533-67-5

Basic information

• Product Name: 2-Deoxy-D-ribose
• Synonyms: D-.alpha.-Ribodesose;Deoxyribose;D-Ribose, 2-deoxy-;Ribose, 2-deoxy-, D-;2-DEOXYRIBOSE;2-DESOXY-D-RIBOSE;2'-DEOXY-D-RIBOSE;2-DEOXY-D-RIBOSE
• CAS NO: 533-67-5
• Molecular Formula: C₅H₁₀O₄
• Molecular Weight: 134.13
• EINECS: 208-573-0
• Product Categories: Pharmaceutical Raw Materials;FINE Chemical & INTERMEDIATES;13C & 2H Sugars;Riboses and 2'-Deoxyriboses;Biochemistry;Deoxysugars;Nucleosides, Nucleotides & Related Reagents;Ribose;Sugars;Dextrins、Sugar & Carbohydrates;aldehydes;Carbohydrates & Derivatives;nucleoside
• Mol File: 533-67-5.mol
• Article Data: 52

Chemical Properties

• Melting Point: 89-90 °C(lit.)
• Boiling Point: 167.23°C (rough estimate)
• Flash Point: 197.601 °C
• Appearance: White to slightly yellow/Crystalline Powder
• Density: 1.0590 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: -56 ° (C=1, H2O)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
• PKA: 12.61(at 25℃)
• Water Solubility: soluble
• Sensitive: Hygroscopic
• Stability: Hygroscopic
• Merck: 14,2908
• BRN: 1721978
• CAS DataBase Reference: 2-Deoxy-D-ribose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Deoxy-D-ribose(533-67-5)
• EPA Substance Registry System: 2-Deoxy-D-ribose(533-67-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-37/39-36-26
• WGK Germany: 3
• RTECS: SB7230000
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 533-67-5(Hazardous Substances Data)

Usage

Description

2-deoxy-D-Ribose is a reducing sugar formed as a degradation product during metabolism of thymidine by thymidine phosphorylase. It increases levels of reactive oxygen species (ROS) in HL-60 human leukemia cells when used at a concentration of 15 mM. 2-deoxy-D-Ribose (10 μM) induces tubulogenesis and migration of bovine aortic endothelial (BAE) cells. Topical administration of 2-deoxy-D-ribose increases blood vessel formation and accelerates wound healing in a rat full-thickness cutaneous wound model.

Chemical Properties

White powder

Uses

2-Deoxy-D-ribose is used as a precursor to deoxyribonucleic acid. It induces apoptosis by inhibiting the synthesis and increasing the efflux of glutathione. Further, it is used in the synthesis of optically active dipyrrolyl alkanols from pyrroles on the surface of montmorillonite KSF clay.

Definition

ChEBI: 2-deoxy-D-ribose is a deoxypentose that is D-ribose in which the hydroxy group at position C-2 is replaced by hydrogen. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite. It is functionally related to a D-ribose.

Purification Methods

Dissolve 2-deoxy--D-ribose in a little H2O, evaporate to a syrup (in a vacuum), and seed to crystallise. Triturate the crystals with a little EtOAc containing 5% MeOH, decant and dry in vacuum over P2O5. It is best purified via the anilide which separates from a mixture of the ribose (100-125g) in MeOH (100mL) and redistilled aniline (40mL) in a few minutes. After standing for 20hours at room temperature, it is cooled to 0o, filtered, washed with 50% aqueous MeOH and Et2O followed by recrystallisation from ethylene glycol monomethyl ether. The anilide has m 172-173o, [ ] D 25 +46o (equilibrium in pyridine). The anilide (5g), benzaldehyde (5mL) and benzoic acid (0.5g) in H2O (150mL) are shaken mechanically for 2024hours. The aqueous phase is extracted with Et2O (3x), decolourised with a little charcoal and evaporated in a vacuum to a syrup. This is dried over P2O5 in high vacuum. The syrupy sugar weighs 3.1g and crystallises in a few days, but more rapidly on seeding. Triturate it with a little EtOAc containing 5% MeOH, decant and dry it over P2O5. At this stage it has m 78-82o, [ ] D 25 -57o (c 1, H2O final). This is a mixture of and anomers. Pure -anomer is obtained by recrystallisation from EtOAc The -anomer when recrystallised from EtOAc and isoPrOH has m 96-98o, [ ] D 25 -55o (c 0.5, H2O final). [Sowden Biochemical Preparations 5 75 1957.] The mutarotation is as follows: [] D 20.5 +96.3o(0minutes), -76o(33minutes), -56o (24hours) (c 5.8 MeOH). It is moderately hygroscopic and should be kept in a well stoppered bottle. It also crystallises from diethyl ether. [Deriaz et al. J Chem Soc 1879 1949, Beilstein 1 IV 4181, Hauske & Rapoport J Org Chem 4 4 2472 1979.]

