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540110

Sigma-Aldrich

(2R)-(−)-Glycidyl tosylate

98%

Synonym(s):

(R)-(−)-Glycidyl p-toluenesulfonate, (R)-(−)-Glycidyl tosylate, (R)-(−)-Oxirane-2-methanol p-toluenesulfonate salt

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About This Item

Empirical Formula (Hill Notation):
C10H12O4S
CAS Number:
113826-06-5
Molecular Weight:
228.26
Beilstein/REAXYS Number:
3592142
MDL number:
MFCD00010834
UNSPSC Code:
12352005
PubChem Substance ID:
24878442
NACRES:
NA.22

Quality Level

200

assay

98%

mp

46-49 °C (lit.)

storage temp.

2-8°C

SMILES string

Cc1ccc(cc1)S(=O)(=O)OC[C@H]2CO2

InChI

1S/C10H12O4S/c1-8-2-4-10(5-3-8)15(11,12)14-7-9-6-13-9/h2-5,9H,6-7H2,1H3/t9-/m1/s1

InChI key

NOQXXYIGRPAZJC-SECBINFHSA-N

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Application

(2R)-(-)-Glycidyl tosylate may be used to prepare:
  • 1-O-hexadecyl-sn-glycerol 3-O-p-toluenesulfonate by reacting with 1-hexadecanol in the presence of boron trifluoride etherate.
  • 4-Oxiranylmethoxy-(1H)-indole by reacting with 4-hydroxyindole in the presence of sodium hydride.
  • [18F]Epifluorohydin, an intermediate for preparing of [18F]fluoromisonidazole.
It can also be used as a starting material in the synthesis of 1,2-diacyl-sn-3-glycerophosphocholines.

Legal Information

Manufactured under license by Sterling Pharma Solutions Limited, using Jacobsen HKR technology.

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Danger

Hazard Classifications

Aquatic Chronic 2 - Carc. 1B - Eye Dam. 1 - Muta. 2 - Skin Sens. 1

wgk_germany

WGK 3

flash_point_f

>230.0 °F

flash_point_c

> 110 °C

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Facile diacylation of glycidyl tosylate. Chiral synthesis of symmetric-chain glycerophospholipids.
Ali S and Bittman R
The Journal of Organic Chemistry, 53(23), 5547-5549 (1988)
Isosteric phosphonate analogs of ET-16-OMe. Synthesis and biological evaluation of the enantiomers of 2'-(Trimethylammonio) ethyl 4-(hexadecyloxy)-3-methoxybutanephosphonate and 2'-(trimethylammonio) ethyl 4-(hexadecylthio)-3-methoxybutanephosphonate.
Bittman R, et al.
Journal of Medicinal Chemistry, 37(3), 425-430 (1994)
Novel aryloxy-8-azabicyclo [3.2. 1] oct-3-enes with 5-HT transporter and 5-HT 1A affinity.
Gilbert AM, et al.
Bioorganic & Medicinal Chemistry Letters, 14(21), 5281-5284 (2004)
A Radiosynthesis of fluorine-18.
Grierson JR, et al.
Journal of Nuclear Medicine, 30, 343-350 (1989)
Henry, N. et al.
Tetrahedron Letters, 45, 1465-1465 (2004)

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