55722-48-0Relevant articles and documents
Efficient synthesis of thioglycosides via a Mitsunobu condensation
Falconer, Robert A.,Jablonkai, Istvan,Toth, Istvan
, p. 8663 - 8666 (1999)
Thioglycosides were synthesised from 1-thiosugars and a series of alcohols under Mitsunobu conditions using 1,1'-(azodicarbonyl)dipiperidine and trimethylphosphine. The conditions were found to be compatible with a wide range of functionalities and protec
A NEW, STEREOSELECTIVE SYNTHESIS OF METHYL 1,2-TRANS-1-THIOGLYCOSIDES
Pozsgay, Vince,Jennings, Harold J.
, p. 1375 - 1376 (1987)
Per-O-acetylated glycopyranoses were converted by methylthiotrimethylsilane in the presence of boron trifluoride or trimethylsilyl trifluoromethanesulfonate to the corresponding methyl 1,2-trans-1-thioglycopyranosides in a highly stereoselective process.
MANUFACTURE OF LACTO-N-TETRAOSE
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Page/Page column 54, (2012/12/13)
The present invention relates to the synthesis of the tetrasaccharide of formula (I) and novel intermediates used in the synthesis.
Indium(III) triflate: A highly efficient catalyst for reactions of sugars
Giri, Santosh Kumar,Verma, Monika,Kartha, K. P. Ravindranathan
scheme or table, p. 464 - 478 (2009/04/06)
Indium(III) trifluoromethanesulfonate has been found to be extremely efficient in catalyzing acyl transfer reactions of various carbohydrates and their derivatives. Selective acetolyses of certain benzyl ethers/isopropylidene acetals of sugars have been possible using In(OTf)3 in Ac2O (neat). Reaction of the per-O-acetate of 2-deoxy-2-phthalimido-D-glucose with benzyl mercaptan in the presence of In(OTf)3 led to the formation of the corresponding thioglycoside in high yield. Facile formation and hydrolysis of the isopropylidene and benzylidene acetals of various carbohydrates have also been achieved very efficiently in the presence of In(OTf)3. The results show great promise for In(OTf)3 in synthetic carbohydrate chemistry.
Modified one-pot protocol for the preparation of thioglycosides from unprotected aldoses via S-glycosyl isothiouronium salts
Tiwari, Pallavi,Agnihotri, Geetanjali,Misra, Anup Kumar
, p. 723 - 732 (2007/10/03)
An efficient one-pot protocol for the direct preparation of thioglycosides starting from unprotected reducing sugars via S-glycosyl isothiouronium salts is reported. In this one-pot methodology, BF3·OEt2 has been used as a general catalyst for both per-O-acetylation of sugars and conversion of sugar per-O-acetates into S-glycosyl isothiouronium salts, which was allowed to react with alkylating agents in the presence of a base to furnish thioglycosides in excellent yield. Copyright Taylor & Francis, Inc.
Streamlined synthesis of per-O-acetylated sugars, glycosyl iodides, or thioglycosides from unprotected reducing sugars
Mukhopadhyay, Balaram,Kartha, K.P. Ravindranathan,Russell, David A.,Field, Robert A.
, p. 7758 - 7760 (2007/10/03)
Solvent-free per-O-acetylation of sugars with stoichiometric acetic anhydride and catalytic iodine proceeds in high yield (90-99%) to give exclusively pyranose products as anomeric mixtures. Without workup, subsequent anomeric substitution employing iodine in the presence of hexamethyldisilane (i.e., TMS-I generated in situ) gives the corresponding glycosyl iodides in 75-95% isolated yield. Alternatively, and without workup, further treatment with dimethyl disulfide or thiol (ethanethiol or thiocresol) gives anomerically pure thioglycosides in more than 75% overall yield.
Iodine and its interhalogen compounds: Versatile reagents in carbohydrate chemistry v. synthesis of 1,2-trans-linked 1-thioglycosides from the per-o-acetylated glycoses
Kartha, K. P. Ravindranathan,Field, Robert A.
, p. 693 - 702 (2007/10/03)
Treatment of per-O-acetylated mono- and di-saccharides with (alkyl/arylthio)trimethylsilane and iodine at ambient temperature results in the formation of the corresponding 1,2-trans-1-thioglycosides in very high yield. In the case of higher boiling thiols such as ethanethiol, the reaction can be effectively carried out in the presence of the thiol itself instead of the silylated derivative, but the reaction is not stereospecific. Moreover, in the latter reactions a portion of the starting material remains unchanged even on prolonged reaction. With β-D-glucose pentaacetate (11) as the starting material, its epimerisation occurred during the reaction and therefore the recovered starting material was of α-D-configuration. In addition, the methyl disulphide-hexamethyldisilane system has been found to serve as an effective and cheaper alternative to the expensive (methylthio)-trimethylsilane.
Reaction of sugar thiocyanates with Grignard reagents. New synthesis of thioglycosides
Pakulski, Zbigniew,Pierozynski, Donat,Zamojski, Aleksander
, p. 2975 - 2992 (2007/10/02)
Glycosyl thiocyanates having hydroxyl groups protected with acetyl or benzoyl groups react readily at -40°C with Grignard reagents to afford the corresponding alkyl or aryl thioglycosides in good yields. Monosaccharide derivatives having the SCN grouping at other positions form under similar conditions thioethers. Axial thiocyanates do not react. Elevated temperatures induce side reactions leading to mercaptans.
SYNTHESIS OF A SULFATED GLYCOPEPTIDE CORRESPONDING TO THE CARBOHYDRATE-PROTEIN LINKAGE REGION OF PROTEOGLYCANS: β-D-GlcA-(1->3)4)>-β-D-Gal-(1->3)-β-D-Gal-(1->4)-β-D-Xyl-(1->3)-Ser
Goto, Fumitaka,Ogawa, Tomoya
, p. 5099 - 5102 (2007/10/02)
A sulfated glycotetraosyl serin 4 was synthesized in a stereocontrolled manner by employing a key glycotetraosyl donor 7 and a serine derivative 6.
Synthesis of Oligosaccharides Corresponding to the Common Polysaccharide Antigen of Group B Streptococci
Pozsgay, Vince,Jennings, Harold J.
, p. 4042 - 4052 (2007/10/02)
To facilitate mapping of the immunodominant region of the common polysaccharide antigen of group B streptococci, tetrasaccharide 1-O--α-rhamnopyranosyl>-D-glucitol (2) was synthesized in a stepwise fasion