InChI:InChI=1/C5H10O4/c6-2-4-3(7)1-5(8)9-4/h3-8H,1-2H2/t3-,4+,5-/m0/s1

Synthetic route

sodium 3-deoxy-D-mannonate (93857-40-0) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
Stage #1: sodium 3-deoxy-D-mannonate With hydrogenchloride In water pH=5; Stage #2: With sodium hypochlorite; acetic acid In water at 40 - 45℃; for 2h; pH=5 - 6;	95%
Stage #1: sodium 3-deoxy-D-mannonate With hydrogenchloride In water pH=5; Stage #2: With hydrogenchloride; sodium hypochlorite; acetaldehyde In water at 40 - 45℃; for 2h; pH=5 - 6;	94%
Stage #1: sodium 3-deoxy-D-mannonate With hydrogenchloride In water pH=5; Stage #2: With hydrogenchloride; sodium hypochlorite; formaldehyd In water at 40 - 45℃; for 2h; pH=5 - 6;	94%

D-arabino-3-deoxy-hexonic acid (1518-59-8) + 3-deoxy-D-arabino-hexono-1,4-lactone (50480-80-3) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
Stage #1: D-arabino-3-deoxy-hexonic acid; 3-deoxy-D-arabino-hexono-1,4-lactone With sodium carbonate In water at 20℃; pH=8.8; Stage #2: With sodium hypochlorite In water for 1 - 4h; pH=4.5 - 5.0; Stage #3: With sodium sulfite In water	93%

(S)-2-Amino-6-{3-[(E)-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-2-methyl-acryloyl]-ureido}-hexanoic acid (87616-31-7) → 2-Deoxy-D-ribose (533-67-5) + (2S)-amino-6-(1-thyminyl)hexanoic acid (76945-38-5)

Conditions	Yield
With pH 10.5 In water at 90℃;	A n/a B 90%

4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With cerium(IV) sulphate; sulfuric acid; palladium 10% on activated carbon In water at 37℃;	51%

potassium 2-dehydro-3-deoxy-D-gluconate → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
Stage #1: potassium 2-dehydro-3-deoxy-D-gluconate With sulfuric acid; hydrogen; palladium 10% on activated carbon In water at 50℃; Stage #2: With calcium carbonate In water Stage #3: With calcium hydroxide; carbon dioxide; dihydrogen peroxide; copper diacetate; iron(II) sulfate more than 3 stages;	47%

6,6-bis-ethanesulfonyl-L-erythro-hex-5-ene-1,2,3-triol → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With ammonium hydroxide

3-deoxy-D-glucose (2490-91-7) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With sodium periodate; water und anschliessend mit wss.Ammoniak;

D-glucose (50-99-7) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With calcium hydroxide; water at 120℃; und Behandeln der vom Calciumhydroxid befreiten, mit Eisen(III)-sulfat und Bariumacetat versetzen Loesung des Reaktionsprodukts mit wss.Wasserstoffperoxid;

3-O-methyl-D-glucose (146-72-5, 2922-60-3, 4682-46-6, 5153-62-8, 32166-87-3, 38088-21-0, 62396-68-3, 65725-72-6, 90364-89-9, 126874-17-7) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With calcium hydroxide; water Erwaermen des Reaktionsprodukts mit Eisen(III)-sulfat,Bariumacetat und wss.Wasserstoffperoxid;

O3-(toluene-4-sulfonyl)-D-glucose (50705-39-0) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With calcium hydroxide; water

D-erythro-[2]pentulose-(2-nitro-phenylhydrazone) (91338-48-6, 91338-49-7) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With water; nickel Hydrogenation.Behandlung des Reaktionsprodukts mit wss.Essigsaeure und Natriumnitrit;

