- Synthesis and Glycosylation Properties of C6-Silylated Ido- and Gluco-Pyranosyl Donors
-
Silyl groups are widely used as alcohol protecting groups and their study has provided insight on some very remarkable structure and reactivity features within carbohydrate chemistry. However, not much work has been put into the effect on the reactivity of silyl groups directly attached to the sugar carbon chain. In this work, we have developed a synthetic methodology to obtain both d-glucosyl and l-idosyl donors containing a dimethylphenylsilyl group directly attached to C6. Glycosylation and competition experiments with different glycosyl acceptors have shown that this group is completely stable under glycosylation conditions and enhances reactivity beyond what a benzyl group attached to the sugar oxygen would do. Finally, we found adequate conditions for the protodesilylation of Si-containing glycosides to yield the 6-deoxy sugar analog.
- álvarez-Martínez, Ignacio,Pedersen, Christian Marcus
-
-
- METHOD FOR PREPARING 3-O-BENZYL-1,2-O-ISOPROPYLIDENE-A-L-FURAN IDOSE
-
Provided is a method for preparing 3-O-benzyl-1,2-O-isopropylidene-α-L-idofuranose, which comprises: (1) protecting hydroxyl of 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (III) by benzoyl and methylsulfonyl to obtain 6-O-benzoyl-3-O-benzyl-1,2-O-is
- -
-
-
- METHOD FOR PREPARING 3-O-BENZYL-1,2-O-ISOPROPYLIDENE- -L-FURAN IDOSE
-
Provided is a method for preparing 3-O-benzyl-1,2-O-isopropylidene-α-L-idofuranose, which comprises: (1) protecting hydroxyl of 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (III) by benzoyl and methylsulfonyl to obtain 6-O-benzoyl-3-O-benzyl-1,2-O-is
- -
-
-
- Design and synthesis of carbohydrate based medium sized sulfur containing benzannulated macrocycles: Applications of Sonogashira and Heck coupling
-
Palladium catalyzed intramolecular Sonogashira and Heck coupling reactions have been applied for diversity-oriented synthesis of sulfur containing carbohydrate based medium sized ring macrocycles. The process involves design and synthesis of building bloc
- Hussain, Altaf,Yousuf, Syed Khalid,Sharma, Deepak K.,Mallikharjuna Rao,Singh, Baldev,Mukherjee, Debaraj
-
p. 5517 - 5524
(2013/07/05)
-
- Synthesis of heparin oligosaccharides and their interaction with eosinophil-derived neurotoxin
-
A convenient route for the synthesis of heparin oligosaccharides involving regioselective protection of d-glucosamine and a concise preparation of rare l-ido sugars from diacetone α-d-glucose is described. Stereoselective coupling of a d-glucosamine-derived trichloroacetimidate with a 1,6-anhydro-β-l-idopyranosyl 4-alcohol gave the desired α-linked disaccharide, which was used as repeating unit for dual chain elongation and termination. Stepwise assembly from the reducing to the non-reducing end with a d-glucosamine-derived monosaccharide as starting unit furnished the oligosaccharide skeletons having different chain lengths. A series of functional group transformations afforded the expected heparin oligosaccharides with 3, 5 and 7 sugar units. Interaction of these oligosaccharides with eosinophil-derived neurotoxin (EDN), a cationic ribonuclease and a mediator produced by human eosinophils, was further investigated. The results revealed that at 5 μg mL-1, the heptasaccharide has sufficiently strong interference to block EDN binding to Beas-2B cells. The tri- and pentasaccharides have moderate inhibitory properties at 50 μg mL-1 concentration, but no inhibition has been observed at 10 μg mL-1. The IC50 values of the tri-, penta- and heptasaccharides are 69.4, 47.2 and 0.225 μg mL-1, respectively.
- Hung, Shang-Cheng,Lu, Xin-An,Lee, Jinq-Chyi,Chang, Margaret Dah-Tsyr,Fang, Shun-Lung,Fan, Tan-Chi,Zulueta, Medel Manuel L.,Zhong, Yong-Qing
-
p. 760 - 772
(2012/02/05)
-
- Total synthesis of L-(+)-swainsonine and other indolizidine azasugars from D-glucose
-
A total synthesis of L-(+)-swainsonine, a potent and specific inhibitor of naringinase, along with the syntheses of six unnatural indolizidine azasugars are reported by starting from D-glucose. L-(+)-Swainsonine was synthesized in 14 steps in 17% overall yield. Further, two of the indolizidine analogues were found to be good glycosidase inhibitors at micromolar concentrations. In all of these syntheses, the key step was an intramolecular SN2 reaction. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Alam, Mohammad Abrar,Kumar, Amit,Vankar, Yashwant D.
-
supporting information; experimental part
p. 4972 - 4980
(2009/05/27)
-
- Synthesis of a polysulfated heparin degradation product
-
Two suitable methods for the synthesis of the heparin degradation product 2,5-anyhydro-3-O-(α-L-ido-pyranosyluronate)-D-mannitol hexa O-sulfate are reported. The synthesis pathways start from D-glucose and D-glucosamine.
- Kuszmann, Janusz,Medgyes,Boros
-
p. 344 - 348
(2007/10/03)
-
- Concise and practical synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6-iminosugars
-
The syntheses of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6 iminosugars 1a and 1b, respectively, from D-glucose are described. The key transformations in this reaction sequence include regio-selective epoxide ring opening with N-benzylamine followed
- Tilekar, Jayant N.,Patil, Nitin T.,Jadhav, Harishchandra S.,Dhavale, Dilip D.
-
p. 1873 - 1876
(2007/10/03)
-
- Synthesis of nojirimycin derivatives
-
Nojirimycin δ-lactam and deoxynojirimycin are each synthesized from 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-L-idofuranose as a divergent intermediate by a method which comprises formation of the piperidine ring by connection of nitrogen between C-1 and C-5 with inversion of configuration at C-5 to form nojirimycin δ-lactam or between C-2 and C-6 with inversion of configuration at C-2.
- -
-
-
- Synthesis of nojirimycin derivatives
-
Nojirimycin δ-lactam and deoxynojirimycin are each synthesized from 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-L-idofuranose as a divergent intermediate by a method which comprises formation of the piperidine ring by connection of nitrogen between C-1 and C-5 with inversion of configuration at C-5 to form nojirimycin δ-lactam or between C-2 and C-6 with inversion of configuration at C-2.
- -
-
-
- SYNTHESIS OF SOME L-IDOSE DERIVATIVES
-
The synthesis of 3-O-benzyl and 3-O-mesyl-1,2-O-isopropylidene-β-L-idofuranose has been effected on the basis of the intramolecular nucleophilic exchange of a mesyloxy group at C5 in derivatives of 1,2-O-isopropylidene-α-D-glucofuranose.It has
- Grishkovets, V. I.,Zemlyakov, A. E.,Chirva, V. Ya.
-
p. 388 - 392
(2007/10/02)
-