tert-Butyl [(2R,3S)-1,3-dihydroxyoctadec-4-en-2-yl]carbamate
Basic information
- CAS
609812-03-5- Standard SMILES
CCCCCCCCCCCCCC=C[C@H](O)[C@@H](CO)NC(=O)OC(C)(C)C- InChIKey
UMUDVBSIURBUGW-RTWAWAEBSA-N- Molecular formula
- C23H45NO4
- Average molar mass
- 399.6 g/mol
- Monoisotopic mass
- 399.33485892
Names & identifiers
- Preferred name
- tert-Butyl [(2R,3S)-1,3-dihydroxyoctadec-4-en-2-yl]carbamate
- IUPAC
- tert-butyl N-[(2R,3S)-1,3-dihydroxyoctadec-4-en-2-yl]carbamate
- English name
- N-Boc-erythro-sphingosine
- Molecular formula
- C23H45NO4
- Molecular weight
- 399.61
Names & synonyms
tert-Butyl [(2R,3S)-1,3-dihydroxyoctadec-4-en-2-yl]carbamate609812-03-5N-Boc-erythro-sphingosinetert-butyl N-[(2R,3S)-1,3-dihydroxyoctadec-4-en-2-yl]carbamateDTXSID40849531(2S,3R,4E)-2-TERT-BUTYLOXYCARBONYLAMINO-4-OCTADECEN-1,3-DIOLCarbamic acid, N-[(1R,2S,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-, 1,1-dimethylethyl ester
Database identifiers
- CAS
609812-03-5- PubChem CID
- 71433697
- DTXSID
DTXSID40849531
Properties
Computed structural properties
- XLogP
- 6.9
- Topological polar surface area
- 78.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 18
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 404
Physicochemical properties
- Melting point
- 59 · 59-60°C
- Boiling point
- 536.574 · 536.574±50.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 0.975 · 0.975±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- storage temp.
- Refrigerator
- solubility
- Chloroform (Sparingly), Dichloromethane (Slightly), Ethyl Acetate (Slightly), Methane
- form
- Solid
- pka
- 11.53 · 11.530±0.46(predicted)
- color
- White
- Stability
- Freezer
Chemistry & industry
Applications
UsesThe N-Boc protected Sphingosine, a selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets; does not inhibit protein kinase A or myosin light chain kinase; inhibits calmodulin-dependent enzymes
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Compound notes
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