59278-00-1

Basic information

• Product Name: 2-[(Acetyloxy)methoxy]ethyl acetate
• Synonyms: 2-[(Acetyloxy)methoxy]ethyl acetate;1,4-DIACETOXY-2-OXABUTANE;2-Oxo-1,4-Butanediol Diacetate;(2-Acetoxyethoxy)methylacetate;2-Acetoxyethyl acetoxymethyl ethe;Acecloguanosine lateral chain;2-Acetoxyethyl acetoxymethyl ether;2-[(Acetyloxy)methoxy]ethanol acetate
• CAS NO: 59278-00-1
• Molecular Formula: C₇H₁₂O₅
• Molecular Weight: 176.17
• EINECS: 261-686-7
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 59278-00-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 114-1180C/4Torr
• Flash Point: 90.9 °C
• Appearance: clear, colourless or yellowish liquid
• Density: 1.119 g/cm³
• Vapor Pressure: 0.0874mmHg at 25°C
• Refractive Index: 1.4210 to 1.4250
• Storage Temp.: Sealed in dry,Room Temperature
• Stability: Below 40C
• CAS DataBase Reference: 2-[(Acetyloxy)methoxy]ethyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(Acetyloxy)methoxy]ethyl acetate(59278-00-1)
• EPA Substance Registry System: 2-[(Acetyloxy)methoxy]ethyl acetate(59278-00-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 59278-00-1(Hazardous Substances Data)

Usage

Chemical Properties

Bright Yellow Liquid

Uses

Different sources of media describe the Uses of 59278-00-1 differently. You can refer to the following data:
1. Intermediate for the preparation of Acyclovir-d4
2. Intermediate for the preparation of Acyclovir-d4.

InChI:InChI=1/C7H12O5/c1-6(8)11-4-3-10-5-12-7(2)9/h3-5H2,1-2H3

Synthetic route

1,3-epoxycyclopentane + acetic anhydride (108-24-7) → 2-acetoxyethyl acetoxymethyl ether (59278-00-1)

Conditions	Yield
With toluene-4-sulfonic acid at 35 - 40℃; for 0.833333h; Reagent/catalyst; Temperature;	91%

1,3-DIOXOLANE (646-06-0) + Acetyl bromide (506-96-7) + sodium acetate (127-09-3) → 2-acetoxyethyl acetoxymethyl ether (59278-00-1)

Conditions	Yield
Stage #1: 1,3-DIOXOLANE; Acetyl bromide Stage #2: sodium acetate With acetic acid at 110℃; for 1h;	77%

1,3-DIOXOLANE (646-06-0) + acetic anhydride (108-24-7) → 2-acetoxyethyl acetoxymethyl ether (59278-00-1)

Conditions	Yield
With sulfuric acid Ambient temperature;	74%
With sulfuric acid at -5 - 20℃;	52%
With iron(III) chloride

1,3-DIOXOLANE (646-06-0) + Acetyl bromide (506-96-7) → 2-acetoxyethyl acetoxymethyl ether (59278-00-1)

Conditions	Yield
With sodium acetate In acetic acid at 110℃; for 1h;	60%

1,3-DIOXOLANE (646-06-0) + sulfuric acid (7664-93-9) + sodium acetate (127-09-3) + acetic anhydride (108-24-7) → ethylene glycol diacetate (111-55-7) + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 1,2-bis(acetoxy-methyloxy)ethane (90114-17-3)

1,3-DIOXOLANE (646-06-0) + acetic anhydride (108-24-7) → 2-acetoxyethyl acetoxymethyl ether (59278-00-1) + ethylene glycol diacetat; ethylene glycol-bis-acetoxymethyl ether

Conditions	Yield
With sulfuric acid at 20℃; Versetzen des abgekuehlten Reaktionsgemisches mit Natriumacetat;

N2-acetyl-7-benzylguanine (17495-10-2) → 9-(2-acetoxyethoxy)methyl-7-benzyl-N2-acetylguaninium acetate + 2-acetoxyethyl acetoxymethyl ether (59278-00-1)

Conditions	Yield
In N,N-dimethyl-formamide

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 2,9-diacetylguanine (3056-33-5) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3)

Conditions	Yield
at 105℃; for 80h;	95.1%
With toluene-4-sulfonic acid In toluene at 110℃; Temperature; Large scale;	94.3%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 6-benzyladenine (1214-39-7) → 9-<(2-acetoxyethoxy)methyl>-6-benzylaminopurine (173205-63-5)

Conditions	Yield
With aluminum oxide; silica gel for 0.0666667h; microwave irradiation;	95%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 5-Methylimidazo<4,5-d><1,3>thiazine-7(3H)-thione (126094-26-6) → 3-(2-Acetoxyethoxymethyl)-5-methylimidazo<4,5-d><1,3>thiazine-7(3H)-thione (136369-77-2)

Conditions	Yield
at 150℃; for 0.333333h;	94%

diacetyl guanine + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3)

