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453455

Sigma-Aldrich

(R)-(+)-Glycidyl trityl ether

98%, optical purity ee: 98% (GLC)

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About This Item

Empirical Formula (Hill Notation):
C22H20O2
CAS Number:
65291-30-7
Molecular Weight:
316.39
MDL number:
MFCD00273368
UNSPSC Code:
12352005
PubChem Substance ID:
24868810
NACRES:
NA.22

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.)

SMILES string

C1O[C@H]1COC(c2ccccc2)(c3ccccc3)c4ccccc4

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

InChI key

XFSXUCMYFWZRAF-OAQYLSRUSA-N

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 Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
05416KQ
05024KI

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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)
Lin, H.-K. Gelb, M.H.
Journal of the American Chemical Society, 115, 3932-3932 (1993)
Bennett, M.J. et al.
Tetrahedron Letters, 36, 2207-2207 (1995)
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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