1949-78-6

Basic information

• Product Name: L-LYXOSE
• Synonyms: L-LYXOSE, 99%, MIXTURE OF ANOMERS;L-Lyxose (9CI);L(+)-Lyxose, mixture of anomers;L-LYXOSE2;L(+) LYXOSE extrapure;L-lyxo-Pentose;L-Lyxose ,98%;L-LYXOPYRANOSE
• CAS NO: 1949-78-6
• Molecular Formula: C₅H₁₀O₅
• Molecular Weight: 150.13
• EINECS: 217-763-2
• Product Categories: CARBOHYDRATE;13C & 2H Sugars;Basic Sugars (Mono & Oligosaccharides);Biochemistry;Lyxose;Sugars;aldehydes;Carbohydrates & Derivatives
• Mol File: 1949-78-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 108-112 °C(lit.)
• Boiling Point: 191.65°C (rough estimate)
• Flash Point: 155.3 °C
• Appearance: white fine crystalline powder
• Density: 1.1897 (rough estimate)
• Vapor Pressure: 1.22E-08mmHg at 25°C
• Refractive Index: 14 ° (C=1, H2O)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Methanol (Slightly, Heated), Water (Slightly)
• PKA: 12.46±0.20(Predicted)
• Water Solubility: Very soluble (586 g/L) (25°C) in water.
• Sensitive: Hygroscopic
• CAS DataBase Reference: L-LYXOSE(CAS DataBase Reference)
• NIST Chemistry Reference: L-LYXOSE(1949-78-6)
• EPA Substance Registry System: L-LYXOSE(1949-78-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-26
• WGK Germany: 3
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 1949-78-6(Hazardous Substances Data)

Usage

Chemical Properties

white fine crystalline powder

Uses

It acts as a reducing carbohydrate present in maple syrup. It is used in molecular modeling calculations in the study of drug binding and recognition in relation to aldose reductase. L-Lyxose is also utilized by Escherichia coli, encoding a kinase for L-Xylulose.

Definition

ChEBI: An L-lyxose in cyclic pyranose form.

Purification Methods

The 
anomer crystallises from propan-1-ol or EtOH, and the 
anomer crystallises from propan-2-ol. The 2,4-dinitrophenylhydrazone has m 171-172o and [] D -31o (pyridine). In D2O it has 21% of the 
pyranose form. The 2-methyl ether has m 120-121o and [] D +6o (c 1, H2O). [Angyal Adv Carbohydr Chem 42 15 1984, Bently J Am Chem Soc 79 1720 1959, Beilstein 1 I 439, 1 IV 4232.]

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

Synthetic route

2,3-O-isopropylidene-L-lyxofuranose (4099-88-1, 67814-68-0, 70266-87-4, 76249-50-8, 76249-51-9, 93451-15-1) → L-lyxose (1949-78-6)

Conditions	Yield
With water at 20℃;	95%

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%

calcium salt of/the/ L-galactonic acid → L-lyxose (1949-78-6)

Conditions	Yield
With dihydrogen peroxide; iron(III) acetate

L-galactonic acid (133-42-6, 488-33-5, 526-95-4, 526-97-6, 576-36-3, 642-99-9, 1114-17-6, 3956-93-2, 6906-37-2, 7760-07-8, 13382-27-9, 20246-33-7, 20246-35-9, 20246-52-0, 20246-53-1, 21675-42-3, 22430-69-9, 24871-35-0, 28223-42-9, 51547-37-6, 28278-17-3) + dihydrogen peroxide (7722-84-1) + ferriacetate → L-lyxose (1949-78-6)

Conditions	Yield
das Calciumsalz reagiert;

l-galactonate calcium → L-lyxose (1949-78-6)

Conditions	Yield
With ferriacetate; dihydrogen peroxide

(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;

(4R,5S)-4-((R)-1-hydroxy-2,2-dimethoxyethyl)-2,2-dimethyl-1,3-dioxan-5-ol (888487-02-3) → L-lyxose (1949-78-6)

Conditions	Yield
With Dowex 50W2-100 In water at 20℃; for 6.5h;

(4S,1'R)-4-(1'-hydroxy-2',2'-dimethoxyethyl)-2,2-dimethyl-1,3-dioxan-5-one (850252-47-0) → L-lyxose (1949-78-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH(OAc)3; AcOH / CH2Cl2 / 5 h / -20 °C 2: Dowex 50W2-100 / H2O / 6.5 h / 20 °C View Scheme

(4R)-4-((R)-1-(tert-butyldimethylsilyloxy)-2,2-dimethoxyethyl)-2,2-dimethyl-1,3-dioxan-5-ol → L-lyxose (1949-78-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: TBAF / tetrahydrofuran 2: Dowex 50W2-100 / H2O / 6.5 h / 20 °C View Scheme

D-Arabitol (488-82-4) → D-ribulose (488-84-6) + L-xylulose (527-50-4) + D-Arabinose (10323-20-3) + L-lyxose (1949-78-6)

Conditions	Yield
With sulfuric acid; platinum on activated charcoal Electrochemical reaction; Inert atmosphere;

