Conditions | Yield |
---|---|
With Amberlite IR-120 for 2h; Heating; | 100% |
With acetyl chloride at 7 - 20℃; for 11h; | 100% |
With acetyl chloride at 40℃; for 2h; | 95% |
Conditions | Yield |
---|---|
With hydrogenchloride; acetone for 1h; | 100% |
With toluene-4-sulfonic acid In acetone | 100% |
With hydrogenchloride In acetone for 1h; | 96.7% |
1,2-dimethoxypropane
ascorbic acid
5,6-O-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dimethyl sulfoxide; acetone at 50℃; for 5h; | 95% |
Conditions | Yield |
---|---|
In acetone at 5 - 20℃; for 22.5h; Inert atmosphere; | 91% |
In potassium hydroxide; acetone | 77% |
In acetone | |
In acetone at 20℃; for 16h; | |
In acetone |
ascorbic acid
5,6-O-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
With trichlorophosphate In acetone at 20℃; for 4h; | 89% |
With copper(II) sulfate; acetone | |
In acetone |
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane |
3,5-O-benzylidene-6-O-t-butyldimethylsilyl-L-xylo-hex-2-ulosonic acid 1,4-lactone 2-hydrate
5,6-O-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq. HOAc / 4 h / 80 °C 2: AcCl / 2 h / 18 °C View Scheme |
Conditions | Yield |
---|---|
In ethyl acetate; acetone |
ascorbic acid
B
5,6-O-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
In acetone |
Conditions | Yield |
---|---|
With acetyl chloride at 40℃; for 3h; |
dimethyl sulfate
5,6-O-isopropylidene-L-ascorbic acid
2,3-O-bis-methyl-5,6-O-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 3h; Heating; | 100% |
With potassium carbonate In acetone Heating; | 96% |
With potassium carbonate In acetone for 3h; Heating; Yield given; |
chloromethyl methyl ether
5,6-O-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating; | 98% |
tert-butyldimethylsilyl chloride
5,6-O-isopropylidene-L-ascorbic acid
(2R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2H-furan-5-one
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 14.5h; | 98% |
1-methyl-1-nitrosourea
5,6-O-isopropylidene-L-ascorbic acid
5,6-O-isopropylidene-3-O-methyl-L-ascorbic acid
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at -20℃; | 97% |
5,6-O-isopropylidene-L-ascorbic acid
(2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanoic acid
Conditions | Yield |
---|---|
With water; dihydrogen peroxide; potassium carbonate at 20℃; for 24h; | 96% |
With palladium 10% on activated carbon; dihydrogen peroxide; calcium carbonate In water at 20 - 40℃; | 89% |
With dihydrogen peroxide; calcium carbonate |
1-Bromoheptane
5,6-O-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at -10 - 20℃; | 96% |
ethyl bromide
5,6-O-isopropylidene-L-ascorbic acid
(R)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-ethoxy-3-hydroxyfuran-2(5H)-one
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; for 3h; not specified; | 95% |
With anion exchange resin with multi-iodide anions In N,N-dimethyl-formamide at 20℃; | 95% |
With sodium hydrogencarbonate In dimethyl sulfoxide at 50℃; for 16h; | 70% |
Stage #1: 5,6-O-isopropylidene-L-ascorbic acid With sodium hydrogencarbonate In dimethyl sulfoxide at 20℃; for 0.333333h; Stage #2: ethyl bromide In dimethyl sulfoxide at 50℃; for 17h; | 62% |
With sodium hydrogencarbonate In dimethyl sulfoxide at 70℃; for 2h; Reagent/catalyst; Temperature; Solvent; | 16.2 g |
pivaloyl chloride
5,6-O-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
Stage #1: pivaloyl chloride With 1H-imidazole In dichloromethane at 20℃; for 1h; Stage #2: 5,6-O-isopropylidene-L-ascorbic acid In dichloromethane at 20℃; | 95% |
5,6-O-isopropylidene-L-ascorbic acid
2,3-O-bis-methyl-5,6-O-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; potassium hydroxide In water; ethyl acetate at 20℃; for 24h; | 94% |
5,6-O-isopropylidene-L-ascorbic acid
