TY - JOUR
T1 - O-Benzoxazolyl Imidates as Versatile Glycosyl Donors for Chemical Glycosylation
AU - Nigudkar, Swati S.
AU - Parameswar, Archana R.
AU - Pornsuriyasak, Papapida
AU - Stine, Keith J.
AU - Demchenko, Alexei V.
N1 - Herein, we report a new class of glycosyl donors, benzoxazolyl imidates, for chemical glycosylation. The O-benzoxazolyl (OBox) leaving group was designed with an aim to compare the relative reactivity and stability of similarly structured S-benzoxazolyl (SBox) glycosides (thioimidates) developed in our lab a
PY - 2013/1/1
Y1 - 2013/1/1
N2 - Herein, we report a new class of glycosyl donors, benzoxazolyl imidates, for chemical glycosylation. The O-benzoxazolyl (OBox) leaving group was designed with an aim to compare the relative reactivity and stability of similarly structured S-benzoxazolyl (SBox) glycosides (thioimidates) developed in our lab and glycosyl trichloroacetimidates (TCAI, O-imidates) developed by Schmidt. Novel OBox donors can be activated under catalytic conditions and provided excellent yields in glycosylation. The OBox imidates were found to be more reactive than either SBox or TCAI donors. The high reactivity profile was confirmed in direct competitive experiments and was found beneficial for HPLC-assisted solid-phase synthesis.
AB - Herein, we report a new class of glycosyl donors, benzoxazolyl imidates, for chemical glycosylation. The O-benzoxazolyl (OBox) leaving group was designed with an aim to compare the relative reactivity and stability of similarly structured S-benzoxazolyl (SBox) glycosides (thioimidates) developed in our lab and glycosyl trichloroacetimidates (TCAI, O-imidates) developed by Schmidt. Novel OBox donors can be activated under catalytic conditions and provided excellent yields in glycosylation. The OBox imidates were found to be more reactive than either SBox or TCAI donors. The high reactivity profile was confirmed in direct competitive experiments and was found beneficial for HPLC-assisted solid-phase synthesis.
UR - https://pubs.rsc.org/en/content/articlelanding/2013/ob/c3ob40667a?_escaped_fragment_=divAbstract#!
UR - http://pubs.rsc.org/en/content/articlelanding/2013/ob/c3ob40667a#!
U2 - 10.1039/C3OB40667A
DO - 10.1039/C3OB40667A
M3 - Article
VL - 11
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
ER -