D-Arabitol (488-82-4) → formic acid (64-18-6) + D-Arabinose (10323-20-3) + L-lyxose (1949-78-6)

Conditions	Yield
With sulfuric acid; platinum on activated charcoal Electrochemical reaction; Inert atmosphere;

L-lyxose (1949-78-6) + ethanethiol (75-08-1) → L-Lyxose diethyl dithioacetal (22249-18-9)

Conditions	Yield
With hydrogenchloride In water at 0℃; for 2h; Inert atmosphere;	95%

L-lyxose (1949-78-6) → furfural (98-01-1)

Conditions	Yield
With 1-methyl-3-(4-sulfobutyl)-1H-imidazol-3-ium hydrogensulfate; 4-methyl-2-pentanone In water at 150℃; under 760.051 Torr; for 0.416667h; Autoclave;	91.4%

L-lyxose (1949-78-6) → L-xylulose 1-phosphate

Conditions	Yield
With ATP multistep reaction, enzymatic conversion of aldoses to ketose 1-phosphates (KM and Vmax for most of the steps given);	78%
With ATP 1) L-rhamnose isomerase, tris buffer pH 8.0, mercaptoethanol, MgCl2, ATP (cat.), 2) L-rhamnulose kinase, PEP/pyruvate kinase; Yield given. Multistep reaction;

L-lyxose (1949-78-6) + acetic anhydride (108-24-7) + allyl bromide (106-95-6) → 4,5,6,7,8-penta-O-acetyl-1,2,3-trideoxy-L-galacto-oct-1-enitol + C18H26O10

Conditions	Yield
Stage #1: L-lyxose; allyl bromide With indium In ethanol at 20℃; for 3h; sonication; Stage #2: acetic anhydride With pyridine; dmap at 20℃; for 18h; Further stages.;	A 75% B n/a

methanol (67-56-1) + L-lyxose (1949-78-6) → Methyl α-L-lyxopyranoside (36793-06-3)

Conditions	Yield
Stage #1: methanol With acetyl chloride at 0℃; for 0.5h; Stage #2: L-lyxose at 0 - 20℃; for 12h; Stage #3: With pyridine at 20℃; for 3h;	68%

L-lyxose (1949-78-6) + dichloromethane (75-09-2) + methanol hydrochloride (101752-05-0) + acetyl chloride (75-36-5) → Methyl α-L-lyxopyranoside (36793-06-3)

Conditions	Yield
In methanol; ethyl acetate	67%

2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl iodide (53008-62-1, 53008-61-0) + L-lyxose (1949-78-6) + N-ethyl-N,N-diisopropylamine (7087-68-5) → 2,3-O-isopropylidene-5-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-D-lyxofuranose

Conditions	Yield
Stage #1: L-lyxose With sulfuric acid In acetone at 20℃; for 4h; Inert atmosphere; Stage #2: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl iodide; N-ethyl-N,N-diisopropylamine With tetra-(n-butyl)ammonium iodide In acetone; toluene at 65℃; for 1.16667h; Inert atmosphere; Molecular sieve; regioselective reaction;	63%

L-lyxose (1949-78-6) + D-lyxose (1114-34-7) → rac-lyxose (50-69-1, 58-86-6, 65-42-9, 147-81-9, 609-06-3, 1114-34-7, 1949-78-6, 5328-37-0, 10323-20-3, 20235-19-2, 24259-59-4, 25990-60-7, 34466-20-1, 41247-05-6, 53106-52-8, 55058-43-0, 80952-57-4)

Conditions	Yield
With water

L-lyxose (1949-78-6) + (2-amino-4,5-dimethyl-phenyl)-carbamic acid ethyl ester (873389-62-9) → 1-(6-ethoxycarbonylamino-3.4-dimethyl-anilino)-1-deoxy-L-lyxitol

Conditions	Yield
With methanol anschliessendes Hydrieren an Nickel oder Palladium;

L-lyxose (1949-78-6) → L-lyxonic acid (4172-43-4)

Conditions	Yield
With methanol; potassium hydroxide; iodine

L-lyxose (1949-78-6) + 4-amino-o-xylene (95-64-7) → 5-(3,4-dimethyl-anilino)-5-deoxy-L-arabitol (906331-23-5)

Conditions	Yield
With methanol; Raney. nickel at 100℃; under 73550.8 Torr; Hydrogenation;
With hydrogenchloride; Raney. nickel at 80℃; under 44130.5 Torr; Hydrogenation;

L-lyxose (1949-78-6) + (4-bromophenyl)hydrazine (589-21-9) → lyxose-(4-bromo-phenylhydrazone) (10018-08-3, 18841-81-1, 20603-24-1, 20664-64-6, 72748-84-6, 78039-46-0, 100016-91-9)

Conditions	Yield
With ethanol -<4-bromo-phenylhydrazone>;

L-lyxose (1949-78-6) + L-(-)-α-methylbenzylamine (2627-86-3) + acetic anhydride (108-24-7) → Acetic acid (1S,2S,3S)-2,3,4-triacetoxy-1-{[acetyl-(1-phenyl-ethyl)-amino]-methyl}-butyl ester (79526-48-0, 79549-54-5, 79549-55-6, 79549-57-8, 79549-58-9, 79549-59-0, 79549-60-3, 79549-61-4, 83680-88-0)