2-deoxy-α-D-erythro-pentofuranose (36792-87-7) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With diclazuril In water-d2 at 43.3℃; Equilibrium constant; Rate constant;

[R-(R*,R*)]-5-Hexene-1,2,3-triol (89534-51-0) → D-threo-2-deoxy-pentose (5284-18-4) + 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With ozone In methanol at -78℃; for 0.75h; Title compound not separated from byproducts;

2-deoxy-D-ribose (36792-88-8) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With diclazuril In water-d2 at 43.3℃; Equilibrium constant; Rate constant;

2'-Deoxyguanosine (961-07-9) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With water; potassium bromide; dinitrogen monoxide Mechanism; Irradiation; G value of product; other reagent - N2/O2 instead of N2O;

4,4-dimethyl-3-<(trimethylsilyl)oxy>pentan-2-one (88264-38-4) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → D-threo-2-deoxy-pentose (5284-18-4) + 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-propionaldehyde (74310-52-4) → D-threo-2-deoxy-pentose (5284-18-4) + 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With acetic acid for 12h; Ambient temperature; Title compound not separated from byproducts;

((4R,5S)-5-[1,3]Dioxolan-2-ylmethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With acid

(S)-5-Guanidino-2-{3-[(E)-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-2-methyl-acryloyl]-ureido}-pentanoic acid (87616-32-8) → 2-Deoxy-D-ribose (533-67-5) + (S)-5-Guanidino-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pentanoic acid (87616-33-9)

Conditions	Yield
In water Heating;

1-(β-D-erythro-3-deoxy-pentofuranosyl)-4-methoxy-1H-pyrimidin-2-one (37117-02-5) → 2-Deoxy-D-ribose (533-67-5) + O2-methyluracil (25902-86-7)

Conditions	Yield
With hydrogenchloride In water at 32℃; Rate constant; pH dependence;

1-(2-deoxy-β-D-erythro-pentofuranosyl)-2-methoxy-5-methyl-4(1H)-pyrimidinone (37085-48-6) → 2-Deoxy-D-ribose (533-67-5) + 2-Methoxy-5-methyl-1H-pyrimidin-4-one (25902-91-4)

Conditions	Yield
With hydrogenchloride In water at 32℃; Rate constant; pH dependence;

2'-deoxy-D-adenosine (958-09-8) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With water; potassium bromide; dinitrogen monoxide Mechanism; Irradiation; G value of product; other reagent - N2/O2 instead of N2O;

(3R)-3,4-dihydro-2H-pyran-3r,4c-diol → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With sulfuric acid

deoxyribonucleic acid substances from the roe of fish → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
Hydrolysis.durch enzymatische Hydrolyse und anschliessende Hydrolyse mit Hilfe eines sauren und eines schwach basischen Ionenaustauschers;

D-erythro-3,4,5-triacetoxy-1-nitro-pent-1-ene → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With ethanol; palladium Hydrogenation.und Behandlung des Reaktionsprodukts mit wss.-aethanol.Natronlauge und anschliessend mit wss.Schwefelsaeure;

methyl- → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With methanol; sodium methylate Erhitzen des Reaktionsprodukts mit wss.Essigsaeure;

methanol (67-56-1) + 2-Deoxy-D-ribose (533-67-5) → 1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5, 51255-18-6, 60134-26-1, 89577-26-4, 96038-80-1, 96039-31-5, 144301-84-8, 144301-85-9)

Conditions	Yield
With hydrogenchloride	100%
With hydrogenchloride	100%
With hydrogenchloride at 0 - 20℃;	98%

methanol (67-56-1) + 2-Deoxy-D-ribose (533-67-5) → 1-O-methyl-α-2-deoxy-D-erythro-pentofuranose (51255-17-5)

Conditions	Yield
With hydrogenchloride at 25℃; for 0.666667h;	99.6%

2-Deoxy-D-ribose (533-67-5) + (2,5-dichlorophenyl)hydrazine (305-15-7) → 2-deoxyribose (2,5-dichlorophenyl)hydrazone

