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958-09-8

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  • 2-dA/2’-Deoxyadenosine/deoxy nucleoside / group protection/white powder with CAS NO. 958-09-8/ worldwide Top Pharma factory vendor with most competitive price

    Cas No: 958-09-8

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958-09-8 Usage

Description

2'-Deoxyadenosine is a natural deoxyribonucleoside, which is a structural fragment of deoxyribonucleic acid (DNA). It is a purine nucleoside component of DNA comprised of adenosine linked by its N9 nitrogen to the C1 carbon of deoxyribose. Like other natural nucleosides, it is involved in the transmission of genetic information in almost all biological cells, affecting protein synthesis and polysaccharide. It plays a very important role in regulating the growth, proliferation, differentiation, and inhibition of cells in vivo.

Uses

Used in Reproductive Biology:
2'-Deoxyadenosine is used as a sperm motility stimulant for paradoxical stimulation studies in human sperm motility. It plays an essential role in sperm micro-injection on mouse and human embryo development, contributing to the advancement of reproductive technologies.
Used in Cellular Energy Metabolism:
2'-Deoxyadenosine serves as an energy source in some cells under energy stress conditions, supporting cellular functions and survival during periods of metabolic stress.
Used in Biological Research:
2'-Deoxyadenosine is involved in various biological processes, allowing researchers to compare the functions of adenosine analogues. This contributes to a better understanding of the mechanisms of action and potential applications of related compounds in biological and medical research.

Preparation

2'-deoxyadenosine synthesis: esterification of adenosine, acylation of an acylating agent and an acid binding agent to obtain an acylate; the obtained acylate is then subjected to reduction and purification to obtain 2'-deoxyadenosine. The esterification agent used in the esterification process is dialkyl tin oxide, 2'-O-p-toluenesulfonyladenosine is synthesized from adenosine, and 2'-deoxyadenosine is synthesized from 2'-O-p-toluenesulfonyladenosine glycosides.

Biological Activity

2'-Deoxyadenosine is a deoxyribonucleoside and an intermediate in the purine nucleotide degradation pathway. It is transported into cells via facilitated diffusion or formed within cells by degradation of S-adenosylhomocysteine or AMP and is removed from cells by purine metabolism or is converted into adenine nucleotides. 2'-Deoxyadenosine has been used in the characterization of DNA conformations and the synthesis of nucleoside analogs as antiviral agents.

Check Digit Verification of cas no

The CAS Registry Mumber 958-09-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,5 and 8 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 958-09:
(5*9)+(4*5)+(3*8)+(2*0)+(1*9)=98
98 % 10 = 8
So 958-09-8 is a valid CAS Registry Number.

958-09-8 Well-known Company Product Price

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  • TCI America

  • (D4137)  2'-Deoxyadenosine Anhydrous  >98.0%(HPLC)(T)

  • 958-09-8

  • 5g

  • 1,250.00CNY

  • Detail

958-09-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 2'-deoxyadenosine

1.2 Other means of identification

Product number -
Other names Adenosine,2'-deoxy

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:958-09-8 SDS

958-09-8Synthetic route

Pyridine-2-carboxylic acid [9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-amide
661463-48-5

Pyridine-2-carboxylic acid [9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-amide

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With ammonia In water at 20℃; for 0.666667h;100%
magnesium hydroxide

magnesium hydroxide

2,3-dideoxy-α-D-ribose-1-phosphate

2,3-dideoxy-α-D-ribose-1-phosphate

2-deoxyribose-1-phosphate di(monocyclohexylammonium) salt

2-deoxyribose-1-phosphate di(monocyclohexylammonium) salt

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With sodium hydroxide In water99%
2'-iodo-2'-deoxyadenosine
59263-38-6

2'-iodo-2'-deoxyadenosine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With tris-(trimethylsilyl)silane; 2-hydroxyethanethiol In water at 100℃; for 4h;99%
5'-O-trityl-2'-deoxyadenosine
66503-49-9

