Two synthetic strategies have been developed for the synthesis of spaced sugars with lipophilic 1,4-phenylene core. A building block combining the usefulness of Weinreb amide functionality and modified Julia olefination reaction has been explored towards this objective. This building block offers complete flexibility in attaching any desired sugar derivative across phenylene spacer via C-C bond formation. The other strategy uses carbohydrate based building blocks for the synthesis of symmetrical as well as unsymmetrical 1,4-phenylene spaced sugars. This is the first report for the synthesis of 1,4-phenylene spaced sugars via C-C bond formation. © 2011 Elsevier Ltd. All rights reserved. 36.

Indrapal Singh Aidhen

Department Of Chemistry

Building blockes

C-C bond formation

JULIA OLEFINATION

PHENYLENE SPACERS

STRATEGY USE

sugar derivatives

Sulfones

Synthetic strategies

WEINREB AMIDES

Amides

Aromatic compounds

Synthesis (chemical)

Sugars

1,4 PHENYLENE

amide

carbohydrate

sugar

unclassified drug

article

chemical bond

chemical structure

Olefination

priority journal

synthesis

ACETYLATION

Carbohydrates

Chemistry Techniques, Synthetic

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Carbohydrate Research

Three new synthetic equivalents containing Weinreb amide functionality for the central core of FTY720, an immunosuppressive agent, have been developed. These synthetic equivalents enabled incorporation of the polar head group of FTY720, through Julia, Wittig, and Horner-Wadsworth-Emmons reactions and also allowed for variation in the chain length of the lipophilic side chain in target, through the Weinreb amide functionality therein. The use of tris(hydroxymethyl)aminomethane, commercially available at low cost for the polar head group offers a distinct advantage. Convenient reactions and simple functional group interconversions in good to high yield highlight the strength of the new route developed for the synthesis of clinically important FTY720. © Georg Thieme Verlag Stuttgart.

Synlett

Weinreb amide based new synthetic equivalents for convenient access to immunosuppressive agent FTY720 and analogues

The presence of an isopropylidene ketal protection of an internal diol in 3,4-O-isopropylidene-D-arabino-1-C-phenyl hexanone locks it in a conformation that prevents its cyclization to a pyranose ring. © 2003 Elsevier Ltd. All rights reserved.

Consequences of rigidity and conformational locking in a 4,4-dimethyl-1,3-dioxolane ring system during protection of internal diol

Tetrahedron

Total synthesis of diastereomeric marine butenolides possessing a syn-aldol subunit at C10 and C11 and the related C11-ketone

Journal	Carbohydrate Research
ISSN	00086215
Open Access	No