Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate
Need Assistance?
  • US & Canada:
    +
  • UK: +

Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

A peptide coupling reagent. It can be used in the preparation of phenyl esters of amino acids which have been shown to be valuable as blocked derivatives of amino acids in the field of peptide synthesis.

Category
Peptide Synthesis Reagents
Catalog number
BAT-002395
CAS number
56602-33-6
Molecular Formula
C12H22F6N6OP2
Molecular Weight
442.28
Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate
IUPAC Name
benzotriazol-1-yloxy-tris(dimethylamino)phosphanium;hexafluorophosphate
Synonyms
Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate; Bop reagent; ((1H-Benzo[d][1,2,3]triazol-1-yl)oxy)tris(dimethylamino)phosphonium hexafluorophosphate(V); Castro's Reagent; CCRIS 2602; Tri(dimethylamino)benzotriazol-1-yloxyphosphonium hexafluorophosphate; EINECS 260-279-1; benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate; MFCD00011948; (1H-1,2,3-benzotriazol-1-yloxy)(tri(dimethylamino))phosphonium hexafluorophosphate; 6-Maleimidocaproicacid-NHS(EMCS); BOP
Related CAS
56602-32-5 (free base)
Appearance
White crystalline powder
Purity
99 % (HPLC)
Melting Point
> 130 °C (dec.)
Storage
2-8 °C
Solubility
Soluble in Dichloromethane; Insoluble in Water; Sparingly soluble in Acetone; Slightly soluble in Acetonitrile, Methanol
InChI
InChI=1S/C12H22N6OP.F6P/c1-15(2)20(16(3)4,17(5)6)19-18-12-10-8-7-9-11(12)13-14-18;1-7(2,3,4,5)6/h7-10H,1-6H3;/q+1;-1
InChI Key
MGEVGECQZUIPSV-UHFFFAOYSA-N
Canonical SMILES
CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
1. Correction: Facile functionalization at the C4 position of pyrimidine nucleosides via amide group activation with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and biological evaluations of the products
Hari K Akula, Hariprasad Kokatla, Graciela Andrei, Robert Snoeck, Dominique Schols, Jan Balzarini, Lijia Yang, Mahesh K Lakshman Org Biomol Chem. 2017 Feb 1;15(5):1268. doi: 10.1039/c7ob90013a.
Correction for 'Facile functionalization at the C4 position of pyrimidine nucleosides via amide group activation with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and biological evaluations of the products' by Hari K. Akula, et al., Org. Biomol. Chem., 2017, DOI: 10.1039/c6ob02334g.
2. Facile Modifications at the C4 Position of Pyrimidine Nucleosides via In Situ Amide Activation with 1H-Benzotriazol-1-yloxy-tris(dimethyl-amino)phosphonium Hexafluorophosphate
Hari K Akula, Mahesh K Lakshman Curr Protoc Nucleic Acid Chem. 2019 Mar;76(1):e73. doi: 10.1002/cpnc.73. Epub 2019 Jan 28.
Two approaches for C4 modifications of silyl-protected thymidine, 2'-deoxyuridine, and 3'-azido-2',3'-dideoxythymidine (AZT) are described. In both, nucleoside amide activation with 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and DBU yields O4 -(benzotriazol-1-yl) derivatives. These in situ-formed intermediates are reacted with various nucleophiles, resulting in C4 modifications. In the two-step, one-pot approach, the O4 -(benzotriazol-1-yl) nucleoside intermediates are initially produced by reactions of the nucleosides with BOP and DBU in THF. This step is fast and typically complete within 30 min. Subsequently, the O4 -(benzotriazol-1-yl) derivatives are reacted with nucleophiles, such as aliphatic and aromatic amines, thiols, and alcohols, under appropriate conditions. Workup, isolation, and purification lead to the desired C4-modified pyrimidine nucleosides in good to excellent yields. In the one-step approach, the nucleosides are reacted with BOP and DBU, in the presence of the nucleophile (only aliphatic and aromatic amines, and thiols have been tested). Where comparisons are possible, the one-step approach is generally superior. © 2019 by John Wiley & Sons, Inc.
3. Facile functionalization at the C4 position of pyrimidine nucleosides via amide group activation with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and biological evaluations of the products
Hari K Akula, Hariprasad Kokatla, Graciela Andrei, Robert Snoeck, Dominique Schols, Jan Balzarini, Lijia Yang, Mahesh K Lakshman Org Biomol Chem. 2017 Feb 1;15(5):1130-1139. doi: 10.1039/c6ob02334g.
Reactions of O-t-butyldimethylsilyl-protected thymidine, 2'-deoxyuridine, and 3'-azidothymidine (AZT) with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) leads to activation of the C4 amide carbonyl by formation of putative O4-(benzotriazol-1-yl) derivatives. Subsequent substitution with alkyl and aryl amines, thiols, and alcohols leads to facile functionalization at this position. Reactions with amines and thiols were conducted either as a two-step, one-pot transformation, or as a one-step conversion. Reactions with alcohols were conducted as two-step, one-pot transformations. In the course of these investigations, the formation of 1-(4-pyrimidinyl)-1H-benzotriazole-3-oxide derivatives from the pyrimidine nucleosides was identified. However, these too underwent conversion to the desired products. Products obtained from AZT were converted to the 3'-amino derivatives by catalytic reduction. All products were assayed for their abilities to inhibit cancer cell proliferation and for antiviral activities. Many were seen to be active against HIV-1 and HIV-2, and one was active against herpes simplex virus-1 (HSV-1).
Online Inquiry
Verification code
Inquiry Basket