5'-O-trityl-2'-deoxyadenosine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With silica gel; trifluoroacetic acid In methanol; chloroform96%
N6-(p-methoxybenzyl)-2'-deoxyadenosine

N6-(p-methoxybenzyl)-2'-deoxyadenosine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With ammonium peroxydisulfate; phosphate buffer at 80℃; for 2h;95%
Conditions
ConditionsYield
With potassium dihydrogenphosphate; Escherichia coli purine nucleoside phosphorylase In aq. buffer at 20℃; for 20h; pH=7.5; Enzymatic reaction;93%
With potassium dihydrogenphosphate; purine nucleoside phosphatase In water at 45℃; for 16h; pH 7.4;70%
2'-deoxy-3',5'-O-TIPDS-adenosine
258529-66-7

2'-deoxy-3',5'-O-TIPDS-adenosine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 5h;91.2%
2'-Deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine
84828-84-2

2'-Deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran90%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 75℃; for 1h;78%
With tetrabutyl ammonium fluoride Yield given;
With tetrabutyl ammonium fluoride In tetrahydrofuran at 70℃;
(-)-N6-(benzyl)-2'-deoxyadenosine
37113-47-6

(-)-N6-(benzyl)-2'-deoxyadenosine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With ammonium peroxydisulfate; phosphate buffer at 80℃; for 2h;88%
C24H30BN5O7

C24H30BN5O7

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With dihydrogen peroxide In aq. phosphate buffer; dimethyl sulfoxide at 20℃; for 0.333333h; pH=7.2;88%
Conditions
ConditionsYield
With nucleoside deoxyribosyltransferase-II; sodium citrate at 40℃; for 20h; pH=6.4; Enzymatic reaction;87%
With purine nucleoside phosphorylase; thymidine phosphorylase; phosphoric acid In aq. phosphate buffer at 37℃; for 24h; pH=6.8; Enzymatic reaction;
With recobinant purine nucleoside phosphorylase from Escherichia coli; recombinant thymidine phosphorylase from Escherichia coli In aq. phosphate buffer for 8h; pH=6.8; Catalytic behavior; Kinetics; Reagent/catalyst; Heating; Enzymatic reaction;
With Clostridium perfringens uridine phosphorylase; Aeromonas hydrophila purine nucleosidephosphorylase co-immobilized on glyoxyl-agarose In aq. phosphate buffer at 28℃; under 1034.32 Torr; pH=7.5; Flow reactor; Green chemistry; Enzymatic reaction;
2'-O-tosyladenosine
42776-78-3

2'-O-tosyladenosine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With lithium triethylborohydride In tetrahydrofuran at 0 - 5℃; for 3h; Solvent; Inert atmosphere;86.7%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 10h; Inert atmosphere;84.6%
C24H31N5O5
1427171-08-1

C24H31N5O5

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With ammonium hydroxide In water at 55℃; for 12h; Inert atmosphere;84%
N6-benzoyl-2'-deoxyadenosine
4546-72-9

N6-benzoyl-2'-deoxyadenosine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With ethylenediamine at 40℃; for 20h;83%
With ethylenediamine; phenol at 40℃; for 20h; debenzoylation;83%
With sodium hydroxide In methanol; water for 0.025h; microwave irradiation;
With ammonium hydroxide In water at 60℃; Rate constant;
With ammonium hydroxide at 55℃; for 5.5h;
2-deoxy–α-D-ribose 1-phosphate
17039-17-7

2-deoxy–α-D-ribose 1-phosphate

7H-purin-6-ylamine
73-24-5

7H-purin-6-ylamine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With purine nucleoside phosphorylase82%
N-6-methyl-2'-deoxyribofuranosil adenine
2002-35-9

