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13242-55-2 molecular structure
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(2R,3S,4R,5R)-2,3-bis(acetyloxy)-6,8-dioxabicyclo[3.2.1]octan-4-yl acetate

ChemBase ID: 160675
Molecular Formular: C12H16O8
Molecular Mass: 288.25064
Monoisotopic Mass: 288.08451747
SMILES and InChIs

SMILES:
[C@@H]1([C@@H]([C@@H]([C@H]2OC1CO2)OC(=O)C)OC(=O)C)OC(=O)C
Canonical SMILES:
CC(=O)O[C@H]1[C@H](OC(=O)C)C2CO[C@@H]([C@H]1OC(=O)C)O2
InChI:
InChI=1S/C12H16O8/c1-5(13)17-9-8-4-16-12(20-8)11(19-7(3)15)10(9)18-6(2)14/h8-12H,4H2,1-3H3/t8?,9-,10+,11-,12-/m1/s1
InChIKey:
BAKQMOSGYGQJOJ-UPUXHGCUSA-N

Cite this record

CBID:160675 http://www.chembase.cn/molecule-160675.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R,3S,4R,5R)-2,3-bis(acetyloxy)-6,8-dioxabicyclo[3.2.1]octan-4-yl acetate
IUPAC Traditional name
(2R,3S,4R,5R)-2,3-bis(acetyloxy)-6,8-dioxabicyclo[3.2.1]octan-4-yl acetate
Synonyms
2,3,4-Tri-O-acetyl-1,6-anhydro-β-D-glucopyranose
Triacetyllevoglucosan
NSC 25284
1,6-Anhydro-β-D-glucopyranose 2,3,4-Triacetate
CAS Number
13242-55-2
PubChem SID
162254810
PubChem CID
71313422

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC A648200 external link Add to cart
PubChem 71313422 external link
Data Source Data ID Price
TRC
A648200 external link Add to cart Please log in.
Data Source Data ID
PubChem 71313422 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) -0.44745943  LogD (pH = 7.4) -0.44745943 
Log P -0.44745943  Molar Refractivity 59.8678 cm3
Polarizability 25.374388 Å3 Polar Surface Area 97.36 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
108-109°C expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
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DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - A648200 external link
1,6-Anhydrohexopyranoses have proven to be valuable synthons for the preparation of biologically important and structurally diverse products (e.g. rifamycin S, indanomycin, thromboxane B2, (+)-biotin, tetrodotoxin, quinone, and macrolide antibiotics) as

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Fraser-Reid, B., et al. J. Am. Chem. Soc. 106, 731 (1984)
  • • Edwards, M.P., et al. J. Org. Chem. 49, 3503 (1984)
  • • Kelly, A.G., and Roberts, J.S. J. Chem. Soc., Chem. Commun. 228, (1984)
  • • Ogawa, T., et al. Carbohydr. Res. 57, C31 (1984)
  • • Isobe, M., et al. Te
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PATENTS

PATENTS

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INTERNET

INTERNET

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