63479-64-1Relevant academic research and scientific papers
Stereoselective synthesis of α-glucosides from 3-O-propargyl protected glucal exploiting the alkynophilicity of AuCl3
Kashyap, Sudhir,Hotha, Srinivas
, p. 2021 - 2023 (2006)
The stereoselective synthesis of 2,3-unsaturated α-d-glucosides by the SN2′ addition of diverse aglycones onto 4,6-di-O-benzyl-3-O-propargyl glucal was achieved using a catalytic quantity of AuCl3. The Au catalyzed reaction was explo
FeCl3/C as an efficient catalyst for Ferrier rearrangement of 3,4,6-tri-O-Benzyl-D-glucal
Mei, Yuling,Dong, Youxian,Li, Juan,Zhang, Bo,Sun, Guosheng,Zhou, Jiafen,Si, Wenshuai,Han, Yiwen,Wu, Zhenliang,Zhang, Jianbo
, p. 1 - 18 (2020/07/21)
FeCl3/C was used as an efficient and convenient promoter for glycosylation through Ferrier-type rearrangement of 3,4,6-tri-O-benzyl-D-glucal, which is a relatively unreactive substrate for this type of reaction. The method was applicable to a w
Gd(OTf)3 catalyzed preparation of 2,3-unsaturated O-, S-, N-, and C-pyranosides from glycals by Ferrier Rearrangement
Chen, Peiran,Su, Jie
supporting information, p. 84 - 94 (2015/12/23)
By using Gd(OTf)3 as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed by Ferrier Rearrangement. A series of 2,3-unsaturated O-, S-, N-, and C-glycosides were obtained from 3,4,6-tri-O-acetyl-d-glucal, 3,4,6-tri-O-benzyl-d-glucal, and 3,4-di-O-acetyl-l-rhamnal under mild reaction conditions in good yields and high anomeric selectivities.
Glycosylations of Glycals using N-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo- and 2-Deoxyglycosides
Kimura, Tomoya,Takahashi, Daisuke,Toshima, Kazunobu
, p. 9552 - 9562 (2015/10/12)
The glycosylations of glycals and alcohols using N-iodosuccinimide (NIS) and a catalytic amount of PPh3 effectively proceeded under mild conditions to provide the corresponding 2-deoxy-2-iodoglycosides in high yields. The reactivity of the iodo
Y(OTf)3 as a highly efficient catalyst in Ferrier Rearrangement for the synthesis of O- and S-2,3-unsaturated glycopyranosides
Chen, Peiran,Li, Shan
supporting information, p. 5813 - 5816 (2015/02/19)
By using Y(OTf)3 as the catalyst, a series of 2,3-unsaturated-glucosides have been synthesized from 3,4,6-tri-O-acetyl-d-glucal, 3,4-di-O-acetyl-l-rhamnal, and 3,4,6-tri-O-benzyl-d-glucal under mild reaction conditions in good yields with high anomeric selectivities. It was found that, in this reaction, 3,4,6-tri-O-benzyl-d-glucal behaved differently from the other two glucals when it was reacted with phenol, O-benzyl glucoside instead of O-phenyl glucoside formed as the sole product. An explanation is given for this phenomenon.
Aluminium triflate catalysed O-glycosidation: Temperature-switched selective Ferrier rearrangement or direct addition with alcohols
Williams, D. Bradley G.,Simelane, Sandile B.,Kinfe, Henok H.
supporting information; experimental part, p. 5636 - 5642 (2012/08/07)
A temperature-controlled mechanism switch between the Al(OTf) 3-catalysed direct addition of alcohols or the Ferrier rearrangement reactions in some glycals is presented. The scope and limitations are investigated as are the influence of the st
Palladium-catalyzed improved regio- and stereoselective O-glycosylation of D-glucal-derived β- And α-vinyl oxiranes
Reddy, Y. Suman,Lahiri, Rima,Vankar, Yashwant D.
