609-06-3

Basic information

• Product Name: L-XYLOSE
• Synonyms: XYLOSE;XYLOSE, L;L-XYL;L-(-)-XYLOSE;L-XYLOSE;L-(-)-Xylose, 99+%, mixture of anomers;L(-)XYLOSE 99%;L-Xylose (9CI)
• CAS NO: 609-06-3
• Molecular Formula: C₅H₁₀O₅
• Molecular Weight: 150.13
• EINECS: 210-174-1
• Product Categories: CARBOHYDRATE;Basic Sugars (Mono & Oligosaccharides);Biochemistry;Sugars;Xylose;Carbohydrate Sources (Sugars/Extracts);MonosaccharidesBase Ingredients;Sugars for Media;Carbohydrate Synthesis;Specialty Synthesis;Monosaccharides
• Mol File: 609-06-3.mol
• Article Data: 21

Chemical Properties

• Melting Point: 150-152 °C(lit.)
• Boiling Point: 191.65°C (rough estimate)
• Flash Point: 219.2 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.525
• Vapor Pressure: 9.92E-06mmHg at 25°C
• Refractive Index: -20 ° (C=10, H2O)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: H2O: 0.1 g/mL, clear, colorless
• PKA: 12.46±0.20(Predicted)
• Water Solubility: within almost transparency
• Sensitive: Hygroscopic
• BRN: 1723080
• CAS DataBase Reference: L-XYLOSE(CAS DataBase Reference)
• NIST Chemistry Reference: L-XYLOSE(609-06-3)
• EPA Substance Registry System: L-XYLOSE(609-06-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 609-06-3(Hazardous Substances Data)

Usage

Chemical Properties

L-Xylose is a white fine crystalline powder. It is an aldopentose that has a molecular formula C5H10O5 and a molar mass of 150.13 g/mol. The structure of L-xylose is presented in Figure 1. The optical rotations of D- and L-xylose are α20D = -18.6° and α20D = +18.6°, respectively (Fischer and Ruff, 1900). L-Xylose can exist in open chain form, as a pyranose or as a furanose. The relative concentrations of different stereoisomers have not been specified for L-xylose. However, for D-xylose the distribution of different forms in water are: 36.5% α-pyranose, 6% β-pyranose and less than 1 % in open chain and furanose form (Pastinen, 2000). Most likely L-xylose acts similarly to its enantiomer, and thus pyranose rings are predominant.Figure 1. Structure of L-xylose A) as a Fischer projection, B) as a ball and stick model in acyclic form and C) as a ball and stick model in pyranose ring form.

Uses

L-Xylose is used in the synthesis of L-Xylose derivatives as selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.

Application

l-Xylose is a suitable starting material for the production of L-ribonucleosides. L- Xylose can be converted into an L-ribose derivative via oxidation and reduction steps. This product is then glycosylated to give L-ribonucleosides: L-uridine, L-cytidine, L- adenosine and L-guanosine (Moyroud and Strazewski, 1999; Chelain et al., 1995).L-Xylose can also be used as a starting material for the production of polyhydroxypyrrolidines and related analogues. These compounds have many biological activities. They are shown to have anti-HIV effects, inhibit tumor growth, and also act as ?- and ?-glucosidase inhibitors, which is of relevance for the development of diabetes drugs (Behr and Guillerm, 2007).

Preparation

L-Xylose can be produced from L-xylulose by isomerization. This can be achieved either enzymatically or chemically under alkaline conditions. The equilibrium of the reaction between D-xylose and D-xylulose in an aqueous solution has been determined at pH 6.8-7.4 and at 25 °C to be 85:15 in favor of D-xylose (Tewari et al., 1985).

Definition

ChEBI: Aldehydo-L-xylose is a xylose of ring-opened form having L-configuration.