calcium bis[(2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)acetate]
Conditions | Yield |
---|---|
With dihydrogen peroxide; calcium carbonate In water at 20 - 50℃; for 4h; | 92% |
With dihydrogen peroxide; calcium carbonate In water at 30 - 40℃; for 0.5h; | 78% |
With dihydrogen peroxide; calcium carbonate In water at 40℃; Ice-bath cooling; | |
With dihydrogen peroxide; calcium carbonate In water at 25 - 60℃; for 7h; | 55 mg |
Thioctic acid
5,6-O-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
With pyridine; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 92% |
5,6-O-isopropylidene-L-ascorbic acid
methyl iodide
5,6-O-isopropylidene-3-O-methyl-L-ascorbic acid
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran; dimethyl sulfoxide Ambient temperature; 1.) 20 min, 2.) 6 h; | 91% |
With potassium carbonate In tetrahydrofuran; dimethyl sulfoxide at 20℃; | 91% |
With cesium fluoride In dimethyl sulfoxide at 20℃; | 61% |
5,6-O-isopropylidene-L-ascorbic acid
methyl iodide
5,6-O-isopropylidene-2-O-methyl-L-ascorbic acid
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at -10 - 20℃; | 91% |
5,6-O-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
Stage #1: 5,6-O-isopropylidene-L-ascorbic acid With calcium carbonate In water at 0℃; for 1h; Stage #2: With dihydrogen peroxide In water at 0 - 10℃; Stage #3: With catalase In water at 20℃; for 2h; Product distribution / selectivity; | 91% |
Stage #1: 5,6-O-isopropylidene-L-ascorbic acid With calcium carbonate In water at 0℃; for 1.25h; Stage #2: With dihydrogen peroxide In water at 0 - 20℃; for 6h; Stage #3: With catalase In water Product distribution / selectivity; | 89.4% |
Stage #1: 5,6-O-isopropylidene-L-ascorbic acid With calcium carbonate In water at 0℃; for 0.5h; Stage #2: With dihydrogen peroxide In water at 0 - 20℃; Stage #3: palladium on carbon; pyrographite In water at 50℃; for 0.5h; Product distribution / selectivity; | 77% |
Stage #1: 5,6-O-isopropylidene-L-ascorbic acid With calcium carbonate In water at 0℃; for 0.5h; Stage #2: With dihydrogen peroxide In water Stage #3: palladium on carbon; pyrographite In water at 50℃; for 0.5h; Product distribution / selectivity; |
acetyl chloride
5,6-O-isopropylidene-L-ascorbic acid
[(2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-5-oxo-2H-furan-4-yl] acetate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 2h; | 90% |
With pyridine In dichloromethane Cooling with ice; | 76.1% |
With pyridine In dichloromethane Cooling with ice; | 76.1% |
With pyridine |
diethyl sulfate
5,6-O-isopropylidene-L-ascorbic acid
(R)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-ethoxy-3-hydroxyfuran-2(5H)-one
Conditions | Yield |
---|---|
With triethylamine In ethanol for 2h; Reflux; | 87.9% |
With potassium hydroxide In dimethyl sulfoxide at 80℃; for 2h; | 16.5 g |
5,6-O-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
With sodium hypochlorite; ruthenium(IV) oxide In sodium hydroxide at 55 - 60℃; for 0.666667h; pH 8.0; | 87% |
Multi-step reaction with 2 steps 1: aq. H2O2, CaCO3 2: 95 percent / aq. NaOCl, RuCl3, NaOH / 0.5 h / Ambient temperature View Scheme |
Cinnamyl bromide
5,6-O-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at -10 - 20℃; | 87% |
5,6-O-isopropylidene-L-ascorbic acid
(2S,3S)-1,2-O-isopropylidene-1,2,3,4-tetrol
Conditions | Yield |
---|---|
Stage #1: 5,6-O-isopropylidene-L-ascorbic acid With dihydrogen peroxide; potassium carbonate In water at 20℃; Inert atmosphere; Stage #2: With ethyl iodide In acetonitrile Inert atmosphere; Reflux; Stage #3: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; Inert atmosphere; | 87% |
Multi-step reaction with 3 steps 1: H2O2; K2CO3 / H2O 2: 93 percent / acetonitrile / 82 °C 3: 96 percent / BH3-SMe2; NaBH4 View Scheme | |