, p. 4751 - 4761 (2012/10/08)
A Pd0-catalyzed glycosylation of D-glucal-derived vinyloxiranes as excellent glycosyl donors has been accomplished in a regio- and stereoselective manner. Various glycosyl acceptors upon reaction with vinyl oxiranes 1a and 1b produced the corre
Montmorillonite K-10 clay-catalyzed Ferrier rearrangement of 2-C-hydroxymethyl-D-glycals, 3,4,6-tri-O-alkyl-D-glycals, and 3,4-(dihydro-2H-pyran-5-yl)methanol: A few unexpected domino transformations
Kumaran, Elumalai,Santhi, Meenakshisundaram,Balasubramanian, Kalpattu K.,Bhagavathy, Shanmugasundaram
experimental part, p. 1654 - 1661 (2011/11/06)
Montmorillonite K-10 clay-catalyzed substitution reactions of 3,4,6-tri-O-alkyl-2-C-hydroxymethyl-Dglycals, 3,4,6-tri-O-acetyl-D-glycals, 3,4,6-tri-O-alkyl-D-glycals, and 3,4-(dihydro-2H-pyran-5-yl)methanol with a few alcohols and phenols are described. The reactions of 2-C-hydroxymethyl-D-glycals with phenols were similar to those of 2-C-acetoxymethyl-D-glycals and afforded pyrano[2,3-b]benzopyrans. This montmorillonite K-10 clay-catalyzed transformation is facile both under ambient (Method 1) and microwave conditions (Method 2). Ferrier rearrangement of 3,4-(dihydro-2H-pyran-5-yl)methanol with p-cresol, 2,6-xylenol, and ethanol led to totally unexpected transformations. Reaction of 2-C-hydroxymethyl- D-galactal with 2,6-dimethylphenol in the presence of montmorillonite K-10 led to a novel domino transformation affording 4-(5',6'-dihydro-4H-pyran-3'-ylmethyl)-2,6-dimethylphenol. In contrast, 3,4,6-tri-O-acetyl-D-glucal furnished the Ferrier rearrangement product, 2,6-dimethylphenyl 4,6-di-Oacetyl- 2,3-dideoxy-α-D-erythro-hex-2- enopyranoside. Also, isomerization of 3,4,6-tri-O-alkyl-D-glycals to products of allylic rearrangement, 2,3-unsaturated-O-glycosides in good yields is reported.
"Design" of boron-based compounds as pro-nucleophiles and co-catalysts for indium(I)-catalyzed allyl transfer to various Csp 3-type electrophiles
Dao, Hai Thanh,Schneider, Uwe,Kobayashi, Shu
experimental part, p. 2522 - 2529 (2012/07/13)
We have recently uncovered a general indium(I)-catalyzed method for allylations and propargylation of acetals and ketals with a water- and air-stable allyl boronate. By using a more reactive allyl borane, we have successfully extended this methodology to the more challenging C-C coupling with ethers. Herein, we report an improved methodology for the indium(I)-catalyzed allylation of acetals and ethers, through combination of the allyl boronate with a commercially available "hard" Lewis acid, B-methoxy-9-BBN (BBN=borabicyclo[3.3.1]nonane), as an effective co-catalyst. Significantly, our work highlights for the first time the correlation between the Lewis acidity of "electrophilic" boron-based compounds and their " nucleophilic" reactivity in Csp3-Csp3 couplings, catalyzed by a "soft" low-oxidation main group metal. In addition, we also report several applications of these methodologies to the selective synthesis of various carbohydrate derivatives. Copyright
2,3-unsaturated allyl glycosides as glycosyl donors for selective α-glycosylation
Kumar, Brijesh,Aga, Mushtaq A.,Rouf, Abdul,Shah, Bhahwal A.,Taneja, Subhash C.
supporting information; experimental part, p. 3506 - 3510 (2011/06/26)
In the presence of NBS and a catalytic amount of a Lewis acid, 2,3-unsaturated allyl glycosides [6-(allyloxy)-3,6-dihydro-2-(hydroxymethyl)-2H- pyran-3-ol] have been successfully used as versatile glycosyl donors for the stereoselective α-glycosylation of