InChI:InChI=1/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5-/m0/s1

Synthetic route

(2S,3R,4S)-5,5-Diethoxy-pentane-1,2,3,4-tetraol (124244-64-0) → L-xylose (609-06-3)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran	95%

Tetra-O-acetyl-aldehydo-L-xylose (1195193-89-5) → L-xylose (609-06-3)

Conditions	Yield
With sodium ethanolate at 20 - 30℃;	92%

L-arabinose (5328-37-0) → L-xylose (609-06-3) + L-lyxose (1949-78-6) + L-ribose (24259-59-4)

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 (139404-79-8) → L-xylose (609-06-3)

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 (137491-74-8) → L-xylose (609-06-3)

Conditions	Yield
Yield given. Multistep reaction;

water (7732-18-5) + ascorbic acid (50-81-7) → furfural (98-01-1) + L-xylose (609-06-3) + carbon dioxide (124-38-9)

O1,O3;O2,O4-diethylidene-D-glucitol → L-xylose (609-06-3)

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;

O2,O4-benzylidene-D-glucitol → L-xylose (609-06-3)

Conditions	Yield
With lead(IV) acetate; acetic acid Erwaermen des Reaktionsprodukts mit wss.Essigsaeure;
With water; periodic acid Erwaermen des Reaktionsprodukts mit Essigsaeure;

O2,O4-furfurylidene-D-glucitol → L-xylose (609-06-3)

Conditions	Yield
With lead(IV) acetate; ammonium hydroxide; acetic acid anschliessendes Erhitzen;

(S)-cyclohexylidene glyceraldehyde (78008-36-3, 92822-62-3, 99744-77-1) + polymer bonded 2-phenyl-1,3,2-dioxaborole → L-xylose (609-06-3) + L-lyxose (1949-78-6) + L-ribose (24259-59-4) + L-arabinose (5328-37-0)

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 (78008-36-3, 92822-62-3, 99744-77-1) + polymer bound 1,3,2-dioxaborole → L-xylose (609-06-3) + L-lyxose (1949-78-6) + L-ribose (24259-59-4) + L-arabinose (5328-37-0)

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given;

D-sorbitol (50-70-4) + water (7732-18-5) + manganese (IV)-oxide → D-Arabinose (10323-20-3) + L-xylose (609-06-3) + L-gulose (6027-89-0) + D-glucose (50-99-7)

Conditions	Yield
at 100℃;

dihydrogen peroxide (7722-84-1) + L-gulonic acid ; calcium compound (5743-42-0, 66905-23-5, 126259-97-0) + ferriacetate → L-xylose (609-06-3)

2,3,4,5-tetra-O-tert-butyldimethylsilyl-L-xylose (405218-68-0) → L-xylose (609-06-3)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 2h;

1'-O-((E)-3-O-β-D-glucopyranosyl-caffeoyl) α-L-xylopyranosyl-(4''-2')-β-D-glucopyranoside → L-xylose (609-06-3) + D-glucose (50-99-7) + caffeic acid (331-39-5)

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 (100227-29-0) → L-xylose (609-06-3)

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 (196494-81-2) → L-xylose (609-06-3)

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 (280561-89-9) → L-xylose (609-06-3)

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 (124244-63-9) → L-xylose (609-06-3)

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 (143106-69-8) → L-xylose (609-06-3)

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

sodium gluconate (6027-87-8) → L-xylose (609-06-3)

Conditions	Yield
With methanol; water Product distribution / selectivity; Electrochemical reaction;

L-gulono-1,4-lactone (1128-23-0) → L-xylose (609-06-3)

Conditions	Yield
With dihydrogen peroxide; Fe2(SO4)3

XYLITOL (87-99-0) → L-xylose (609-06-3)

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;

2α,3β-dihydroxy-5α-pregn-16-en-20-one-3-O-{β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside} → L-xylose (609-06-3) + D-glucose (50-99-7) + D-Galactose (59-23-4) + 2α,3β-dihydroxy-5α-pregna-16-en-20-one

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

3-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl]-2β,3β,16α-trihydroxyolean-12-en-23,28-dioic acid-28-O-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside → L-xylose (609-06-3) + L-arabinose (5328-37-0) + D-quionovose (7658-08-4) + D-glucose (50-99-7)

