(2S,3R,4S)-5,5-Diethoxy-pentane-1,2,3,4-tetraol
L-xylose
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran | 95% |
Tetra-O-acetyl-aldehydo-L-xylose
L-xylose
Conditions | Yield |
---|---|
With sodium ethanolate at 20 - 30℃; | 92% |
Conditions | Yield |
---|---|
With molybdenum(VI) oxide In water at 90℃; for 9h; Bilik reaction; | A n/a B n/a C 19% |
(2S,3S,4R)-5-hexene-1,2,3,4-tetrol
L-xylose
Conditions | Yield |
---|---|
With ozone; sodium sulfite 1.) MeOH, -78 deg C, 2. a) -78 deg C, 1 h, b) r.t., 15 h; Yield given. Multistep reaction; |
3,4,5,6-tetra-O-acetyl-1,2-dideoxy-L-xylo-hex-1-enitol
L-xylose
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
water
ascorbic acid
A
furfural
B
L-xylose
C
carbon dioxide
L-xylose
Conditions | Yield |
---|---|
With lead(IV) acetate; acetic acid anschliessendes Erwaermen mit wss.Schwefelsaeure; | |
With lead(II,IV) oxide; acetic acid anschliessendes Behandeln mit wss.Schwefelsaeure,zuletz bei 100grad; | |
With sodium periodate anschliessendes Behandeln mit wss.Saeure; |
L-xylose
Conditions | Yield |
---|---|
With lead(IV) acetate; acetic acid Erwaermen des Reaktionsprodukts mit wss.Essigsaeure; | |
With water; periodic acid Erwaermen des Reaktionsprodukts mit Essigsaeure; |
L-xylose
Conditions | Yield |
---|---|
With lead(IV) acetate; ammonium hydroxide; acetic acid anschliessendes Erhitzen; |
(S)-cyclohexylidene glyceraldehyde
A
L-xylose
B
L-lyxose
C
L-ribose
D
L-arabinose
Conditions | Yield |
---|---|
In dichloromethane Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
In dichloromethane Ambient temperature; Yield given. Yields of byproduct given; |
(S)-cyclohexylidene glyceraldehyde
A
L-xylose
B
L-lyxose
C
L-ribose
D
L-arabinose
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given; |
D-sorbitol
water
A
D-Arabinose
B
L-xylose
C
L-gulose
D
D-glucose
Conditions | Yield |
---|---|
at 100℃; |
dihydrogen peroxide
L-gulonic acid ; calcium compound
L-xylose
2,3,4,5-tetra-O-tert-butyldimethylsilyl-L-xylose
L-xylose
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 2h; |
Conditions | Yield |
---|---|
With hydrogenchloride at 90℃; for 0.5h; | A n/a B n/a C 3.5 mg |
5,6-di-O-isopropylidene-D-glucono-1,4-lactone
L-xylose
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 92 percent / pyridine / dimethylformamide / 20 h / 20 °C 2: 100 percent / NaBH4 / tetrahydrofuran; H2O / 2 h / 20 °C 3: 90 percent / pyridine / dimethylformamide / 15 h / 24 °C 4: 92 percent / SnCl2 / CH2Cl2 / 0.5 h / 20 °C 5: 73 percent / Dess-Martin periodinane / CH2Cl2 / 10 h / 20 °C 6: TBAF / tetrahydrofuran / 2 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1: 92 percent / pyridine / dimethylformamide / 20 h / 20 °C 2: 100 percent / NaBH4 / tetrahydrofuran; H2O / 2 h / 20 °C 3: 90 percent / pyridine / dimethylformamide / 15 h / 24 °C 4: 70 percent / BCl3 / CH2Cl2 / 0.08 h / -78 °C 5: 73 percent / Dess-Martin periodinane / CH2Cl2 / 10 h / 20 °C 6: TBAF / tetrahydrofuran / 2 h / 0 °C View Scheme |
2,3-bis-O-(tert-butyldimethylsilyl)-5,6-O-isopropylidene-D-glucono-1,4-lactone
L-xylose
