453455
(R)-(+)-Glycidyl trityl ether
98%, optical purity ee: 98% (GLC)
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About This Item
Empirical Formula (Hill Notation):
C22H20O2
CAS Number:
Molecular Weight:
316.39
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
InChI
1S/C22H20O2/c1-4-10-18(11-5-1)22(24-17-21-16-23-21,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15,21H,16-17H2/t21-/m1/s1
SMILES string
C1O[C@H]1COC(c2ccccc2)(c3ccccc3)c4ccccc4
InChI key
XFSXUCMYFWZRAF-OAQYLSRUSA-N
assay
98%
form
solid
optical activity
[α]20/D +10.5°, c = 1 in chloroform
optical purity
ee: 98% (GLC)
mp
99-102 °C (lit.)
Application
(R)-(+)-Glycidyl trityl ether may be used in the preparation of (R)-trityl(thiiranylmethyl)ether by reacting with thiourea. It may also be used as a starting material in the multi-step synthesis of (+)-actisonitrile.
Nucleotides with activity against herpes simplex virus 1 and 2, lipid ammonium salts, and thio analogs of phospholipids have been prepared recently through ring-opening of this epoxide with cytosine derivatives, amines, and thiols, respectively.
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Synthesis of aminoethanethiol trityl ether ligands for ruthenium-catalysed asymmetric transfer hydrogenation.
Harfouche J, et al.
Tetrahedron Letters, 15(21), 3413-3418 (2004)
Bennett, M.J. et al.
Tetrahedron Letters, 36, 2207-2207 (1995)
Lin, H.-K. Gelb, M.H.
Journal of the American Chemical Society, 115, 3932-3932 (1993)
Brodfuehrer, P.R. et al.
Tetrahedron Letters, 35, 3243-3243 (1994)
Structure and synthesis of a unique isonitrile lipid isolated from the marine mollusk Actinocyclus papillatus.
Manzo E, et al.
Organic Letters, 13(8), 1897-1899 (2011)
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