Conditions	Yield
With hydrogenchloride; water for 4h; Reflux;

acid polysaccharide from Boletus edulis → D-Mannose (3458-28-4) + L-xylose (609-06-3) + D-glucose (50-99-7) + D-Galactose (59-23-4) + D-Glucuronic acid (6556-12-3) + D-galacturonic acid (685-73-4)

Conditions	Yield
With water; trifluoroacetic acid at 110℃; for 3h;

L-xylose (609-06-3) → XYLITOL (87-99-0)

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 (67-56-1) + L-xylose (609-06-3) → (2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol (13039-67-3)

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 (609-06-3) + acetone (67-64-1) → (3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxane (131156-47-3)

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%

L-xylose (609-06-3) + ethylamine (75-04-7) → N-ethyl-β-L-arabinopyranosylamine (93253-22-6)

Conditions	Yield
In ethanol	93%

L-xylose (609-06-3) + trans-2-phenylvinylboronic acid (6783-05-7) + 1-amino-2-propene (107-11-9) → (6E)-5-(allylamino)-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol (691905-77-8)

Conditions	Yield
In ethanol at 20℃; for 72h;	92%
In ethanol at 20℃; for 16h; Petasis reaction;	73%

L-xylose (609-06-3) + phenylhydrazine (100-63-0) → D-xylose phenylhydrazone

Conditions	Yield
	89%

propylamine (107-10-8) + L-xylose (609-06-3) → N-propyl-β-L-arabinopyranosylamine (93303-81-2)

Conditions	Yield
In methanol	88%

L-xylose (609-06-3) + acetone (67-64-1) → 1,2-O-isopropylidene-α-L-xylofuranose (114861-22-2)

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 (609-06-3) + Isopropyl acetate (108-21-4) → (3aS,5R,6S,6aS)-5-hydroxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxolane-6-ol (1352955-16-8)

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%

L-xylose (609-06-3) + ethanethiol (75-08-1) → L-xylose diethyl dithioacetal (23259-79-2)

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;

L-xylose (609-06-3) + benzyl acetoacetate (5396-89-4) → benzyl 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: benzyl acetoacetate In acetonitrile at 50℃; for 24h;	77%

L-xylose (609-06-3) + 2-{5-[5-C-(1,4-anhydro-β-D-erythrotetrofuranosyl)-2-methylfuran-3-yl]-1,3,4-oxadiazol-2-ylthio}acetohydrazide (1338470-77-1) → D-xylose 2-{5-[5-(1,4-anhydro-β-D-erythrotetrofuranosyl)-2-methylfuran-3-yl]-1,3,4-oxadiazol-2-ylthio}acetohydrazone

Conditions	Yield
With acetic acid In ethanol; water Reflux;	74%

L-xylose (609-06-3) + (R)-tert-butyl (3-(3,5-diamino-6-chloropyrazine-2-carboxamido)-2-(2-methylbenzyl)propyl)(4-((2-(hexylamino)ethyl)carbamoyl)benzyl)carbamate → tert-butyl ((R)-3-(3,5-diamino-6-chloropyrazine-2-carboxamido)-2-(2-methylbenzyl)propyl)(4-((2-(hexyl((2R,3S,4S)-2,3,4,5-tetrahydroxypentyl)amino)ethyl)carbamoyl)benzyl)carbamate

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%

L-xylose (609-06-3) + cyclohexanone (108-94-1) → C17H26O5

Conditions	Yield
With sulfuric acid at 0 - 30℃; Inert atmosphere;	64.6%

L-xylose (609-06-3) + trityl chloride (76-83-5) → 5-O-trityl-L-xylono-γ-lactone (868159-65-3)

Conditions	Yield
Stage #1: L-xylose With bromine; potassium carbonate In water at 0 - 20℃; Stage #2: trityl chloride With pyridine; dmap Heating;	63%

L-xylose (609-06-3) + ethylamine (75-04-7) + hydrogen cyanide → 2-deoxy-2-(ethylamino)-L-glucononitrile (93253-24-8)

Conditions	Yield
In ethanol Ambient temperature;	61%

L-xylose (609-06-3) → Tetrahydrofurfuryl alcohol (97-99-4) + XYLITOL (87-99-0)

