(S)-Pro-xylane CAS#: 868156-46-1; ChemWhat Code: 1417895

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product Name(S)-Pro-xylane
IUPAC Name
Molecular Structure Structure of (S)-Pro-xylane CAS# 868156-46-1
CAS Registry Number868156-46-1
EINECS Number
MDL NumberMFCD32701904
Beilstein Registry Number
Synonyms
Molecular FormulaC8H16O5
Molecular Weight192.210
InChI
InChI Key
Canonical SMILES
Patent Information
Patent IDTitlePublication Date
US2005/250708Novel C-glycosides, uses thereof2005

Physical Data

AppearanceSolid
Melting Point, °C
120 – 122

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)
Chemical shifts, Spectrum1Hwater-d2
Chemical shifts, Spectrum13Cwater-d2
Chemical shifts1H
Chemical shifts13C
Chemical shifts1HCD3OD

Route of Synthesis (ROS)

Route of Synthesis (ROS) of (S)-Pro-xylane CAS# 868156-46-1
Route of Synthesis (ROS) of (S)-Pro-xylane CAS# 868156-46-1
ConditionsYield
With sodium tris(acetoxy)borohydride In isopropyl alcohol at 20℃; Product distribution / selectivity;

Experimental Procedure
2 Production of C-β-D-xylopyranoside-2-(S)-hydroxypropane
EXAMPLE 2 Production of C-β-D-xylopyranoside-2-(S)-hydroxypropane The expected compound was obtained according the process described in Example 1, replacing the 2 ml of acetic acid and the sodium borohydride with two times 1.2 equivalents of sodium triacetoxyborohydride (NaBH(OAc)3). The product was obtained with a quantitative yield, and selectively in (β, S) form. The physico chemical characteristics are identical in all respects to those obtained in Example 1.
100%
With sodium tetrahydroborate; acetic acid In isopropyl alcohol at 20℃; for 1.5h; Product distribution / selectivity;

Experimental Procedure
1 Production of C-β-D-xylopyranoside-2-(S)-hydroxypropane
EXAMPLE 1 Production of C-β-D-xylopyranoside-2-(S)-hydroxypropane 2 ml of acetic acid, followed rapidly by 120 mg (1.2 eq.) of sodium borohydride as granules were added to a solution of 500 mg of C-β-D-xylopyranoside-2-propanone (described in Example 1 of application WO-02/051828) in 9 ml of isopropanol. The medium was left at ambient temperature for 30 minutes with stirring. 120 mg (1.2 eq.) of sodium borohydride as granules were then added. The reaction medium was left for 1 hour at ambient temperature with stirring. 10 ml of acetone were then added and, after stirring for 30 minutes at ambient temperature, the reaction medium was concentrated under vacuum. The residue obtained was purified by silica gel chromatography so as to selectively produce the expected compound C-β-D-xylopyranoside-2-(S)-hydroxypropane with a 95% yield. Physico chemical characteristics of the compound: Melting point: 120-122° C. Optical rotation: -37° (at 20° C. in methanol, and at a concentration [C]=1 g/100 ml) 1H NMR: 1.03 (t, 3H); 1.46 (m, 1H); 1.71 (m, 1H); 2.85 (m, 1H); 2.94 (m, 1H); 2.99 (m, 2H); 3.24 (m, 1H); 3.67 (m, 1H); 3.77 (m, 1H) Structure confirmed by X-ray diffraction.
95%

Safety and Hazards

Pictogram(s)
Signal
GHS Hazard StatementsNot Classified
Precautionary Statement Codes

Other Data

Druglikeness
Lipinski rules component
Molecular Weight192.212
logP-1.202
HBA5
HBD4
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)90.15
Rotatable Bond (RotB)2
Matching Veber Rules2
Use Pattern
Anti-aging, promotes skin cell renewal, helps repair and rebuild the skin’s collagen and glycosaminoglycans, thereby reducing wrinkles and fine lines. Moisturizing and nourishing, promotes the synthesis of collagen, repairs damaged skin; enhances overall skin health.

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