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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

453455-BULK:
453455-VAR:
453455-1G:
453455-5G:

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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)
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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