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 (609-06-3) + ethyl 4-benzyloxyacetoacetate (67354-34-1) → ethyl 2-methyl-5-(L-threo-1,2,3-trihydroxyprop-1-yl)furan-3-carboxylate (1581292-10-5)

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%

L-xylose (609-06-3) + benzaldehyde (100-52-7) → (2R,4aS,7S,7aS)-7-hydroxy-2-phenyltetrahydro-6H-furo[3,2-d][1,3]dioxin-6-one

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 (609-06-3) + 4-hydroxy-3-(3-(methoxyamino)-1-phenylbutyl)-2H-1-benzopyran-2-one (1101852-85-0) → C25H29NO8 (1207170-43-1)

Conditions	Yield
With acetic acid In N,N-dimethyl-formamide at 50℃;	45%

L-xylose (609-06-3) → L-xylosone (3445-23-6)

Conditions	Yield
With copper diacetate In methanol; water Reflux;	40%
With methanol; copper diacetate
With copper diacetate In methanol for 0.166667h; Heating;

propylamine (107-10-8) + L-xylose (609-06-3) + hydrogen cyanide → 2-deoxy-2-(propylamino)-L-glucononitrile (93253-26-0)

Conditions	Yield
In ethanol at 0℃;	32%

L-xylose (609-06-3) + (3S)-O-(N-methoxyglycyl)betulinic acid (1101863-07-3) → (3S)-O-(N-methoxy-N-β-L-xylosylglycyl)betulinic acid (1101863-47-1)

Conditions	Yield
In methanol; dichloromethane at 40℃; for 48h;	27%

L-xylose (609-06-3) + thiophenol (108-98-5) → (2S,3R,4S)-5,5-bis(phenylthio)pentane-1,2,3,4-tetraol

Conditions	Yield
With trifluoroacetic acid In water at 50 - 60℃; for 12h;	20%

L-xylose (609-06-3) + cyclopentanone (120-92-3) → C15H22O5 (189949-14-2)

Conditions	Yield
With sulfuric acid at 5 - 30℃; Inert atmosphere;	16.7%

methanol (67-56-1) + L-xylose (609-06-3) → methyl-xylofuranoside (1824-96-0, 1824-97-1, 3795-68-4, 3795-69-5, 4229-54-3, 5531-18-0, 7473-45-2, 13039-63-9, 13039-64-0, 13039-65-1, 13039-67-3, 22416-73-5, 22861-09-2, 25129-51-5, 52485-92-4, 52689-55-1, 52689-56-2, 56607-40-0, 72880-70-7, 79083-42-4, 86782-30-1, 86782-31-2, 89615-03-2, 89673-67-6, 89707-99-3, 102045-32-9, 135910-17-7)

Conditions	Yield
With hydrogenchloride at 100℃; β-methyl-l-xyloside;
With hydrogenchloride at 100℃; α-methyl-l-xyloside;

hydrogen cyanide (74-90-8) + L-xylose (609-06-3) → D-gulono-1,4-lactone (6322-07-2)

Upstream product

• 139404-79-8 (2S,3S,4R)-5-hexene-1,2,3,4-tetrol 
• 137491-74-8 3,4,5,6-tetra-O-acetyl-1,2-dideoxy-L-xylo-hex-1-enitol 
• 7732-18-5 water 
• 50-81-7 ascorbic acid 
• 50-70-4 D-sorbitol 
• 7722-84-1 dihydrogen peroxide 
• 5743-42-0 L-gulonic acid ; calcium compound 
• 87-99-0 XYLITOL 
• 453-17-8 D-Glyceraldehyde 
• 141-46-8 Glycolaldehyde 
• 56-82-6 Glyceraldehyde 
• 96-26-4 dihydroxyacetone 
• 19192-62-2 Ribo-pentodialdose 
• 608-66-2 D-galactitol 

