given. Yields of byproduct given; |
sodium methylate
A
1,6-anhydro-β-D-galactopyranose
B
methyl beta-D-galactopyranoside
C
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
In pyridine; methanol at 80℃; for 2.5h; |
A
1,6-anhydro-β-D-galactopyranose
B
methyl beta-D-galactopyranoside
C
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With sodium methylate In pyridine; methanol at 80℃; for 2.5h; |
Conditions | Yield |
---|---|
With hydrogenchloride Product distribution; |
methanol
methyl 1-thio-β-D-galactopyranoside
A
methyl beta-D-galactopyranoside
B
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With iodine at 18 - 20℃; for 2h; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With α-D-galactosidase from Trichoderma reesei In water at 37℃; Rate constant; NaOAc buffer, pH 5.6; |
1,4-dioxane
methyl α-galactopyranoside 6-sulfate
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
Erhizten des Barium-Salzes; |
A
methyl α-D-galactopyranoside
B
3,6-Anhydro-D-galactose-dimethylacetal
C
Carrabiose-dimethylacetal
Conditions | Yield |
---|---|
methanolysis; | A 0.47 g B 0.16 g C 0.77 g |
hydrogenchloride
methanol
dimethylsulfite
D-Galactose
A
methyl beta-D-galactopyranoside
B
methyl α-D-galactopyranoside
(2R,3R,4S,5R,6S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-methoxy-tetrahydro-pyran-3,4,5-triol
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With pyridine; ammonium cerium(IV) nitrate In acetone at 68℃; for 4h; pH=4.4; | 94 % Chromat. |
Ectyoceramide
A
methyl beta-D-galactopyranoside
B
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 80℃; for 12h; |
benzaldehyde dimethyl acetal
methyl α-D-galactopyranoside
methyl 4,6-O-benzylidene-α-D-galactopyranoside
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid In chloroform at 65℃; | 100% |
With tetrafluoroboric acid In diethyl ether; N,N-dimethyl-formamide at 20℃; for 16h; | 96% |
With toluene-4-sulfonic acid; 1-butyl-3-methylimidazolium Tetrafluoroborate at 80℃; for 2h; | 92% |
triisopropylsilyl chloride
methyl α-D-galactopyranoside
Conditions | Yield |
---|---|
Stage #1: triisopropylsilyl chloride; methyl α-D-galactopyranoside With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Stage #2: benzoyl haloide | 100% |
9-anthracenecarboxaldehyde dimethyl acetal
methyl α-D-galactopyranoside
(2S,4aR,6S,7R,8R,8aR)-2-(anthracen-9-yl)-6-methoxyhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In acetonitrile at 20℃; for 16h; | 100% |
benzyl bromide
methyl α-D-galactopyranoside
2,3,4-tri-O-benzyl-D-galactopyranoside
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 17h; Inert atmosphere; | 100% |
vinyl acetate
methyl α-D-galactopyranoside
((2R,3R,4S,5R,6S)-5-acetoxy-3,4-dihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl acetate
Conditions | Yield |
---|---|
With immobilized Novozym 435 from Candida antarctica lipase B In tetrahydrofuran at 45℃; for 51h; Enzymatic reaction; regioselective reaction; | 100% |
acetic anhydride
methyl α-D-galactopyranoside
methyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside
Conditions | Yield |
---|---|
With iodine at 20℃; for 0.15h; | 99% |
With lithium perchlorate for 30h; Heating; | 99% |
With iodine at 20℃; for 0.0833333h; Acetylation; | 98% |
methyl α-D-galactopyranoside
methyl iodide
(2S,3R,4S,5S,6R)-2,3,4,5-Tetramethoxy-6-methoxymethyl-tetrahydro-pyran
Conditions | Yield |
---|---|
Stage #1: methyl α-D-galactopyranoside With sodium hydride In N,N-dimethyl-formamide; paraffin oil at 0℃; for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide; paraffin oil at 0 - 20℃; for 24h; | 99% |
Stage #1: methyl α-D-galactopyranoside With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 4h; Inert atmosphere; | 82% |
With potassium fluoride on basic alumina In acetonitrile | 80% |
3,5-bis(trifluoromethyl)benzenesulfonyl chloride
methyl α-D-galactopyranoside