Multi-step reaction with 2 steps 1: 1.) CuSO4, 2.) K2CO3, H2O2, 3.) KI 2: LiAlH4 / tetrahydrofuran View Scheme |
benzyl bromide
5,6-O-isopropylidene-L-ascorbic acid
O3-benzyl-O5,O6-(1-methylethylidene)-L-ascorbic acid
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran; dimethyl sulfoxide at 20℃; | 86% |
With cesium fluoride In dimethyl sulfoxide at 20℃; | 62% |
With sodium carbonate In acetone for 4h; Reflux; | 61.8% |
Conditions | Yield |
---|---|
Stage #1: 5,6-O-isopropylidene-L-ascorbic acid With dmap In dichloromethane at 20℃; for 0.25h; Alkaline conditions; Stage #2: C41H67NO5S In dichloromethane for 0.333333h; Alkaline conditions; | 85.1% |
acetyl chloride
5,6-O-isopropylidene-L-ascorbic acid
5,6-O-Isopropylidene-3-O-acetyl-L-ascorbic acid
Conditions | Yield |
---|---|
With pyridine In dichloromethane Ambient temperature; 1.) 20 min, 2.) 2 h; | 85% |
With triethylamine In acetone at 25℃; for 0.0333333h; further reagents and conditions; | 61 % Spectr. |
diethyl sulfate
5,6-O-isopropylidene-L-ascorbic acid
3-o-ethyl-5,6-o-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethanol at 55℃; for 7h; | 83.4% |
benzyl bromide
5,6-O-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at -10 - 20℃; | 83% |
5,6-O-isopropylidene-L-ascorbic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide; calcium carbonate In water for 3h; Ambient temperature; | 81% |
The CAS registry number of L-Ascorbicacid, 5,6-O-(1-methylethylidene)- is 15042-01-0. The systematic name is 5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxyfuran-2(5H)-one. In addition, the molecular formula is C9H12O6 and the molecular weight is 216.19. It is a kind of white powder and belongs to the classes of Vitamins and Derivatives; 13C & 2H Sugars; Biochemistry; O-Substituted Sugars; Sugar Acids; Sugars; Vitamin Derivatives; Vitamins; Carbohydrates & Derivatives.
Physical properties about this chemical are: (1)ACD/LogP: -1.33; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1; (4)ACD/LogD (pH 7.4): -3; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 85.22 Å2; (13)Index of Refraction: 1.58; (14)Molar Refractivity: 47.37 cm3; (15)Molar Volume: 142.376 cm3; (16)Surface Tension: 64.818 dyne/cm; (17)Density: 1.518 g/cm3; (18)Flash Point: 160.964 °C; (19)Enthalpy of Vaporization: 74.608 kJ/mol; (20)Boiling Point: 395.216 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25 °C; (22)Polarizability: 18.779 ×10-24cm3.
Preparation of L-Ascorbicacid, 5,6-O-(1-methylethylidene)- :this chemical can be prepared by 3-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-5,10-dihydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one. This reaction will need reagent H2, catalyst Pd(OH)2 on C and solvent ethanol. The yield is about 80% with reaction pressure of 760 Pa.
Uses of L-Ascorbicacid, 5,6-O-(1-methylethylidene)-: it can react with 1,2-bis-bromomethyl-benzene to produce 3-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-5,10-dihydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one. This reaction will need reagent sodium hydride and solvent tetrahydrofuran. The reaction time is 30 minutes with ambient temperature. The yield is about 62%.
When you are using this chemical, please be cautious about it as the following:
During using it, you should avoid contact with skin and eyes. In addition, you should not breathe dust.
You can still convert the following datas into molecular structure:
(1) SMILES: O\C2=C(/O)C(=O)O[C@@H]2[C@H]1OC(C)(C)OC1
(2) InChI: InChI=1/C9H12O6/c1-9(2)13-3-4(15-9)7-5(10)6(11)8(12)14-7/h4,7,10-11H,3H2,1-2H3/t4-,7+/m0/s1
(3) InChIKey: POXUQBFHDHCZAD-MHTLYPKNBS
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