N-6-methyl-2'-deoxyribofuranosil adenine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With manganese(IV) oxide; C17H20N4O9P(1-)*Na(1+); oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 7h; Irradiation; chemoselective reaction;79%
With Selectfluor; riboflavin In water; acetonitrile for 3h; Inert atmosphere; UV-irradiation;60%
With Selectfluor; riboflavin In water; acetonitrile at 37℃; under 760.051 Torr; for 3h; Inert atmosphere; Irradiation;60%
6-Chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine
91713-46-1

6-Chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With ammonia In methanol at 100℃; for 12h;78%
Conditions
ConditionsYield
With Enterobacter gergoviae CECT 875 in agarose In phosphate buffer at 60℃; for 1h; pH=7.0; Enzymatic reaction;77%
With Citrobacter koseri In aq. phosphate buffer at 60℃; for 1h; pH=7; Microbiological reaction;67%
With aeromonas hydrophila CECT 4221 at 60℃; for 4h; pH=7; aq. phosphate buffer; Enzymatic reaction;
C10H13N5O3S

C10H13N5O3S

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With nitric acid In water at 50℃; for 1h;76%
6-heptanoylamido-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-purine

6-heptanoylamido-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-purine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With sodium methylate In methanol at 20 - 45℃; for 1.16667h;73%
3'-O-TBDMS-5'-O-TBDPS-2'-deoxyadenosine
141479-79-0

3'-O-TBDMS-5'-O-TBDPS-2'-deoxyadenosine

A

3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine
51549-31-6

3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine

B

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With ammonium fluoride In methanol for 11h; Ambient temperature;A 72%
B 6%
7-methyl-2′-deoxyguanosine hydroiodide

7-methyl-2′-deoxyguanosine hydroiodide

A

7-methylguanine
578-76-7

7-methylguanine

B

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With potassium dihydrogenphosphate; purine nucleoside phosphatase In water at 45℃; for 16h; enzymatic synthesis of various β-D-ribo (and desoxyribo) nucleoside analogs; effect of temperature: 25-60 deg C;A n/a
B 70%

A

α-deoxyadenosine
3413-66-9

α-deoxyadenosine

B

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With ammonia In methanolA 62%
B 38%
With ammonia In methanol
methanol
67-56-1

methanol

2-bromo-2′-deoxyadenosine
89178-21-2

2-bromo-2′-deoxyadenosine

A

2'-deoxyspongosine
24757-70-8

2'-deoxyspongosine

B

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
for 0.5h; Irradiation;A 58%
B 15%
(1R)-S-ethyl-1-(6-amino-purin-9-yl)-1,4-anhydro-2-thio-D-arabitol
109285-09-8

(1R)-S-ethyl-1-(6-amino-purin-9-yl)-1,4-anhydro-2-thio-D-arabitol

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With sodium hydroxide; 2-methoxy-ethanol; nickel
2'-deoxyadenosine 3'-monophosphate
15731-72-3

2'-deoxyadenosine 3'-monophosphate

A

2'-deoxy-inosine
179112-93-7

2'-deoxy-inosine

B

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
mit Hilfe eines Enzym-Praeparats aus Darmschleimhaut;
2'-deoxyuridine
951-78-0

2'-deoxyuridine

7H-purin-6-ylamine
73-24-5

7H-purin-6-ylamine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With nucleoside-deoxyribosyltransferase Nucleosid-Desoxyribosyltransferase aus Lactobacillus helveticus;
2'-deoxy-inosine
179112-93-7

2'-deoxy-inosine

7H-purin-6-ylamine
73-24-5

7H-purin-6-ylamine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With nucleoside-deoxyribosyltransferase Nucleosid-Desoxyribosyltransferase aus Lactobacillus helveticus;
2'-Deoxyguanosine
961-07-9

2'-Deoxyguanosine

7H-purin-6-ylamine
73-24-5

7H-purin-6-ylamine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

Conditions
ConditionsYield
With nucleoside-deoxyribosyltransferase Nucleosid-Desoxyribosyltransferase aus Lactobacillus helveticus;
acetic anhydride
108-24-7

acetic anhydride

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

3',5'-di-O-acetyl-2'-deoxyadenosine
17318-24-0

3',5'-di-O-acetyl-2'-deoxyadenosine

Conditions
ConditionsYield
With pyridine; dmap for 4h; Ambient temperature;100%
With dmap; triethylamine In acetonitrile for 3h;90%
With pyridine85%
2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