Conditions	Yield
In methanol Heating;	99%

2-Deoxy-D-ribose (533-67-5) + 1-Aminopiperidine (2213-43-6) → (2R,3S)-5-(piperidin-1-ylimino)pentane-1,2,3-triol

Conditions	Yield
In methanol for 1h; Reflux;	98%

2-Deoxy-D-ribose (533-67-5) + 1,1-Diphenylhydrazine (530-50-7) → (R,S,E)-5-[(N,N-diphenyl)hydrazono]pentane-1,2,3-triol

Conditions	Yield
With acetic acid In methanol at 20℃; for 1h;	98%

2-Deoxy-D-ribose (533-67-5) + acetic anhydride (108-24-7) → (3,4,5-triacetoxy)pentanenitrile (49560-18-1)

Conditions	Yield
With ammonium hydroxide; N-Bromosuccinimide at 0℃; for 0.25h;	97%

1.3-propanedithiol (109-80-8) + 2-Deoxy-D-ribose (533-67-5) → 2-deoxy-D-erythro-pentose cyclic 1,3-propanediyl mercaptal (50907-65-8)

Conditions	Yield
With hydrogenchloride; water In chloroform at 20℃;	90%
With hydrogenchloride In chloroform; water at 0 - 20℃; Inert atmosphere;	75%

2-Deoxy-D-ribose (533-67-5) → 2-deoxy-D-ribonolactone (34371-14-7)

Conditions	Yield
With bromine In water at 25℃; for 120h;	88%
With bromine In water at 20℃; for 120h;	78%
With bromine; potassium carbonate In water at 20℃; for 8h;	70%
With bromine In water at 20℃; for 120h; Sealed tube;
With bromine In water at 20℃; for 120h; Sealed tube;

2-Deoxy-D-ribose (533-67-5) + N-aminopyrrolidine (16596-41-1) → (2R,3S)-5-(pyrrolidin-1-ylimino)pentane-1,2,3-triol

Conditions	Yield
In methanol for 1.5h; Reflux;	88%

methanol (67-56-1) + 2-Deoxy-D-ribose (533-67-5) → methyl-2-deoxyribopyranoside (863396-35-4)

Conditions	Yield
With hydrogenchloride	85%

2-Deoxy-D-ribose (533-67-5) + Methyltriphenylphosphonium bromide (1779-49-3) → (2R,3S)-hex-5-ene-1,2,3-triol (79364-36-6)

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 2-Deoxy-D-ribose In tetrahydrofuran at 0 - 40℃; for 24h; Wittig Olefination;	85%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 2-Deoxy-D-ribose In tetrahydrofuran at 35℃; for 24h; Wittig reaction;	75%

2-Deoxy-D-ribose (533-67-5) + ethanethiol (75-08-1) → 2-deoxy-D-erythro-pentose diethyl dithioacetal (115214-11-4)

Conditions	Yield
With hydrogenchloride at 0℃; for 1h; Inert atmosphere;	83%
With hydrogenchloride at 20℃; for 3h;	71%
With hydrogenchloride
With hydrogenchloride

2-Deoxy-D-ribose (533-67-5) + methyl (triphenylphosphoranylidene)acetate (21204-67-1) → methyl (E,5S,6R)-5,6,7-trihydroxyhept-2-enoate (78606-78-7)

Conditions	Yield
benzoic acid In 1,2-dimethoxyethane for 5h; Heating;	82%

2-Deoxy-D-ribose (533-67-5) → lithium 2-deoxy-D-erythro-pentonate (78096-97-6)

Conditions	Yield
With potassium hydroxide; lithium hydroxide; dihydrogen peroxide; magnesium oxide 1.) 2 h, RT, 2.) 18 h, 40 deg C;	80%

2-Deoxy-D-ribose (533-67-5) + dibenzylamine (103-49-1) → (2R,3S)-5-(dibenzylamino)pentane-1,2,3-triol (910658-48-9)

Conditions	Yield
Stage #1: 2-Deoxy-D-ribose; dibenzylamine In dichloromethane for 24h; Stage #2: With sodium tetrahydroborate In dichloromethane at 0 - 20℃; for 3h;	78%

2-Deoxy-D-ribose (533-67-5) + benzyl alcohol (100-51-6) → (3R,4S)-6-Benzyloxy-tetrahydro-pyran-3,4-diol (418760-06-2)