Downstream Products

• 903637-88-7 4,5-Bis-(phenyl-hydrazono)-pentane-1,2,3-triol 
• 849585-22-4 LACTIC ACID 
• 822-36-6 4-methyl-1H-imidazole 
• 87-99-0 XYLITOL 
• 1518-62-3 2,4-dihydroxybutanoic acid 
• 21569-62-0 D-erythro-3-deoxy-pentonic acid 
• 21569-63-1 3-Desoxy-D-threo-pentonsaeure 
• 488-30-2 D-xylonic acid 
• 26048-51-1 1-nitro-L-xylo-3.4.5.6-tetraacetoxy-hexene-(1) 
• 131156-47-3 (3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxane 
• 78088-17-2 per-O-acetyl-β-L-xylopyranose 
• 95002-56-5 O²,O⁴;O³,O⁵-((S,R)-dibenzylidene)-L-xylose-dimethylacetal 
• 7473-43-0 1,2,3,4-tetra-O-benzoyl-L-xylopyranose 
• 74675-01-7 L-xylose-(4-nitro-phenylhydrazone) 

Relevant articles and documents

Steroidal glycosides from the underground parts of Hosta ventricosa and their anti-inflammatory activities in mice

Two new pregnane glycosides, 2α, 3β-dihydroxy-5α-pregn-16-en-20-one-3-O-{α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside} (1) and 2α, 3β-dihydroxy-5α-pregn-16-en-20-one-3-O-{β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside}(2), have been isolated along with two known spirostanol saponins from the underground parts of Hosta ventricosa. Their structures were elucidated on the basis of chemical and spectral evidence. The anti-inflammatory activities of these steroidal glycosides were evaluated using a xylene-induced ear edema model. Our results indicated that the compounds exhibited promising anti-inflammatory activities.

Electrochemical Activation of Galactose Oxidase: Mechanistic Studies and Synthetic Applications

The enzyme galactose oxidase (GOase) is a copper radical oxidase that catalyzes the aerobic oxidation of primary alcohols to the aldehydes and has been utilized to that end in large-scale pharmaceutical processes. To maintain its catalytic activity and ensure high substrate conversion, GOase needs to be continuously (re)activated by 1e- oxidation of the constantly formed out-of-cycle species (GOasesemi) to the catalytically active state (GOaseox). In this work, we report an electrochemical activation method for GOase that replaces the previously used expensive horseradish peroxidase activator in a GOase-catalyzed oxidation reaction. First, the formation of GOaseox of a specifically engineered variant via nonenzymatic oxidation of GOasesemi was studied by UV-vis spectroscopy. Second, electrochemical oxidation of GOase by mediators was studied using cyclic voltammetry. The electron-transfer rates between GOase and various mediators at different pH values were determined, showing a dependence on both the redox potential of the mediator and the pH. This observation suggests that the oxidation of GOase by mediators at pH 7-9 likely occurs via a concerted proton-coupled electron-transfer (PCET) mechanism under anaerobic conditions. Finally, this electrochemical GOase activation method was successfully applied to the development of a bioelectrocatalytic GOase-mediated aerobic oxidation of benzyl alcohol derivatives, cinnamyl alcohol, and aliphatic polyols, including the desymmetrizing oxidation of 2-ethynylglycerol, a key step in the biocatalytic cascade used to prepare the promising HIV therapeutic islatravir.

Kinetics and mechanism of quinolinium dichromate mediated oxidation of sugar alcohols in Bronsted acid media

Bronsted acid catalyzed oxidation of certain sugar alcohols (polyols) has been studied by quinolinium dichromate (QDC) using aqueous sulfuric, perchloric, and hydrochloric acids at different temperatures. At constant acidity, reaction kinetics revealed the second-order kinetics with a first order in [Alcohol] and [QDC]. Zucker-Hammett, Bunnett, and Bunnett-Olsen criteria were used to analyze acid-dependent rate accelerations. Bunnett-Olsen plots of (log k + Hν) versus (Hν + log [H+]), and (log k) versus (Hν + log [H+]) afforded slope values (? and ?*, respectively)?>?0.47, suggesting that a water molecule acts as a prton transfer agent in the slow step of the mechanism in the oxidation of alcohols by QDC in the presence of aqueous sulfuric, perchloric, and hydrochloric acids.