2'-Deoxyadenosine N1-oxide
3506-01-2

2'-Deoxyadenosine N1-oxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In methanol Ambient temperature;100%
With 3-chloro-benzenecarboperoxoic acid In methanol for 5h; Ambient temperature;90%
With 3-chloro-benzenecarboperoxoic acid In methanol at 30℃; for 7h;
With 3-chloro-benzenecarboperoxoic acid In methanol; water for 16h; Ambient temperature;
Multi-step reaction with 2 steps
1: 78 percent / 1.) dinitrophenoxyamine, 2.) aq. HCl / dimethylformamide / 24 h / 37 °C
2: 84 percent / hydroxylamine, aq. NaOH / 48 h / 50 °C
View Scheme
2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

8-bromo-2'-deoxyadenosine
14985-44-5

8-bromo-2'-deoxyadenosine

Conditions
ConditionsYield
With bromine; sodium acetate; acetic acid In water at 20 - 50℃;100%
With bromine; sodium acetate88%
With sodium azide; bromoisocyanuric acid monosodium salt In water; N,N-dimethyl-formamide at 20℃; for 0.5h;88%
2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

2'-deoxy-8-deuteroadenosine
111915-85-6

2'-deoxy-8-deuteroadenosine

Conditions
ConditionsYield
With water-d2; triethylamine at 65℃; for 65h;100%
With [(2)H6]acetone; caesium carbonate In N,N-dimethyl-formamide at 80℃; for 1h;60%
With water-d2 at 90℃; for 5h; Substitution;
With water-d2 at 100℃; for 6h;
With water-d2; triethylamine
4,4'-dimethoxytrityl chloride
40615-36-9

4,4'-dimethoxytrityl chloride

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

N6-dimethoxytrityl-2'-deoxyadenosine
130999-19-8

N6-dimethoxytrityl-2'-deoxyadenosine

Conditions
ConditionsYield
With chloro-trimethyl-silane In pyridine at 20℃; for 16h;99%
Stage #1: 2'-deoxy-D-adenosine With pyridine; chloro-trimethyl-silane at 20℃; for 2h;
Stage #2: 4,4'-dimethoxytrityl chloride With pyridine at 20℃; for 16h;
99%
With chloro-trimethyl-silane Yield given. Multistep reaction;
With chloro-trimethyl-silane; ammonia 1.) pyridine, 15 min, 2.) pyridine, 18 h, room t., 3.) dioxane, water, 2 days; Yield given. Multistep reaction;
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

3',5'-bis-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine
51549-32-7

3',5'-bis-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;99%
With 1H-imidazole In N,N-dimethyl-formamide for 15h;98%
With 1H-imidazole In N,N-dimethyl-formamide at 35℃; for 16h;96%
2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

3',5'-O-(Di-tert-butylsilanediyl)deoxyadenosine
97204-91-6

3',5'-O-(Di-tert-butylsilanediyl)deoxyadenosine

Conditions
ConditionsYield
99%
m-trifluoromethylphenyl iodide
401-81-0

m-trifluoromethylphenyl iodide

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

8-(m-trifluoromethylphenyl)-2'-deoxyadenosine
1182278-93-8

8-(m-trifluoromethylphenyl)-2'-deoxyadenosine

Conditions
ConditionsYield
With piperidine; copper(l) iodide; palladium diacetate; caesium carbonate In N,N-dimethyl-formamide at 80℃; for 15h; Inert atmosphere;99%
Iodoacetic acid
64-69-7

Iodoacetic acid

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

C12H16N5O5(1+)

C12H16N5O5(1+)