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 100 percent / NaBH4 / tetrahydrofuran; H2O / 2 h / 20 °C 2: 90 percent / pyridine / dimethylformamide / 15 h / 24 °C 3: 92 percent / SnCl2 / CH2Cl2 / 0.5 h / 20 °C 4: 73 percent / Dess-Martin periodinane / CH2Cl2 / 10 h / 20 °C 5: TBAF / tetrahydrofuran / 2 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1: 100 percent / NaBH4 / tetrahydrofuran; H2O / 2 h / 20 °C 2: 90 percent / pyridine / dimethylformamide / 15 h / 24 °C 3: 70 percent / BCl3 / CH2Cl2 / 0.08 h / -78 °C 4: 73 percent / Dess-Martin periodinane / CH2Cl2 / 10 h / 20 °C 5: TBAF / tetrahydrofuran / 2 h / 0 °C View Scheme |
(1R,2S,3S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butane-1,4-diol
L-xylose
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 90 percent / pyridine / dimethylformamide / 15 h / 24 °C 2: 92 percent / SnCl2 / CH2Cl2 / 0.5 h / 20 °C 3: 73 percent / Dess-Martin periodinane / CH2Cl2 / 10 h / 20 °C 4: TBAF / tetrahydrofuran / 2 h / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1: 90 percent / pyridine / dimethylformamide / 15 h / 24 °C 2: 70 percent / BCl3 / CH2Cl2 / 0.08 h / -78 °C 3: 73 percent / Dess-Martin periodinane / CH2Cl2 / 10 h / 20 °C 4: TBAF / tetrahydrofuran / 2 h / 0 °C View Scheme |
(3S,4S)-5,5-Diethoxy-1,3,4-trihydroxy-pentan-2-one
L-xylose
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 69 percent / L-iditol dehydrogenase, triosephosphate isomerase, formate dehydrogenase, sodium formate 2: 95 percent / 0.5 M aq. HCl / tetrahydrofuran View Scheme |
5,6-dideoxy-D-threo-hex-5-en-2-ulose
L-xylose
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 61 percent / phosphate buffer (pH 7.0), sodium formate, NADH sodium salt / H2O / 72 h / Ambient temperature; sorbitol dehydrogenase (EC 1.1.1.14) from sheep liver, formate dehydrogenase (EC 1.2.1.2) from yeast 2: 1.) O3, 2.) Na2SO3 / 1.) MeOH, -78 deg C, 2. a) -78 deg C, 1 h, b) r.t., 15 h View Scheme |
Conditions | Yield |
---|---|
With methanol; water Product distribution / selectivity; Electrochemical reaction; |
Conditions | Yield |
---|---|
With dihydrogen peroxide; Fe2(SO4)3 |
Conditions | Yield |
---|---|
With recombinant alditol oxidase from Streptomyces coelicolor A3(2); catalase from bovine liver at 20℃; for 4h; pH=7.5; Kinetics; Reagent/catalyst; Temperature; pH-value; aq. phosphate buffer; Enzymatic reaction; regioselective reaction; | |
With sulfuric acid; quinolinium dichromate(VI) In water at 19.84℃; Kinetics; Mechanism; Temperature; Reagent/catalyst; |
Conditions | Yield |
---|---|
With hydrogenchloride; water In 1,4-dioxane at 100℃; for 2h; | A n/a B n/a C n/a D 2.4 mg |
Conditions | Yield |
---|---|
With hydrogenchloride; water for 4h; Reflux; |
A
D-Mannose
B
L-xylose
C
D-glucose
D
D-Galactose
E
D-Glucuronic acid
F
D-galacturonic acid
Conditions | Yield |
---|---|
With water; trifluoroacetic acid at 110℃; for 3h; |
Conditions | Yield |
---|---|
With hydrogen In water at 150℃; under 37503.8 Torr; for 2h; Catalytic behavior; Solvent; Concentration; Reagent/catalyst; Temperature; Pressure; Sealed tube; | 98% |
With sodium amalgam | |
With hydrogen; nickel In methanol; ethanol; water at 50℃; under 760.051 Torr; Product distribution / selectivity; | |
With Ru/TiO2; hydrogen In water at 120℃; under 15001.5 Torr; Temperature; Time; Autoclave; |
methanol
L-xylose
(2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol
Conditions | Yield |
---|---|
With hydrogenchloride | 95% |
With hydrogenchloride at 5 - 10℃; | |
With hydrogenchloride Reflux; | |
With sulfuric acid at 20℃; for 5h; | |