Conditions	Yield
In methanol; dichloromethane	94%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 6-chloropurine (87-42-3) → 9-<(2-acetoxyethoxy)methyl>-6-chloropurine (81777-47-1)

Conditions	Yield
With aluminum oxide; silica gel for 0.0666667h; microwave irradiation;	93%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + trimethylsilylated 2-thioadenine → 9-(2-acetoxyethoxy methyl)-2-thioadenine (116457-82-0)

Conditions	Yield
cesium iodide In acetonitrile for 2h; Heating;	92%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 6-(3,5-dimethylbenzyl)-5-ethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (171048-65-0) → 1-(2-acetoxyethoxymethyl)-6-(3,5-dimethylbenzyl)-5-ethyluracil (444788-50-5)

Conditions	Yield
Stage #1: 2-acetoxyethyl acetoxymethyl ether; 6-(3,5-dimethylbenzyl)-5-ethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione With chloro-trimethyl-silane; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 14.3333h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water	92%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 2,4,6-tris(trimethylsilyloxy)pyrimidine (31111-39-4) → 1-<(2-acetoxyethoxy)methyl>barbituric acid (154021-74-6)

Conditions	Yield
With tin(IV) chloride In dichloromethane at 18 - 25℃;	91%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 2,6 dichloropurine (5451-40-1) → 9-<(2-acetoxyethoxy)methyl>-2,6-dichloropurine (59277-99-5)

Conditions	Yield
With aluminum oxide; silica gel for 0.1h; microwave irradiation;	91%

diacetylguanine + diacetyl guanine + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3)

Conditions	Yield
In methanol; toluene	91%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N4-benzoylcytosine (69304-43-4) → 1-{2-O-[(2-acetoxyethoxy)methyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl}-N4-benzoylcytosine (933063-81-1)

Conditions	Yield
With tin(IV) chloride In 1,2-dichloro-ethane at -12℃; for 0.333333h;	87%
With tin(IV) chloride In 1,2-dichloro-ethane at -12℃; for 0.333333h;

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + acetic anhydride (108-24-7) + G (118-00-3) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine (91702-60-2)

Conditions	Yield
With toluene-4-sulfonic acid at 100℃; for 20h;	A 86% B 0.5%
With sulfuric acid at 100℃; for 24h; Product distribution; other acid caclysts, temperature time, solvents; transpurination reaction of guanosine under various conditions;	A 43% B 35%
With phosphoric acid at 100℃; for 24h; Title compound not separated from byproducts;	A 47 % Chromat. B 38 % Chromat.

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (69304-38-7) → 1-{2-O-[(2-acetoxyethoxy)methyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl}uracil (933063-80-0)

Conditions	Yield
With tin(IV) chloride In 1,2-dichloro-ethane at -12℃; for 0.333333h;	86%
With tin(IV) chloride In 1,2-dichloro-ethane at -12℃; for 0.333333h;
With tin(IV) chloride In dichloromethane at -12℃; for 0.333333h;

5-bromouracil (51-20-7) + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) → 1-<(2-acetoxyethoxy)methyl>-5-bromouracil (78692-73-6)

Conditions	Yield
Stage #1: 5-bromouracil With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 15h; Stage #2: 2-acetoxyethyl acetoxymethyl ether With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 24h;	85%
With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; zinc(II) iodide 1.) DMF, 100 deg C, 7 h; Yield given. Multistep reaction;

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + N-phenyl-9H-purin-6-amine (1210-66-8) → 9-[(2-acetoxyethoxy)methyl]-6-phenylaminopurine

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	85%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → 1-<(2-acetoxyethoxy)methyl>thymine (81777-42-6)

Conditions	Yield
With ammonium sulfate; isocyanate de chlorosulfonyle In acetonitrile for 2h; Heating;	83%
With 1,1,1,3,3,3-hexamethyl-disilazane; potassium iodide-doped natural phosphate	45%
natural phosphate In acetonitrile for 3h; Heating;
iodine-doped natural phosphate In acetonitrile Heating;

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 2-chloro-N-phenyl-9H-purin-6-amine (185408-97-3) → 9-[(2-acetoxyethoxy)methyl]-2-chloro-6-phenylaminopurine

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	83%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + N6-Cyclohexyladenine (7674-45-5) → 9-[(2-acetoxyethoxy)methyl]-6-cyclohexylaminopurine

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	82%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 6-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-7-one (1225549-78-9) → 3-[(2-acetoxyethoxy)methyl]-6-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-7-one (1542213-33-1) + 4-[(2-acetoxyethoxy)methyl]-6-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-7-one (1542213-35-3)

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 3h; Reagent/catalyst; Solvent; Temperature; Time; Vorbrueggen Nucleoside Synthesis;	A 2% B 82%
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 0.2h; Vorbrueggen Nucleoside Synthesis; Overall yield = 48 %;	A 36% B 12%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)indazole (52562-51-3, 63202-26-6, 73370-77-1, 73370-78-2, 73370-81-7, 73370-82-8, 73370-85-1, 73370-86-2) → 1-<(2-acetoxyethyl)methyl>indazole (162894-30-6)