Conditions
ConditionsYield
In aq. buffer at 60℃; for 8h; pH=7.0;99%
With sodium hydroxide In aq. phosphate buffer at 50℃; for 8h; pH=7;74.1%
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane
69304-37-6

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

2'-Deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine
84828-84-2

2'-Deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine

Conditions
ConditionsYield
With pyridine at 20℃; for 12h;98%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃;98%
With pyridine Ambient temperature;96%
benzoic acid anhydride
93-97-0

benzoic acid anhydride

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

N-benzoyl-3',5'-di-O-benzoyl-2'-deoxyadenosine
64723-02-0

N-benzoyl-3',5'-di-O-benzoyl-2'-deoxyadenosine

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.0266667h; microwave irradiation;98%
With dmap
chlorodimethyl(1,1,2-trimethylpropyl)silane
67373-56-2

chlorodimethyl(1,1,2-trimethylpropyl)silane

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

9-{(2R,4S,5R)-4-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-ylamine
187674-16-4

9-{(2R,4S,5R)-4-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-ylamine

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide98%
1-Chloro-4-iodobenzene
637-87-6

1-Chloro-4-iodobenzene

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

8-(4-chlorophenyl)-2'-deoxyadenosine
1252588-71-8

8-(4-chlorophenyl)-2'-deoxyadenosine

Conditions
ConditionsYield
With piperidine; copper(l) iodide; palladium diacetate; caesium carbonate In N,N-dimethyl-formamide at 80℃; for 15h; Sealed vessel;97%
mono-4-methoxytrityl chloride
14470-28-1

mono-4-methoxytrityl chloride

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

6-N-(4-Monomethoxytriphenylmethyl)-2'-deoxyadenosine
129789-01-1

6-N-(4-Monomethoxytriphenylmethyl)-2'-deoxyadenosine

Conditions
ConditionsYield
Stage #1: mono-4-methoxytrityl chloride; 2'-deoxy-D-adenosine With pyridine; chloro-trimethyl-silane at 0 - 20℃;
Stage #2: With ammonium hydroxide
96%
2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

deoxyinosine
890-38-0

deoxyinosine

Conditions
ConditionsYield
With adenosine deaminase for 1h; Ambient temperature;95%
With adenine deaminase from E. coli; water In aq. phosphate buffer at 25℃; pH=7.0; Catalytic behavior; Reagent/catalyst; Enzymatic reaction;
benzoyl chloride
98-88-4

benzoyl chloride

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

N6,N6-dibenzoyl-3′,5′-O-dibenzoyl-2′-deoxyadenosine
105791-57-9

N6,N6-dibenzoyl-3′,5′-O-dibenzoyl-2′-deoxyadenosine

Conditions
ConditionsYield
In pyridine at 65℃; for 4h;95%
N-Methyl-2,2-diethoxypyrrolidine
826-41-5

N-Methyl-2,2-diethoxypyrrolidine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

6-N-(N-methylpyrrolidin-2-ylidene)-2'-deoxyadenosine
88010-85-9

6-N-(N-methylpyrrolidin-2-ylidene)-2'-deoxyadenosine

Conditions
ConditionsYield
In pyridine at 25℃; for 16h;94%
benzoic acid
65-85-0

benzoic acid

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

N6-benzoyl-2'-deoxyadenosine
4546-72-9

N6-benzoyl-2'-deoxyadenosine

Conditions
ConditionsYield
Stage #1: benzoic acid With pyridine; 4-nitro-phenol; dicyclohexyl-carbodiimide; TEA In 1,4-dioxane at 20℃; for 2h;
Stage #2: 2'-deoxy-D-adenosine With pyridine; dicyclohexyl-carbodiimide In 1,4-dioxane at 0℃; for 2h;
94%
4-Iodobenzotrifluoride
455-13-0

