Journal ArticleDOI
Silyl migration and formation of an anhydro derivative on attempted benzylation of 3-O-tert-butyldimethylsilyl-6-O-tosyl-d-glucal
David Crich,Ritchie Timothy John +1 more
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TLDR
Synthese d'anhydro-3,6 O-t-butyldimethylsilyl-4 glucal a partir d'O-tosyl-6 glucal et de butyl chloro dimethyl silaneAbout:
This article is published in Carbohydrate Research.The article was published on 1990-03-25. It has received 14 citations till now. The article focuses on the topics: Glucal & Tosyl.read more
Citations
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Stereoselective synthesis of 2-deoxy-β-glycosides from glycal precursors. 1. Stereochemistry of the reactions of d-glucal derivatives with phenylsulfenyl chloride and phenylselenenyl chloride
TL;DR: The stereoselectivity of d-glucal derivatives with PhSCl and PhSeCl is dependent on the presence of an electronegative heteroatom substituent and the nature of the functionality at C(4) as discussed by the authors.
Journal ArticleDOI
Migration of secondary tert-butyldimethylsilyl groups in cyclomalto-heptaose and -octaose derivatives
Detlef Icheln,Bärbel Gehrcke,Yvonne Piprek,Petra Mischnick,Wilfried A. König,Marco A. Dessoy,Ademir F. Morel +6 more
TL;DR: The detection and identification of the reaction step during which migration of the secondary 2-O-tert-butyldimethylsilyl groups occurs is described and possible mechanisms of migration are discussed.
Journal ArticleDOI
A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction.
TL;DR: Homoallylation of aldehydes with isoprene and triethylborane catalyzed by Ni(acac)(2) gave hydroxyalkenes in good yield with excellent regio- and stereoselectivity and underwent cyclization in the presence of DBU to produce tetrahydrofurans.
Journal ArticleDOI
Sequential diastereoselective free radical reactions: Synthesis of an advanced olivomycin A C–D disaccharide
David Crich,Frank Hermann +1 more
TL;DR: In this article, the synthesis of an advanced olivomycin A C-D disaccharide is described in which the anomeric configuration of both 2-deoxy-β-glycosidic linkages is determined by a sequential diastereoselective radical reaction at the end of the synthesis.
References
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Journal ArticleDOI
The use of alkoxy-substituted anomeric radicals for the construction of β-glycosides
Journal ArticleDOI
Synthesis of 1-O-(1,2-di-O-palmitoyl-sn-glycero-3-phospho)-d-myo-inositol 4,5-bisphosphate: an analogue of naturally occurring (ptd)Ins(4,5)P2
TL;DR: Optically active 2,3,6-tri-O-benzyl-4,5-di-O-(trans-prop-1-enyl)-D-myo-inositol and 1,2-di,O-palmitoyl-sn-glycerol were coupled using mono- and bifunctional phosphitylating reagents to yield the chiral title compound.
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Studies of the selective silylation of methyl α- and β-d-aldohexopyranosides: stability of the partially protected derivatives in polar solvents
TL;DR: In this paper, a mixture of tert-butyldimethylsilyl (TBDMS) chloride under two conditions afforded mixtures of TBDMS ethers which were identified.
Journal ArticleDOI
Isomerization of tert-butyldimethylsilyl protecting groups in ribonucleosides
TL;DR: The tert-butyldimethylsilyl group undergoes isomerization between 0-2′ and 0-3′ in ribonucleosides in solution as mentioned in this paper.
Journal ArticleDOI
Direct 3,6-di-O-protection of glucal and galactal
Willy Kinzy,Richard R. Schmidt +1 more
TL;DR: In this article, Butyldimethylsilyl chloride is used for direct 3,6-di-O -protection of D-glucal and D-galactal.
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THE PREPARATION OF 4,6-O-BENZYLIDENE-D-GLUCAL AND THE REACTION OF METHYLLITHIUM WITH METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-α-D-ALLOPYRANOSIDE
M. Sharma,R. K. Brown +1 more