methyl 3-O-[3,5-bis(trifluoromethyl)benzenesulfonyl]-α-D-galactopyranoside
Conditions | Yield |
---|---|
Stage #1: methyl α-D-galactopyranoside With dibutyltin chloride In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 3,5-bis(trifluoromethyl)benzenesulfonyl chloride With 1,2,2,6,6-pentamethylpiperidine In tetrahydrofuran at 10℃; for 12h; regioselective reaction; | 99% |
benzoyl chloride
methyl-alpha-D-glucopyranoside
methyl α-D-galactopyranoside
A
methyl O3-benzoyl-α-D-galactoside
B
methyl O2-benzoyl-α-D-glucoside
Conditions | Yield |
---|---|
Stage #1: methyl-alpha-D-glucopyranoside; methyl α-D-galactopyranoside With dibutyltin chloride In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: benzoyl chloride With 1,2,2,6,6-pentamethylpiperidine; tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 20℃; chemoselective reaction; | A 99% B 19% |
p-Anisaldehyde dimethyl acetal
methyl α-D-galactopyranoside
(2S,4aR,7R,8R,8aR)-6-methoxy-2-(4-methoxyphenyl)hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In N,N-dimethyl-formamide at 80℃; | 98% |
With 3,4-bis((3,5-bis(trifluoromethyl)phenyl)amino)cyclobut-3-ene-1,2-dione In acetonitrile at 20℃; for 14h; Inert atmosphere; | 82% |
With (1S)-10-camphorsulfonic acid In acetonitrile at 50℃; under 225.023 Torr; for 2.5h; Inert atmosphere; |
3,5-difluorobenzenesulfonyl chloride
methyl α-D-galactopyranoside
methyl 3-O-(3,5-difluorobenzensulfonyl)-α-D-galactopyranoside
Conditions | Yield |
---|---|
Stage #1: methyl α-D-galactopyranoside With dibutyltin chloride In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 3,5-difluorobenzenesulfonyl chloride With 1,2,2,6,6-pentamethylpiperidine In tetrahydrofuran at 10℃; for 12h; regioselective reaction; | 98% |
benzyl bromide
methyl α-D-galactopyranoside
methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside
Conditions | Yield |
---|---|
Stage #1: methyl α-D-galactopyranoside With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; | 97% |
Stage #1: methyl α-D-galactopyranoside With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere; | 96% |
Stage #1: methyl α-D-galactopyranoside With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; | 95% |
acetone
methyl α-D-galactopyranoside
methyl 3,4-O-isopropylidene-α-D-galactopyranoside
Conditions | Yield |
---|---|
With nano n-propylsulfonated magnetic γ-Fe2O3 for 1.5h; Reflux; | 97% |
vanadyl triflate In acetonitrile at 20℃; for 11h; | 80% |
With iodine at 20℃; for 4h; | 70% |
benzyl chloride
methyl α-D-galactopyranoside
methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside
Conditions | Yield |
---|---|
Stage #1: methyl α-D-galactopyranoside In toluene at 90 - 95℃; Stage #2: benzyl chloride With sodium hydride In toluene; paraffin oil at 35 - 95℃; | 96.5% |
With sodium hydride at 130℃; | 78% |
With potassium hydroxide Etherification; alkylation; |
benzaldehyde dimethyl acetal
methyl α-D-galactopyranoside
methyl 4,6-O-benzylidene-α-D-galactopyranoside
Conditions | Yield |
---|---|
tetrafluoroboric acid In N,N-dimethyl-formamide at 20℃; for 4h; | 96.4% |
With sulfuric acid In methanol Heating; | 96% |
With camphor-10-sulfonic acid In acetonitrile at 20℃; for 15h; pH=3; | 50% |
2-bromomethylnaphthyl bromide
methyl α-D-galactopyranoside
methyl 3-O-NAP-α-D-galactoside
Conditions | Yield |
---|---|
Stage #1: methyl α-D-galactopyranoside With di(n-butyl)tin oxide In benzene for 4h; Reflux; Stage #2: 2-bromomethylnaphthyl bromide With tetra-(n-butyl)ammonium iodide In benzene at 80 - 85℃; for 18h; | 96% |
Stage #1: methyl α-D-galactopyranoside With di(n-butyl)tin oxide In benzene for 4h; Metallation; Heating; Stage #2: 2-bromomethylnaphthyl bromide With tetra-(n-butyl)ammonium iodide at 80 - 85℃; for 18h; Alkylation; | 93% |
allyl ethyl carbonate
methyl α-D-galactopyranoside
methyl 2,3,4,6-tetra-O-allyl-α-D-galactopyranoside
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 65℃; for 12h; | 95% |
