Stereocontrolled Synthesis of 1,2- and 1,3-Diamine Building Blocks from Aziridine Aldehyde Dimers

2013 ◽  
Vol 78 (23) ◽  
pp. 11637-11645 ◽  
Author(s):  
Sean K. Liew ◽  
Zhi He ◽  
Jeffrey D. St. Denis ◽  
Andrei K. Yudin
Keyword(s):  
Building Blocks ◽  
Stereocontrolled Synthesis ◽  
Aziridine Aldehyde

ChemInform Abstract: Stereocontrolled Synthesis of 1,2- and 1,3-Diamine Building Blocks from Aziridine Aldehyde Dimers.

ChemInform ◽  
2014 ◽  
Vol 45 (21) ◽  
pp. no-no
Author(s):  
Sean K. Liew ◽  
Zhi He ◽  
Jeffrey D. St. Denis ◽  
Andrei K. Yudin
Keyword(s):  
Building Blocks ◽  
Stereocontrolled Synthesis ◽  
Aziridine Aldehyde

scholarly journals Stereocontrolled Synthesis of Cyclopropanol Amino Acids from Allylic Sulfones: Conformationally Restricted Building Blocks.

ChemInform ◽  
2004 ◽  
Vol 35 (5) ◽  
Author(s):  
David Diez ◽  
P. Garcia ◽  
Isidro S. Marcos ◽  
N. M. Garrido ◽  
P. Basabe ◽  
...  
Keyword(s):  
Amino Acids ◽  
Building Blocks ◽  
Conformationally Restricted ◽  
Stereocontrolled Synthesis

Building Blocks for the Stereocontrolled Synthesis of 1,3-Diols of Various Configurations

Synlett ◽  
1997 ◽  
Vol 1997 (2) ◽  
pp. 225-228 ◽  
Author(s):  
Stefan Weigand ◽  
Reinhard Brückner
Keyword(s):  
Building Blocks ◽  
Stereocontrolled Synthesis

Stereocontrolled Synthesis of Cyclopropanol Amino Acids from Allylic Sulfones:  Conformationally Restricted Building Blocks

2003 ◽  
Vol 5 (20) ◽  
pp. 3687-3690 ◽  
Author(s):  
David Díez ◽  
P. Garcia ◽  
Isidro S. Marcos ◽  
N. M. Garrido ◽  
P. Basabe ◽  
...  
Keyword(s):  
Amino Acids ◽  
Building Blocks ◽  
Conformationally Restricted ◽  
Stereocontrolled Synthesis

Diastereomers of Nucleoside 3'-O-(2-Thio-1,3,2-oxathia(selena)phospholanes): Building Blocks for Stereocontrolled Synthesis of Oligo(nucleoside phosphorothioate)s

1995 ◽  
Vol 117 (49) ◽  
pp. 12019-12029 ◽  
Author(s):  
Wojciech J. Stec ◽  
Andrzej Grajkowski ◽  
Anna Kobylanska ◽  
Boleslaw Karwowski ◽  
Maria Koziolkiewicz ◽  
...  
Keyword(s):  
Building Blocks ◽  
Stereocontrolled Synthesis

scholarly journals Preparation of a set of selectively protected disaccharides for modular synthesis of heparan sulfate fragments: toward the synthesis of several O-sulfonated [β-D-GlcUA-(1→4)-β-D-GlcNAc]OPr types

2005 ◽  
Vol 3 (4) ◽  
pp. 803-829 ◽  
Author(s):  
Hammed Hassan
Keyword(s):  
Heparan Sulfate ◽  
Building Blocks ◽  
Protecting Groups ◽  
Hydroxyl Group ◽  
Hydroxyl Groups ◽  
Allyl Ethers ◽  
Modular Synthesis ◽  
Stereocontrolled Synthesis ◽  
Benzyl Ethers ◽  
Free Hydroxyl

AbstractA concise method for a stereocontrolled synthesis of a set of selectively protected disaccharides is reported. Coupling of the donor 11 onto acceptors 23 and 24, promoted by trimethylsilyl triflate-N-iodosuccinimide (TMSOTf-NIS), generated the disaccharides 25 and 26. Under typical conditions, condensation of the fully protected donor 12 onto acceptors 23 and 24 produced the disaccharides 27 and 28. The building blocks 25–28 were prepared in moderate yields having exclusive β-stereoselectivity. A unique pattern of protecting groups distinguished clearly between positions to be sulfated and functional groups remaining as free hydroxyl groups. Acetyl and/or levulinoyl esters temporarily protected the positions to be sulfated, while benzyl ethers were used for permanent protection. The anomeric positions were protected as allyl ethers, whereas the 4′-positions were masked as p-methoxybenzyl (PMB) ethers. The orthogonality of the PMB and allyl groups can then be used for further elongation of the chain by recurrent deprotection and activation steps. The hydroxyl group, OH-6, of glucosamine moieties was protected as a TBDPS ether to avoid oxidation. A five-step deprotection/sulfonation sequence was applied to the disaccharide 27 to generate the corresponding sulfated [β-D-GlcUA-2-OSO3Na-(1→4)-β-D-Glc pNAc]-(1→O-Pro) 34.

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