Stage #1: methanol; L-xylose With hydrogenchloride at 55℃; for 21h; Stage #2: With silver carbonate In methanol at 25℃; for 0.5h; |
L-xylose
acetone
(3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxane
Conditions | Yield |
---|---|
With malonic acid; choline chloride for 0.666667h; Inert atmosphere; Reflux; | 95% |
With sulfuric acid; copper(II) sulfate at 25℃; for 24h; | 86% |
With sulfuric acid; magnesium sulfate at 20 - 30℃; for 12h; | 84.3% |
Conditions | Yield |
---|---|
In ethanol | 93% |
L-xylose
trans-2-phenylvinylboronic acid
1-amino-2-propene
(6E)-5-(allylamino)-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol
Conditions | Yield |
---|---|
In ethanol at 20℃; for 72h; | 92% |
In ethanol at 20℃; for 16h; Petasis reaction; | 73% |
Conditions | Yield |
---|---|
89% |
Conditions | Yield |
---|---|
In methanol | 88% |
Conditions | Yield |
---|---|
Stage #1: L-xylose; acetone With sulfuric acid; magnesium sulfate at 20 - 24℃; for 17.25h; Industry scale; Stage #2: With hydrogenchloride In water at 20℃; for 6h; pH=2; | 86% |
Stage #1: L-xylose; acetone With magnesium sulphate; sulfuric acid at 20 - 24℃; for 17.25h; Stage #2: With hydrogenchloride In water at 20℃; for 6h; pH=2; | 86% |
With hydrogenchloride; sulfuric acid; copper(II) sulfate Yield given. Multistep reaction; | |
Stage #1: L-xylose; acetone With sulfuric acid; copper(II) sulfate at 20℃; for 24h; Stage #2: With hydrogenchloride at 20℃; for 1h; Further stages.; | |
Stage #1: L-xylose; acetone With sulfuric acid; copper(II) sulfate Stage #2: With hydrogenchloride; water |
L-xylose
Isopropyl acetate
(3aS,5R,6S,6aS)-5-hydroxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxolane-6-ol
Conditions | Yield |
---|---|
Stage #1: L-xylose With sulfuric acid; magnesium sulfate In acetone at 20 - 30℃; Stage #2: With hydrogenchloride In water at 20 - 30℃; for 8h; pH=2-3; Stage #3: Isopropyl acetate In water at 0 - 5℃; for 3h; | 84.2% |
Conditions | Yield |
---|---|
With dimethylbromosulphonium bromide at 0 - 5℃; for 0.583333h; neat (no solvent); | 83% |
With hydrogenchloride | |
With hydrogenchloride | |
With hydrogenchloride for 0.25h; Ambient temperature; |
Conditions | Yield |
---|---|
Stage #1: L-xylose With cerium(III) chloride heptahydrate; silica gel; sodium iodide In acetonitrile for 1h; Stage #2: benzyl acetoacetate In acetonitrile at 50℃; for 24h; | 77% |
L-xylose
2-{5-[5-C-(1,4-anhydro-β-D-erythrotetrofuranosyl)-2-methylfuran-3-yl]-1,3,4-oxadiazol-2-ylthio}acetohydrazide
Conditions | Yield |
---|---|
With acetic acid In ethanol; water Reflux; | 74% |
L-xylose
Conditions | Yield |
---|---|
Stage #1: L-xylose; (R)-tert-butyl (3-(3,5-diamino-6-chloropyrazine-2-carboxamido)-2-(2-methylbenzyl)propyl)(4-((2-(hexylamino)ethyl)carbamoyl)benzyl)carbamate With N-ethyl-N,N-diisopropylamine In methanol at 20℃; for 1h; Stage #2: With sodium cyanoborohydride; acetic acid In methanol at 50℃; for 20h; | 69.7% |
Conditions | Yield |
---|---|
With sulfuric acid at 0 - 30℃; Inert atmosphere; | 64.6% |
Conditions | Yield |
---|---|
Stage #1: L-xylose With bromine; potassium carbonate In water at 0 - 20℃; Stage #2: trityl chloride With pyridine; dmap Heating; | 63% |
Conditions | Yield |
---|---|
In ethanol Ambient temperature; | 61% |
Conditions | Yield |
---|---|