Conditions	Yield
With toluene-4-sulfonic acid In chlorobenzene at 130℃; for 0.25h;	81%

(2-chloro-9H-purin-6-yl)-cyclohexyl-amine (39639-45-7) + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) → 9-[(2-acetoxyethoxy)methyl]-2-chloro-6-cyclohexylaminopurine

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	81%

3-oxo-3,4-dihydropyrazine-2-carboxamide (55321-99-8) + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) → 2-((3-carbamoyl-2-oxopyrazin-1(2H)-yl) methoxy) ethyl acetate

Conditions	Yield
Stage #1: 3-oxo-3,4-dihydropyrazine-2-carboxamide With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 1h; Inert atmosphere; Reflux; Stage #2: 2-acetoxyethyl acetoxymethyl ether With tin(IV) chloride In acetonitrile at 20℃; Inert atmosphere; Cooling with ice;	81%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 6-benzyl-5-but-2-enyl-1H-pyrimidine-2,4-dione (486999-72-8) → 1-((2-acetoxyethoxy)methyl)-6-benzyl-5-(2-butenyl)-1H-pyrimidine-2,4-dione (486999-81-9)

Conditions	Yield
Stage #1: 2-acetoxyethyl acetoxymethyl ether; 6-benzyl-5-but-2-enyl-1H-pyrimidine-2,4-dione With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane Stage #2: With tin(IV) chloride In dichloromethane at 0 - 20℃;	80%

(7(9)H-purin-6-yl)-p-tolyl-amine (5446-36-6) + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) → 9-[(2-acetoxyethoxy)methyl]-6-(p-tolylamino)purine

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	80%

N-(4-methoxyphenyl)-9H-purine-6-amine + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) → 9-[(2-acetoxyethoxy)methyl]-6-(p-methoxyphenylamino)purine

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	80%

(4-ethoxy-phenyl)-(9H-purin-6-yl)-amine + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) → 9-[(2-acetoxyethoxy)methyl]-6-(p-ethoxyphenylamino)purine

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	79%

2-chloro-6-(4-methylphenyl)amino-9H-purin (39639-49-1) + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) → 9-[(2-acetoxyethoxy)methyl]-2-chloro-6-(p-tolylamino)purine

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	78%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 5-(3-isopropyl-adamantan-1-yl)-2,4-bis-trimethylsilanyloxy-pyrimidine (263239-79-8) → acetic acid 2-[5-(3-isopropyl-adamantan-1-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy]-ethyl ester (263239-81-2)

Conditions	Yield
With tin(IV) chloride In dichloromethane for 3h; Alkylation; Heating;	77%

Upstream product

• 646-06-0 1,3-DIOXOLANE 
• 506-96-7 Acetyl bromide 
• 7664-93-9 sulfuric acid 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 17495-10-2 N²-acetyl-7-benzylguanine 

Downstream Products

• 77474-49-8 1-<(2-acetoxyethoxy)methyl>-5-fluorouracil 
• 75128-73-3 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one 
• 91702-60-2 7-<(2-acetoxyethoxy)methyl>-N²-acetylguanine 
• 102728-64-3 9-[(acetoxyethoxy)methyl]guanine 
• 136369-66-9 1-(2-Acetoxyethoxymethyl)-5-phenylimidazo<4,5-d><1,3>thiazine-7(1H)-thione 
• 136369-65-8 3-(2-Acetoxyethoxymethyl)-5-phenylimidazo<4,5-d><1,3>thiazine-7(3H)-thione 
• 136369-78-3 3-(2-Acetoxyethoxymethyl)-5-benzylaminoimidazo<4,5-d><1,3>thiazine-7(3H)-thione 
• 118380-80-6 5-benzyl-1-(2-acetoxyethoxymethyl)uracil 
• 118380-81-7 5-benzyl-3-(2-acetoxyethoxymethyl)uracil 
• 118380-82-8 5-benzyl-3,5-bis(2-acetoxyethoxymethyl)uracil 
• 102728-66-5 7-(2-acetoxyethoxymethyl)-2-aminopurin-6-one 
• 1026644-82-5 Acetic acid 2-(2,4-dioxo-7-phenyl-3,4-dihydro-2H-thieno[3,2-d]pyrimidin-1-ylmethoxy)-ethyl ester 
• 1026608-51-4 Acetic acid 2-(2,4-dioxo-7-p-tolyl-3,4-dihydro-2H-thieno[3,2-d]pyrimidin-1-ylmethoxy)-ethyl ester 
• 1026704-20-0 Acetic acid 2-[7-(4-fluoro-phenyl)-2,4-dioxo-3,4-dihydro-2H-thieno[3,2-d]pyrimidin-1-ylmethoxy]-ethyl ester 

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