Conditions	Yield
With pyridine; sodium cyanoborohydride 1.) methanol-water 2.) 100 deg C, 1 h; Multistep reaction;

L-lyxose (1949-78-6) + (-)-α-methylbenzylamine (2627-86-3) + acetic anhydride (108-24-7) → Acetic acid (1S,2S,3S)-2,3,4-triacetoxy-1-{[acetyl-((S)-1-phenyl-ethyl)-amino]-methyl}-butyl ester (79526-48-0, 79549-54-5, 79549-55-6, 79549-57-8, 79549-58-9, 79549-59-0, 79549-60-3, 79549-61-4, 83680-88-0)

Conditions	Yield
With pyridine; sodium cyanoborohydride 1.)Methanol, water, room temp. 2.)100 deg C, 1 hour; Multistep reaction;

L-lyxose (1949-78-6) → lyxonic acid-1,4-lactone (104196-15-8)

Conditions	Yield
With hypoiodous acid

methanol (67-56-1) + L-lyxose (1949-78-6) + benzoyl chloride (98-88-4) → 1-O-methyl-2,3,5-tri-O-benzoyl-L-lyxofuranose (169529-25-3)

Conditions	Yield
With pyridine; sulfuric acid

L-lyxose (1949-78-6) → L-(-)-arabitol (7643-75-6)

Conditions	Yield
With monospecific xylose reductase from yeast Candida intermedia; NADPH In phosphate buffer at 25℃; pH=7.0; Enzyme kinetics; Further Variations:; Reagents;

L-lyxose (1949-78-6) + allyl alcohol (107-18-6) → allyl α/β-L-lyxofuranoside

Conditions	Yield
With sulfuric acid; sodium sulfate at 25℃;

L-lyxose (1949-78-6) + O-benzylhydoxylamine hydrochloride (2687-43-6) → (2S,3S,4S,E)-2,3,4,5-tetrahydroxypentanal O-benzyl oxime

Conditions	Yield
With pyridine In ethanol for 24h;

Upstream product

• 50-00-0 formaldehyd 
• 608-66-2 D-galactitol 
• 7732-18-5 water 
• 96-26-4 dihydroxyacetone 
• 141-46-8 Glycolaldehyde 
• 56-82-6 Glyceraldehyde 
• 1114-34-7 D-lyxose 
• 2595-05-3 Diacetone D-glucose 
• 63846-98-0 1,2-O-(1-Methylethylidene)-α-D-ribo-pentodialdo-1,4-furanose 
• 4495-04-9 1,2-O-isopropylidene-α-D-allofuranose 
• 453-17-8 D-Glyceraldehyde 
• 19192-62-2 Ribo-pentodialdose 
• 50-69-1 D-ribose 
• 24259-59-4 L-ribose 

Downstream Products

• 50-69-1 rac-lyxose 
• 98-01-1 furfural 
• 36793-06-3 Methyl α-L-lyxopyranoside 
• 22249-18-9 L-Lyxose diethyl dithioacetal 
• 5531-18-0 1-O-methyl α-L-lyxofuranoside 
• 72880-70-7 Methyl-α-D-ribofuranosid 
• 33509-64-7 methyl-β-D-lyxopyranoside 
• 18449-76-8 methyl α-D-lyxopyranoside 
• 164712-83-8 1-O-methyl 2,3,5-tri-O-benzoyl-α-L-lyxofuranoside 
• 4099-88-1 2,3-O-isopropylidene-L-lyxofuranose 
• 87614-44-6 2,4,6-Trimethyl-benzenesulfonic acid (2S,3R,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester 

Relevant articles and documents

L-Ribose: An easily prepared rare sugar

A method to synthesize L-ribose was described by molybdate-catalyzed epimerization of the readily available L-arabinose. The synthesis is one-step and except for a catalytic amount of molybdic acid do not require any expensive reagents, while the solvents used are water and a small amount of methanol. The process can be carried out in 2-3 days. Although the yield of L-ribose is only 20%, being in equilibrium with arabinose, most of the unreacted arabinose is recoverable and can be used again.

A heterogeneous Pd-Bi/C catalyst in the synthesis of l-lyxose and l-ribose from naturally occurring d-sugars

A critical step in the synthesis of the rare sugars, l-lyxose and l-ribose, from the corresponding d-sugars is the oxidation to the lactone. Instead of conventional oxidizing agents like bromine or pyridinium dichromate, it was found that a heterogeneous catalyst, Pd-Bi/C, could be used for the direct oxidation with molecular oxygen. The composition of the catalyst was optimized and the best results were obtained with 5:1 atomic ratio of Pd:Bi. The overall yields of the five-step procedure to l-ribose and l-lyxose were 47% and 50%, respectively. The synthetic procedure is advantageous from the viewpoint of overall yield, reduced number of steps, and mild reaction conditions. Furthermore, the heterogeneous oxidation catalyst can be easily separated from the reaction mixture and reused with no loss of activity.