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22224-41-5 molecular structure
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(2R,3R,4S,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-3-hydroxyoxolan-2-yl benzoate

ChemBase ID: 104016
Molecular Formular: C26H22O8
Molecular Mass: 462.44808
Monoisotopic Mass: 462.13146766
SMILES and InChIs

SMILES:
O=C(O[C@H]1O[C@@H]([C@@H](OC(=O)c2ccccc2)[C@H]1O)COC(=O)c1ccccc1)c1ccccc1
Canonical SMILES:
O[C@H]1[C@H](O[C@@H]([C@H]1OC(=O)c1ccccc1)COC(=O)c1ccccc1)OC(=O)c1ccccc1
InChI:
InChI=1S/C26H22O8/c27-21-22(33-24(29)18-12-6-2-7-13-18)20(16-31-23(28)17-10-4-1-5-11-17)32-26(21)34-25(30)19-14-8-3-9-15-19/h1-15,20-22,26-27H,16H2/t20-,21-,22-,26-/m1/s1
InChIKey:
HUHVPBKTTFVAQF-PIXQIBFHSA-N

Cite this record

CBID:104016 http://www.chembase.cn/molecule-104016.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R,3R,4S,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-3-hydroxyoxolan-2-yl benzoate
[(2R,3S,4R,5R)-3,5-bis(benzoyloxy)-4-hydroxyoxolan-2-yl]methyl benzoate
(2R,3S,4R,5R)-5-(benzoyloxy)-2-[(benzoyloxy)methyl]-4-hydroxyoxolan-3-yl benzoate
IUPAC Traditional name
(2R,3R,4S,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-3-hydroxyoxolan-2-yl benzoate
[(2R,3S,4R,5R)-3,5-bis(benzoyloxy)-4-hydroxyoxolan-2-yl]methyl benzoate
(2R,3S,4R,5R)-5-(benzoyloxy)-2-[(benzoyloxy)methyl]-4-hydroxyoxolan-3-yl benzoate
Synonyms
alpha-D-Ribofuranose 1,3,5-tribenzoate
1,3,5-Tri-O-benzoyl-alpha-D-ribofuranose
1,3,5-Tri-O-benzoyl-α-D-ribofuranose
α-D-Ribofuranose 1,3,5-tribenzoate
α-D-Ribofuranose 1,3,5-tribenzoate
1,3,5-TRI-O-BENZOYL-α-D-RIBOFURANOSE
1,3,5-三-O-苯甲酰-α-D-呋喃核糖
α-D-呋喃核糖 1,3,5-三苯甲酯
CAS Number
22224-41-5
MDL Number
MFCD00080818
Beilstein Number
98446
PubChem SID
24864261
24889390
162090993
PubChem CID
11005061

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.318027  H Acceptors
H Donor LogD (pH = 5.5) 5.1836953 
LogD (pH = 7.4) 5.18369  Log P 5.1836953 
Molar Refractivity 119.4269 cm3 Polarizability 47.08571 Å3
Polar Surface Area 108.36 Å2 Rotatable Bonds 10 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
125-129 °C(lit.) expand Show data source
125-129°C expand Show data source
Optical Rotation
[α]20/D +85.0°, c = 1 in chloroform expand Show data source
[α]20/D +86±2°, c = 1% in chloroform expand Show data source
+85 (c=1 in chloroform) expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥97.0% (TLC) expand Show data source
97% expand Show data source
Grade
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C26H22O8 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 389080 external link
Packaging
5 g in glass bottle
Application
Starting material for nucleosides.1,2
Sigma Aldrich - 90650 external link
Other Notes
Building block for preparing 2′-deoxy and 2′-O-substituted nucleosides1,2,3

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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