5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose supplier

Name
5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose
EINECS
CAS No. 4613-71-2
Article Data3
CAS DataBase
Density
Solubility
Melting Point
Formula C16H18 O7
Boiling Point
Molecular Weight 322.315
Flash Point
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,2-Di-O-acetyl-5-O-benzoyl-3-deoxy-D-erythro-pentofuranose
PSA 88.13000
LogP 1.45320

Synthetic route

: 4105-29-7
[(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate

: 108-24-7
acetic anhydride

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

Conditions

Conditions	Yield
Stage #1: [(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate With acetic acid for 2h; Heating; Stage #2: acetic anhydride With pyridine; dmap at 20℃; Further stages.;	80%
With sulfuric acid In acetic acid	52%

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 7288-28-0
2,4-bis(trimethylsiloxy)-5-methylpyrimidine

: 143653-60-5
2'-O-acetyl-5'-O-benzoyl-3'-deoxy-5-methyluridine

Conditions

Conditions	Yield
With tin(IV) chloride In acetonitrile	93%

: 14631-20-0
4-N-Acetylcytosine

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 7057-33-2
3'-deoxycytidine

Conditions

Conditions	Yield
Stage #1: 4-N-Acetylcytosine; 5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose With benzenesulfonamide In acetonitrile for 1h; Heating; Stage #2: With trimethylsilyl trifluoromethanesulfonate at 20℃; for 5h; Stage #3: With ammonium hydroxide In tetrahydrofuran; methanol at 50℃; for 6h; Further stages.;	90%

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-erythro-pentofuranosyl azide

Conditions

Conditions	Yield
With trimethylsilylazide; tin(IV) chloride In dichloromethane at 23℃; for 12h; azidation;	74%

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 97626-98-7
N6-isobutyrylaminocytosine

: 159217-63-7
2'-O-Acetyl-5'-O-benzoyl-4-N-isobutyryl-3'-deoxycytidine

Conditions

Conditions	Yield
With tin(IV) chloride In 1,2-dichloro-ethane at 27℃; for 20h;	62%

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 1343405-24-2
C6H2ClN5

: 1343405-28-6
C20H16ClN5O5

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In acetonitrile for 1h; Reflux;	61%

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 4076-36-2
5-methyltetrazole

: Benzoic acid (2S,4R,5R)-4-acetoxy-5-(5-methyl-tetrazol-2-yl)-tetrahydro-furan-2-ylmethyl ester

Conditions

Conditions	Yield
In ethylenediamine for 48h;	54%

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 288-94-8
2H-tetrazole

: Benzoic acid (2S,4R,5R)-4-acetoxy-5-tetrazol-2-yl-tetrahydro-furan-2-ylmethyl ester

Conditions

Conditions	Yield
In ethylenediamine for 48h;	51%

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: N-(6,8-dioxo-7-(4-(trifluoromethyl)benzyl)-6,7,8,9-tetrahydro-1H-purin-2-yl)acetamide

: ((2S,4R,5R)-5-(2-acetamido-6,8-dioxo-7-(4-(trifluoromethyl)benzyl)-1,6,7,8-tetrahydro-9H purin-9-yl)-4-acetoxytetrahydrofuran-2-yl)methyl benzoate

Conditions

Conditions	Yield
Stage #1: 5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose; N-(6,8-dioxo-7-(4-(trifluoromethyl)benzyl)-6,7,8,9-tetrahydro-1H-purin-2-yl)acetamide With N,O-bis-(trimethylsilyl)-acetamide In 1,2-dichloro-ethane at 80℃; for 0.5h; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 3h;	11%

: 42890-94-8
(Ac)G(TMS)2

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

A: N2-acetyl-2'-O-acetyl-5'-O-benzoyl-3'-deoxyguanosine

B: Benzoic acid (2S,4R,5R)-4-acetoxy-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-7-yl)-tetrahydro-furan-2-ylmethyl ester

Conditions

Conditions	Yield
Yield given. Yields of byproduct given;

...Expand

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 18039-42-4
5-phenyl-2H-1,2,3,4-tetrazole

: Benzoic acid (2S,4R,5R)-4-acetoxy-5-(5-phenyl-tetrazol-2-yl)-tetrahydro-furan-2-ylmethyl ester