4-Iodobenzotrifluoride

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

8-(p-trifluoromethylphenyl)-2'-deoxyadenosine
1182278-92-7

8-(p-trifluoromethylphenyl)-2'-deoxyadenosine

Conditions
ConditionsYield
With piperidine; copper(l) iodide; palladium diacetate; caesium carbonate In N,N-dimethyl-formamide at 80℃; for 15h; Inert atmosphere;94%
benzoyl cyanide
613-90-1

benzoyl cyanide

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

3',5'-di-O-benzoyl-2'-deoxyadenosine
20838-22-6

3',5'-di-O-benzoyl-2'-deoxyadenosine

Conditions
ConditionsYield
With pyridine; dmap at 40℃; for 6h;93%
With dmap; 1-ethylene glycol monomethyl ether-3-methylimidazolium methanesulfonate at 25 - 35℃;91%
With pyridine; dmap at 40℃; for 6h;93.0 % Chromat.
2-chloroethanal
107-20-0

2-chloroethanal

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

3-(2-Deoxy-β-D-erythro-pentafuranosyl)-3H-imidazo[2,1-i]purine
68498-25-9

3-(2-Deoxy-β-D-erythro-pentafuranosyl)-3H-imidazo[2,1-i]purine

Conditions
ConditionsYield
In water at 30℃; for 12h;92%
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 96h; pH=4 - 5;83%
Stage #1: 2'-deoxy-D-adenosine In water at 20℃; for 0.25h; pH=Ca. 7;
Stage #2: 2-chloroethanal With sodium hydroxide In water for 28h; pH=Ca. 4.2 - 4.5;
77%
vinyl acetate
108-05-4

vinyl acetate

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

5'-O-acetyl-2'-deoxyadenosine
72560-67-9

5'-O-acetyl-2'-deoxyadenosine

Conditions
ConditionsYield
With molecular sieve In tetrahydrofuran at 60℃; for 0.5h; Acetylation;92%
With Candida antarctica lipase acrylic resin In tetrahydrofuran at 60℃; for 1.5h;89%
dipalmitoylphosphatidylcholine
35418-55-4

dipalmitoylphosphatidylcholine

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

A

choline
62-49-7

choline

B

Hexadecanoic acid (S)-2-{[(2R,3S,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester
107110-41-8, 119067-13-9

Hexadecanoic acid (S)-2-{[(2R,3S,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester

Conditions
ConditionsYield
phospholipase D-P In chloroform at 45℃; for 6h; 100 mM acetate buffer (pH 4.0);A n/a
B 91%

958-09-8Relevant articles and documents

Prebiotic Photochemical Coproduction of Purine Ribo- And Deoxyribonucleosides

Xu, Jianfeng,Green, Nicholas J.,Russell, David A.,Liu, Ziwei,Sutherland, John D.

supporting information, p. 14482 - 14486 (2021/09/18)

The hypothesis that life on Earth may have started with a heterogeneous nucleic acid genetic system including both RNA and DNA has attracted broad interest. The recent finding that two RNA subunits (cytidine, C, and uridine, U) and two DNA subunits (deoxyadenosine, dA, and deoxyinosine, dI) can be coproduced in the same reaction network, compatible with a consistent geological scenario, supports this theory. However, a prebiotically plausible synthesis of the missing units (purine ribonucleosides and pyrimidine deoxyribonucleosides) in a unified reaction network remains elusive. Herein, we disclose a strictly stereoselective and furanosyl-selective synthesis of purine ribonucleosides (adenosine, A, and inosine, I) and purine deoxynucleosides (dA and dI), alongside one another, via a key photochemical reaction of thioanhydroadenosine with sulfite in alkaline solution (pH 8-10). Mechanistic studies suggest an unexpected recombination of sulfite and nucleoside alkyl radicals underpins the formation of the ribo C2′-O bond. The coproduction of A, I, dA, and dI from a common intermediate, and under conditions likely to have prevailed in at least some primordial locales, is suggestive of the potential coexistence of RNA and DNA building blocks at the dawn of life.