Conditions	Yield
With dimethylsilicon dichloride at 25℃;	76%

2-Deoxy-D-ribose (533-67-5) + tetraallyl tin (7393-43-3) → (2R,3S)-Oct-7-ene-1,2,3,5-tetraol (195196-44-2)

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In ethanol; water; toluene at 70℃; for 5h;	75%

2-Deoxy-D-ribose (533-67-5) + 1-azepanylamine (5906-35-4) → (2R,3S)-5-(azepan-1-ylimino)pentane-1,2,3-triol

Conditions	Yield
In methanol for 0.75h; Reflux;	73%

2-Deoxy-D-ribose (533-67-5) → (2R,3S)-5-aminopentane-1,2,3-triol (64869-48-3)

Conditions	Yield
With ammonium hydroxide; ammonium acetate; sodium cyanoborohydride In ethanol Reflux;	73%
With transaminase biocatalyst ATA256; isopropylamine for 48h; Reagent/catalyst; Enzymatic reaction;	69%

2-Deoxy-D-ribose (533-67-5) + 2,2-dimethoxy-propane (77-76-9) → 3,4-O-isopropylidene-2-deoxy-d-ribose (65236-75-1)

Conditions	Yield
With toluene-4-sulfonic acid In acetone at 0℃;	72%

2-Deoxy-D-ribose (533-67-5) + ethane-1,2-dithiol (540-63-6) → 2-Deoxy-D-ribose Ethylene Mercaptal (43179-62-0)

Conditions	Yield
With hydrogenchloride 1.) 5 deg C, 10 min 2.) 1 h, room temp.;	71%
With hydrogenchloride

Upstream product

• 5336-74-3 2-methylnonane-4,6-dione 
• 5336-72-1 N,N-dimethyl(diphenyl)methanamine 
• 5336-71-0 4-chloro-N-(2,4-difluorophenyl)benzamide 
• 5336-70-9 N,N-dibutyl-3-hydroxy-3-phenylbutanamide 
• 5336-69-6 1,4,6,9-tetrachloro-10H-phenothiazine-2-carbonitrile 
• 5336-68-5 2,2-diethyl-1-phenylbutan-1-ol 
• 5336-67-4 decane-3,5-dione 
• 53366-58-8 (2-Methylpropylidene)cyclopentane 
• 53366-57-7 (2-Methyl-1-propenyl)cyclopentane 
• 53366-56-6 1-methyl-3-methylidenecyclopentane 
• 53366-55-5 Pentylidenecyclopentane 
• 53366-54-4 (2-Methylbutylidene)cyclopentane 
• 53366-53-3 1-(2-Methylbutyl)cyclopentene 
• 53366-51-1 (3-Methylbutylidene)cyclopentane 

Downstream Products

• 5336-75-4 4-(DIETHYLAMINO)BUTANENITRILE 
• 5336-76-5 2-Benzoylbutyric acid methyl ester 
• 5336-77-6 2,3-di(morpholin-4-yl)-1,4-diphenylbutane-1,4-dione 
• 5336-78-7 (2E)-3-phenyl-1-(4-{[(1E)-phenylmethylidene]amino}phenyl)prop-2-en-1-one 
• 5336-80-1 N-(4-{(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl}phenyl)acetamide 
• 5336-81-2 N-(4-{3-[4-(diethylamino)phenyl]acryloyl}phenyl)acetamide 
• 53368-22-2 Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylicacid, 1,4,5,6,7,7-hexachloro-, manganese(2+) salt (1:1) 
• 5336-82-3 [(6-butoxypyridin-3-yl)amino]methanesulfinate 
• 53368-35-7 1-Deoxy-D-allopyranose tetraacetate 
• 53368-43-7 N-{(3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(pyridin-4-ylcarbonyl)hydrazino]tetrahydro-2H-pyran-3-yl}acetamide (non-preferred name) 
• 533-68-6 DL-Ethyl 2-bromobutyrate 
• 5336-86-7 N,N-dibutyl-2,4,6-trimethylbenzenecarboximidamide 
• 53368-67-5 Cholesta-7,9(11)-dien-3β-ol 
• 53368-72-2 (13α,14β,17α)-5α-Lanosta-7,9(11)-dien-3β-ol acetate 

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