Conditions

Conditions	Yield
With tin(IV) chloride 1.) acetonitrile, 0 deg C, 1 h, 2.) 50 deg C, 2 h; Yield given. Multistep reaction;

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 306960-30-5
4-amino-8H-pyrido[2,3-d]pyrimidin-5-one

A: 1053253-53-4
benzoic acid 4-acetoxy-5-(4-amino-5-oxo-5H-pyrido[2,3-d]pyrimidin-8-yl)-tetrahydro-furan-2-ylmethyl ester

B: benzoic acid 4-acetoxy-5-(4-amino-5-oxo-5H-pyrido[2,3-d]pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Conditions

Conditions	Yield
Stage #1: 4-aminopyrido[2,3-d]pyrimidin-5(8H)-one With N,O-bis-(trimethylsilyl)-acetamide In 1,2-dichloro-ethane at 75℃; for 2h; Stage #2: 5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane for 72h; Vorbrueggen reaction; Heating; Further stages.;

...Expand

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 4-amino-5-oxo-8-(3-deoxy-β-D-ribofuranosyl)pyrido[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N,O-bis(trimethylsilyl)acetamide / 1,2-dichloro-ethane / 2 h / 75 °C 1.2: trimethylsilyl triflate / 1,2-dichloro-ethane / 72 h / Heating 2.1: NH3 / methanol / 20 h / 20 °C View Scheme

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: Benzoic acid (2S,4R,5S)-4-acetoxy-5-azido-tetrahydro-furan-2-ylmethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / Me3SiN3 / SnCl4 / CH2Cl2 / 12 h / 23 °C 2: SnCl4 / Me3SiOAc / CH2Cl2 / 192 h / 23 °C View Scheme

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 7057-33-2
3'-deoxycytidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 62 percent / SnCl4 / 1,2-dichloro-ethane / 20 h / 27 °C 2: 98 percent / NH3 / methanol / 12 h / 25 °C View Scheme

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 159217-64-8
4-(N-Isobutyryl)-3'-deoxycytidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 62 percent / SnCl4 / 1,2-dichloro-ethane / 20 h / 27 °C 2: 98 percent / NH3 / methanol / 12 h / 25 °C 3: 77 percent / dimethylformamide / 18 h / 25 °C View Scheme

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 159217-65-9
4-(N-Isobutyryl)-5'-O-(4,4'-dimethoxytrityl)-3'-deoxycytidine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 62 percent / SnCl4 / 1,2-dichloro-ethane / 20 h / 27 °C 2: 98 percent / NH3 / methanol / 12 h / 25 °C 3: 77 percent / dimethylformamide / 18 h / 25 °C 4: 84 percent / pyridine / 24 h / 25 °C View Scheme

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 4-(N-Isobutyryl)-5'-O-(4,4'-dimethoxytrityl)-3'-deoxycytidine 2'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 62 percent / SnCl4 / 1,2-dichloro-ethane / 20 h / 27 °C 2: 98 percent / NH3 / methanol / 12 h / 25 °C 3: 77 percent / dimethylformamide / 18 h / 25 °C 4: 84 percent / pyridine / 24 h / 25 °C 5: 86 percent / diisopropylammonium tetrazolide / CH2Cl2 / 7 h / 25 °C View Scheme

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 143653-61-6
3'-deoxy-5'-O-dimethoxytrityl-5-methyluridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 93 percent / SnCl4 / acetonitrile 2: 94 percent / K2CO3, MeOH / Heating 3: 81 percent / pyridine View Scheme

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 142103-12-6
Diisopropyl-phosphoramidous acid (2R,3R,5S)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 93 percent / SnCl4 / acetonitrile 2: 94 percent / K2CO3, MeOH / Heating 3: 81 percent / pyridine 4: 66 percent / iPr2NEt / tetrahydrofuran View Scheme

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 7084-29-9
3'-deoxy-5-methyluridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / SnCl4 / acetonitrile 2: 94 percent / K2CO3, MeOH / Heating View Scheme

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: C8H13N3O2Si

: 499785-77-2
{(2S,4R,5R)-4-(acetyloxy)-5-[3-(aminocarbonyl)-2-oxo-1(2H)-pyrazinyl]tetrahydro-2-furanyl}methyl benzoate