Thermodynamic Reaction Control of Nucleoside Phosphorolysis

Kaspar, Felix,Giessmann, Robert T.,Neubauer, Peter,Wagner, Anke,Gimpel, Matthias

, p. 867 - 876 (2020/01/24)

Nucleoside analogs represent a class of important drugs for cancer and antiviral treatments. Nucleoside phosphorylases (NPases) catalyze the phosphorolysis of nucleosides and are widely employed for the synthesis of pentose-1-phosphates and nucleoside analogs, which are difficult to access via conventional synthetic methods. However, for the vast majority of nucleosides, it has been observed that either no or incomplete conversion of the starting materials is achieved in NPase-catalyzed reactions. For some substrates, it has been shown that these reactions are reversible equilibrium reactions that adhere to the law of mass action. In this contribution, we broadly demonstrate that nucleoside phosphorolysis is a thermodynamically controlled endothermic reaction that proceeds to a reaction equilibrium dictated by the substrate-specific equilibrium constant of phosphorolysis, irrespective of the type or amount of NPase used, as shown by several examples. Furthermore, we explored the temperature-dependency of nucleoside phosphorolysis equilibrium states and provide the apparent transformed reaction enthalpy and apparent transformed reaction entropy for 24 nucleosides, confirming that these conversions are thermodynamically controlled endothermic reactions. This data allows calculation of the Gibbs free energy and, consequently, the equilibrium constant of phosphorolysis at any given reaction temperature. Overall, our investigations revealed that pyrimidine nucleosides are generally more susceptible to phosphorolysis than purine nucleosides. The data disclosed in this work allow the accurate prediction of phosphorolysis or transglycosylation yields for a range of pyrimidine and purine nucleosides and thus serve to empower further research in the field of nucleoside biocatalysis. (Figure presented.).

Solid-phase synthesis and structural characterisation of phosphoroselenolate-modified DNA: A backbone analogue which does not impose conformational bias and facilitates SAD X-ray crystallography

Conlon, Patrick F.,Eguaogie, Olga,Wilson, Jordan J.,Sweet, Jamie S. T.,Steinhoegl, Julian,Englert, Klaudia,Hancox, Oliver G. A.,Law, Christopher J.,Allman, Sarah A.,Tucker, James H. R.,Hall, James P.,Vyle, Joseph S.

, p. 10948 - 10957 (2019/12/23)

Oligodeoxynucleotides incorporating internucleotide phosphoroselenolate linkages have been prepared under solid-phase synthesis conditions using dimer phosphoramidites. These dimers were constructed following the high yielding Michaelis-Arbuzov (M-A) reaction of nucleoside H-phosphonate derivatives with 5′-deoxythymidine-5′-selenocyanate and subsequent phosphitylation. Efficient coupling of the dimer phosphoramidites to solid-supported substrates was observed under both manual and automated conditions and required only minor modifications to the standard DNA synthesis cycle. In a further demonstration of the utility of M-A chemistry, the support-bound selenonucleoside was reacted with an H-phosphonate and then chain extended using phosphoramidite chemistry. Following initial unmasking of methyl-protected phosphoroselenolate diesters, pure oligodeoxynucleotides were isolated using standard deprotection and purification procedures and subsequently characterised by mass spectrometry and circular dichroism. The CD spectra of both modified and native duplexes derived from self-complementary sequences with A-form, B-form or mixed conformational preferences were essentially superimposable. These sequences were also used to study the effect of the modification upon duplex stability which showed context-dependent destabilisation (-0.4 to-3.1 °C per phosphoroselenolate) when introduced at the 5′-Termini of A-form or mixed duplexes or at juxtaposed central loci within a B-form duplex (-1.0 °C per modification). As found with other nucleic acids incorporating selenium, expeditious crystallisation of a modified decanucleotide A-form duplex was observed and the structure solved to a resolution of 1.45 ?. The DNA structure adjacent to the modification was not significantly perturbed. The phosphoroselenolate linkage was found to impart resistance to nuclease activity.

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