With 1% Pd on activated carbon; hydrogen In water at 140℃; under 37503.8 Torr; for 2h; Reagent/catalyst; Sealed tube; | A n/a B 58% |
L-xylose
ethyl 4-benzyloxyacetoacetate
ethyl 2-methyl-5-(L-threo-1,2,3-trihydroxyprop-1-yl)furan-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: L-xylose With cerium(III) chloride heptahydrate; silica gel; sodium iodide In acetonitrile for 1h; Stage #2: ethyl 4-benzyloxyacetoacetate In acetonitrile at 50℃; for 24h; | 50% |
Conditions | Yield |
---|---|
Stage #1: L-xylose With bromine; potassium carbonate In water at 0 - 20℃; for 2h; Stage #2: benzaldehyde With sulfuric acid In tetrahydrofuran at 0 - 20℃; | 49% |
L-xylose
4-hydroxy-3-(3-(methoxyamino)-1-phenylbutyl)-2H-1-benzopyran-2-one
C25H29NO8
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 50℃; | 45% |
Conditions | Yield |
---|---|
With copper diacetate In methanol; water Reflux; | 40% |
With methanol; copper diacetate | |
With copper diacetate In methanol for 0.166667h; Heating; |
Conditions | Yield |
---|---|
In ethanol at 0℃; | 32% |
L-xylose
(3S)-O-(N-methoxyglycyl)betulinic acid
(3S)-O-(N-methoxy-N-β-L-xylosylglycyl)betulinic acid
Conditions | Yield |
---|---|
In methanol; dichloromethane at 40℃; for 48h; | 27% |
Conditions | Yield |
---|---|
With trifluoroacetic acid In water at 50 - 60℃; for 12h; | 20% |
Conditions | Yield |
---|---|
With sulfuric acid at 5 - 30℃; Inert atmosphere; | 16.7% |
methanol
L-xylose
methyl-xylofuranoside
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; β-methyl-l-xyloside; | |
With hydrogenchloride at 100℃; α-methyl-l-xyloside; |
The CAS registry number of L-(-)-Xylose is 609-06-3. The systematic name is L-xylose. Its EINECS registry number is 210-174-1. In addition, the molecular formula is C5H10O5 and the molecular weight is 150.13. It is a kind of white fine crystalline powder and belongs to the classes of Carbohydrate; Basic Sugars (Mono & Oligosaccharides); Biochemistry; Sugars; Xylose; Carbohydrate Sources (Sugars/Extracts); MonosaccharidesBase Ingredients; Sugars for Media; Carbohydrate Synthesis; Specialty Synthesis; Monosaccharides.
Physical properties about this chemical are: (1)ACD/LogP: -2.39; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.39; (4)ACD/LogD (pH 7.4): -2.39; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.19; (8)ACD/KOC (pH 7.4): 1.19; (9)#H bond acceptors: 5; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 53.99 Å2; (13)Index of Refraction: 1.543; (14)Molar Refractivity: 31.41 cm3; (15)Molar Volume: 99.5 cm3; (16)Polarizability: 12.45 ×10-24cm3; (17)Surface Tension: 81.4 dyne/cm; (18)Density: 1.508 g/cm3; (19)Flash Point: 219.2 °C; (20)Enthalpy of Vaporization: 77.23 kJ/mol; (21)Boiling Point: 415.5 °C at 760 mmHg; (22)Vapour Pressure: 1.22E-08 mmHg at 25°C.
Preparation of L-(-)-Xylose: it can be prepared by 5,5-diethoxy-pentane-1,2,3,4-tetraol. This reaction will need reagent 0.5 M aq. HCl and solvent tetrahydrofuran. The yield is about 95%.
Uses of L-(-)-Xylose: it can react with propylamine to get N-propyl-b-L-arabinopyranosylamine. This reaction will need solvent methanol. The yield is about 88%.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C[C@H](O)[C@@H](O)[C@H](O)CO
(2)InChI: InChI=1/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4+,5+/m0/s1
(3)InChIKey: PYMYPHUHKUWMLA-VPENINKCBR
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