Conditions

Conditions	Yield
With tin(IV) chloride In acetonitrile at 20℃; for 0.5h;

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 30161-97-8
5-aminothaizolo<4,5-d>pyrimidine-2,7(3H,6H)-dione

: [(2S,4R,5R)-4-acetoxy-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-2-yl]methyl benzoate

Conditions

Conditions	Yield
Stage #1: 5-aminothiazolo<4,5-d>pyrimidine-2,7(3H,6H)-dione With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 20 - 70℃; for 0.5h; Inert atmosphere; Stage #2: 5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 70℃; for 14h; Inert atmosphere;	5.7 g

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 5-amino-3-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 20 - 70 °C / Inert atmosphere 1.2: 14 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / methanol / 3.5 h / 20 °C View Scheme

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: [(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]methyl benzoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 20 - 70 °C / Inert atmosphere 1.2: 14 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / methanol / 3.5 h / 20 °C View Scheme

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

5-amino-3-[(2R,3R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione: 5-amino-3-[(2R,3R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 20 - 70 °C / Inert atmosphere 1.2: 14 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / methanol / 3.5 h / 20 °C 3.1: 1H-imidazole / Petroleum ether; N,N-dimethyl-formamide / 2 h / 20 °C View Scheme

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: 5-amino-3-[(2R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-oxo-tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 20 - 70 °C / Inert atmosphere 1.2: 14 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / methanol / 3.5 h / 20 °C 3.1: 1H-imidazole / Petroleum ether; N,N-dimethyl-formamide / 2 h / 20 °C 4.1: Dess-Martin periodane / tetrahydrofuran / 2 h / 20 °C View Scheme

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: [(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-phenoxycarbothioyloxy-tetrahydrofuran-2-yl]methyl benzoate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 20 - 70 °C / Inert atmosphere 1.2: 14 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / methanol / 3.5 h / 20 °C 3.1: dmap / dichloromethane / 20 °C View Scheme

: 4613-71-2
5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

: [(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-(2-methylallyl)tetrahydrofuran-2-yl]methyl benzoate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 20 - 70 °C / Inert atmosphere 1.2: 14 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / methanol / 3.5 h / 20 °C 3.1: dmap / dichloromethane / 20 °C 4.1: 2,2'-azobis(isobutyronitrile) / toluene / 4 h / 80 °C / Inert atmosphere 4.2: 2 h / 20 °C / Inert atmosphere View Scheme

5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose Chemical Properties

Molecular Structure of 5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose (CAS NO.4613-71-2):

Systematic Name: D-Erythro-pentofuranose, 3-deoxy-, 1,2-diacetate 5-benzoate
Molecular Formula: C₁₆H₁₈O₇
Molecular Weight: 322.31
Mol File: 4613-71-2.mol
H bond acceptors: 7
H bond donors: 0
Freely Rotating Bonds: 8
Index of Refraction: 1.531
Molar Refractivity: 78.26 cm³
Molar Volume: 252.7 cm³
Surface Tension: 48 dyne/cm
Density: 1.27 g/cm³
Flash Point: 184.4 °C
Enthalpy of Vaporization: 67.36 kJ/mol
Boiling Point: 419.9 °C at 760 mmHg
Vapour Pressure: 2.94E-07 mmHg at 25 °C
SMILES: CC(=O)O[C@@H]1C[C@H](OC1OC(=O)C)COC(=O)c2ccccc2
InChI: InChI=1/C16H18O7/c1-10(17)21-14-8-13(23-16(14)22-11(2)18)9-20-15(19)12-6-4-3-5-7-12/h3-7,13-14,16H,8-9H2,1-2H3/t13-,14+,16?/m0/s1
InChIKey: DPLPHOLDKAGPOZ-NNKZFNQJBX

5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose Specification

5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose (CAS NO.4613-71-2), its Synonyms are D-erythro-Pentofuranose,3-deoxy-, 1,2-diacetate 5-benzoate ; 1,2-Di-O-acetyl-5-O-benzoyl-3-deoxy-D-erythro-pentofuranose ; 1,2-O-Di-O-acetyl-5-O-benzoyl-3-deoxy-D-ribofuranose .

Product Name

5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose

Synthetic route

5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose Chemical Properties

5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose Specification

Related Products

Hot Products