p-toluenesulfonyl chloride
methyl α-D-galactopyranoside
methyl 2,3,6-tri-O-p-tolylsulfonyl-α-D-galactopyranoside
Conditions | Yield |
---|---|
With pyridine at 25℃; for 20h; | 95% |
Conditions | Yield |
---|---|
Stage #1: C16H11F13O With toluene-4-sulfonic acid; sodium sulfate; trimethyl orthoformate In acetonitrile at 20℃; Stage #2: methyl α-D-galactopyranoside In acetonitrile Further stages.; | 95% |
1,1,1,3,3,3-hexamethyl-disilazane
methyl α-D-galactopyranoside
methyl 2,3,4,6-tetra-O-trimethylsilyl-α-D-galactopyranoside
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.333333h; Inert atmosphere; | 95% |
tert-butylchlorodiphenylsilane
methyl α-D-galactopyranoside
methyl 6-O-(tert-butyldiphenylsilyl)-α-D-galactopyranoside
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 24h; | 94% |
With 1H-imidazole In N,N-dimethyl-formamide for 5h; Inert atmosphere; | 92% |
With 1H-imidazole | 79% |
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature; | 76% |
With pyridine Ambient temperature; |
methyl α-D-galactopyranoside
1-O-methyl-4-keto-α-D-glucopyranoside
Conditions | Yield |
---|---|
With phenyltrimethylammonium tribromide; potassium carbonate In tetrahydrofuran; methanol at 20℃; for 4h; Reagent/catalyst; regioselective reaction; | 94% |
With 3 A molecular sieve; bromine; bis(tri-n-butyltin)oxide 1) CHCl3, reflux, 3 h, 2) CHCl3, 0 deg C, 8 min; Yield given. Multistep reaction; |
1,1-dimethoxy-1-(4-methoxyphenyl)ethane
methyl α-D-galactopyranoside
methyl 4,6-O-<(4-methoxyphenyl)ethylidene>-α-D-galactopyranoside
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 3h; Ambient temperature; | 93% |
(diethoxymethyl)benzene
methyl α-D-galactopyranoside
methyl 4,6-O-benzylidene-α-D-galactopyranoside
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid In chloroform Heating; | 92% |
With camphorsulfonic acid In chloroform Heating; | 92% |
With camphor-10-sulfonic acid In chloroform for 2h; Heating; |
Conditions | Yield |
---|---|
With trichlorophosphate at 65℃; for 0.5h; | 92% |
With thionyl chloride at 65℃; for 0.5h; | 83% |
tert-butyldimethylsilyl chloride
methyl α-D-galactopyranoside
6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-galactopyranoside
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 19h; | 92% |
With triethylamine; N,N-dimethyl-formamide In acetonitrile at 20℃; for 0.5h; regioselective reaction; | 89% |
With pyridine; dmap at 0 - 20℃; | 81% |
IUPAC name: (2R,3R,4S,5R,6S)-2-(Hydroxymethyl)-6-methoxyoxane-3,4,5-triol
Molecular Formula: C7H14O6
Molecular Weight: 194.18 g/mol
EINECS: 222-251-7
Storage temp.: 2-8 °C
Melting point: 116-117 °C
Index of Refraction: 1.548
Surface Tension: 68.3 dyne/cm
Density: 1.47 g/cm3
Flash Point: 189.1 °C
Appearance: White Powder
Enthalpy of Vaporization: 73.83 kJ/mol
Boiling Point: 389.1 °C at 760 mmHg
Vapour Pressure: 1.15E-07 mmHg at 25 °C
Product Categories: Sugars, Carbohydrates & Glucosides;Sugars;Galactose;13C & 2H Sugars;Biochemistry;
Carbohydrates & Derivatives;Glycosides
Following is the structure of Methyl alpha-D-galactopyranoside (CAS NO.3396-99-4):
Methyl alpha-D-galactopyranoside (CAS NO.3396-99-4) hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. And the toxicological properties have not been fully investigated.
Safety Statements: 24/25-22
S24/25:Avoid contact with skin and eyes.
S22:Do not breathe dust.
WGK Germany: 3
F: 3-10
Methyl alpha-D-galactopyranoside , its cas register number is 3396-99-4. It also can be called hexopyranoside, methyl ; and Methyl hexopyranoside . It is stable. But it incompatible with strong oxidizing agents. Methyl alpha-D-galactopyranoside (CAS NO.3396-99-4) should avoid the condition like incompatible materials and light. Its hazardous decomposition products are carbon monoxide, carbon dioxide. Its hazardous polymerization will not occur.
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