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Basic Information
CAS No.: 4613-71-2
Name: 5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose
Molecular Structure:
Molecular Structure of 4613-71-2 (5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose)
Formula: C16H18 O7
Molecular Weight: 322.315
Synonyms: 1,2-Di-O-acetyl-5-O-benzoyl-3-deoxy-D-erythro-pentofuranose
PSA: 88.13000
LogP: 1.45320
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Synthetic route
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4613-71-2

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

Conditions
ConditionsYield
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 acid52%
4613-71-2

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

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Conditions
ConditionsYield
With tin(IV) chloride In acetonitrile93%
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4-N-Acetylcytosine

4613-71-2

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

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Conditions
ConditionsYield
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
ConditionsYield
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

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N6-isobutyrylaminocytosine

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2'-O-Acetyl-5'-O-benzoyl-4-N-isobutyryl-3'-deoxycytidine

Conditions
ConditionsYield
With tin(IV) chloride In 1,2-dichloro-ethane at 27℃; for 20h;62%
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5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose

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C6H2ClN5

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C20H16ClN5O5

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
Yield given. Yields of byproduct given;
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Chemistry

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

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 .