BOP (Coupling Reagent), Castro's reagent [56602-33-6] HEADING_TITLE

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

Other Name: (Benzotriazolyloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Castro's Reagent

Catalog #: CXZ001 CAS #: 56602-33-6
Formula: C12H22F6N6OP2 M.W.: 442.3

BOP

 

 

 

 

 

 

BOP suppresses racemization during activation and coupling. It was first descibed by Castro in 1975 (B Castro, et al., Tetrahedron Lett., 1975, 1219-22).  It has largely been replaced by other coupling reagents in solid phase peptide synthesis because the byproduct hexamethylphosphotriamide (HMPA) is a carcinogen.  However, BOP is still used in various applications, especially in solution phase chemistry.  It was recently utilized to conjugate Flt1 peptide to hyaluronic acid.  The resulting conjugate self-assembled into nanoparticles which were loaded with dexamethasone to overcome corticosteroid resistance for the treatment of neutrophilic pulminary inflammation (H. Kim, et al., Biomaterials, 2013, 34, 8478-98).  

BOP has been used in the facile and chemoselective reduction of carboxyklic acids to alcohols.  BOP is reacted with the carboxylic acid to form the hydroxybenzotriazolyl ester, which in turn is reduced to the alcohol with sodium borohydride in THF (Z-F Tao, I Saito, H. Sugiyama, J. Am. Chem. Soc., 2000, 122, 1602-8; B Nottelet, et al., Biomacromolecules, 2012, 13, 1544-53).

BOP Physical Properties

Assay:  97+%

White to tan powder

Mp:  138 °C (dec)(lit)

Storage temp: 2-8 °C

Solubility: 0.6 mmol in 1 mL DMF

BOP Reagent References

PJ Marsouvanidis, et al., J. Med. Chem., 2013, 56,2374-84.

AJ Brouwer, et al., J. Med. Chem., 2012, 55, 10995-1003.

KE Wells, et al., Crystal Growth & Design, 2012, 12, 5056-68.

DS Nielson, et al., Org. Lett., 2012, 14, 5720-3.

L Widanapathirana, Y Zhao, J. Org. Chem., 2012, 77, 4679-87.

A Duranti, et al., J. Med. Chem., 2012, 55, 4824-36.

A Papadopoulos, TC Shiao, R Roy, Mol. Pharmaceutics, 2012, 9, 394-403.

Other Products Related to BOP Reagent

Cat. # Product Cat. # Product
CXZ090 BOP-Cl CXZ002 CDI
CXZ031 COMU CXZ003 DCC
CXZ004 DIC CXZ060 DEPBT
CXZ009 DSC CXZ005 EDC
CXZ025 HATU CXZ020 HBTU
CXZ030 HCTU CXZ012 HOAt
CXZ010 HOBt H2O CXZ096 6-Cl-HOBt
CXZ015 HOOBt CXZ022 HOSu
CXZ021 Oxyma CXZ070 PyAOP
CXZ050 PyBOP CXZ055 PyBrOP
CXZ045 TATU CXZ040 TBTU
CXZ042 TCFH CXZ065 TDBTU
CXZ043 TNTU CXZ044 TOTU
CXZ046 TPTU CXZ041 TSTU




 


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