169105-89-9Relevant articles and documents
Synthesis of isofagomine and some new azasugars as glycosidase inhibitors from d-mannitol derived nitroolefins
Roy, Rashmi,Kancharla, Pavan K.,Reddy, Y. Suman,Brar, Anita,Vankar
, p. 1502 - 1513 (2013)
The synthesis of isofagomine, epi-isofagomine and isofagomine analogues along with some new azasugars from two different vinyl nitro compounds, that were derived from d-mannitol, has been carried out. Two different synthetic strategies were followed for e
Asymmetric synthesis of all stereoisomers of isofagomine using [2,3]-Wittig rearrangement
Mihara, Yukiko,Ojima, Hidetomo,Imahori, Tatsushi,Yoshimura, Yuichi,Ouchi, Hidekazu,Takahata, Hiroki
, p. 633 - 645 (2007)
The asymmetric synthesis of all stereoisomers of isofagomine from 5-hydroxymethyl-3-piperidene 6, which was prepared by [2,3 ]-Wittig rearrangement of O-alkylstannylmethyl compound 5 derived from readily available chiral 3-hydroxypiperidene 4, is describe
Synthesis of (+)-isofagomine
Kulkarni, Mukund G.,Shaikh, Yunnus B.,Birhade, Deekshaputra R.,Borhade, Ajit S.,Chavhan, Sanjay W.,Dhondge, Attrimuni P.,Gaikwad, Dnyaneshwar D.,Dhatrak, Nagorao R.
, p. 1234 - 1237 (2012/11/07)
The synthesis of (+)-isofagomine 1 using 4-pentenol 3 as a chiral precursor is described herein.
Acceleration effect of an allylic hydroxy group on ring-closing enyne metathesis of terminal alkynes: Scope, application, and mechanistic insights
Imahori, Tatsushi,Ojima, Hidetomo,Yoshimura, Yuichi,Takahata, Hiroki
experimental part, p. 10762 - 10771 (2009/12/01)
An interesting acceleration effect of an allylic hydroxy group on ring-closing enyne metathesis has been found. Ring-closing enyne metathesis of terminal alkynes possessing an allylic hydroxy group proceeded smoothly without the ethylene atmosphere generally necessary to promote the reaction. The synthesis of (+)-isofagomine with the aid of this efficient reaction has been demonstrated. Mechanistic studies of the acceleration effect were also carried out. Results of NMR studies suggested that the reaction proceeded via an "ene-then-yne" pathway. Kinetic studies indicated switching of the rate-determining step as a consequence of the presence of an allylic hydroxy group. These results suggest acceleration of the reentry step of Ru-carbene species by the allylic hydroxy group.