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33804

Sigma-Aldrich

1,3-Dibenzyloxy-2-propanol

purum, ≥97.0% (GC)

Synonym(s):

1,3-Bis(benzyloxy)-2-propanol, 1,3-Di-O-benzylglycerol

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About This Item

Linear Formula:
(C6H5CH2OCH2)2CHOH
CAS Number:
6972-79-8
Molecular Weight:
272.34
Beilstein/REAXYS Number:
1986774
MDL number:
MFCD00010616
UNSPSC Code:
12352100
PubChem Substance ID:
24860514

grade

purum

assay

≥97.0% (GC)

refractive index

n20/D 1.549 (lit.)
n20/D 1.549

bp

226-227 °C/3 mmHg (lit.)

density

1.103 g/mL at 20 °C (lit.)

SMILES string

OC(COCc1ccccc1)COCc2ccccc2

InChI

1S/C17H20O3/c18-17(13-19-11-15-7-3-1-4-8-15)14-20-12-16-9-5-2-6-10-16/h1-10,17-18H,11-14H2

InChI key

ARLSYSVVBAMYKA-UHFFFAOYSA-N

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Application

1,3-Dibenzyloxy-2-propanol was used as starting reagent in the synthesis of difluorinated cyclopropane nucleoside analogs possessing both two vicinal hydroxymethyl groups and a methylene spacer between the base and the ring. It was used as starting reagent in the synthesis of ganciclovir (GCV, 9-[(1,3-dihydroxy-2-propoxy)methyl]-guanine). It was also used in the synthesis of [3H] endocannabinoid 2-arachidonoylglycerol.

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M MacCarrone et al.
European journal of biochemistry, 268(3), 819-825 (2001-02-13)
The endocannabinoid 2-arachidonoylglycerol (2-Delta(4)Ach-Gro) activates human platelets in platelet-rich plasma at physiological concentrations. The activation was inhibited by selective antagonists of CB(1) and CB(2) cannabinoid receptors, but not by acetylsalicylic acid. Human platelets can metabolize 2-Delta(4)Ach-Gro by internalization through a
Preparation of novel difluorocyclopropane nucleosides.
Csuk R and Thiede G.
Tetrahedron, 55(3), 739-750 (1999)
Ji-Quan Wang et al.
Bioorganic & medicinal chemistry letters, 13(22), 3933-3938 (2003-11-01)
Positron emission tomography (PET) herpes simplex virus thymidine kinase (HSV-tk) gene reporter probes 9-[(3-[(18)F]fluoro-1-hydroxy-2-propoxy)methyl]guanine ([(18)F]FHPG) and 9-(4-[(18)F]fluoro-3-hydroxymethylbutyl)guanine ([(18)F]FHBG) were prepared by nucleophilic substitution of the appropriate tosylated precursors with [(18)F]KF/Kryptofix 2.2.2 followed by a quick deprotection reaction and purification with

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