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Full and partial differentiation of tris-1,1,1-(hydroxymethyl)ethane via direct and indirect methodology

Full and partial differentiation of tris-1,1,1-(hydroxymethyl)ethane via direct and indirect methodology
Full and partial differentiation of tris-1,1,1-(hydroxymethyl)ethane via direct and indirect methodology
Tris-1,1,1-(hydroxymethyl)ethane 1 was converted to a series of mono- and disubstituted derivatives. An indirect protocol for the differentiation of the alcohol groups was employed for the synthesis of partially and fully differentiated 1 containing a protected aldehyde unit. Complete differentiation of the alcohol groups was also achieved using a direct strategy (two steps from 1). The first synthesis of 1,3-dialclehydes derived from 1 is reported in two steps.
scaffold, building block, alcohol differentiation, chemoselective acetal cleavageo-iodoxybenzoic acid, ring-closing metathesis, surfacefunctionalization, pentaerythritol, oxidation, alcohols, diols, derivatives, 1, 4-diols, reduction
0040-4020
3625-3636
Clarke, P.
9bf00ed7-b5fb-4b93-9eb7-46449b1ca69d
Jeffery, M. J.
93c5fbd6-ccac-4267-a452-89cf70fd2101
Boydell, A. J.
e06d686e-b65b-49c2-a45a-117e2d380ae3
Whiting, S.
6ac87eca-4789-478d-a7bc-1fcb950a0193
Linclau, B.
19b9cacd-b8e8-4c65-af36-6352cade84ba
Clarke, P.
9bf00ed7-b5fb-4b93-9eb7-46449b1ca69d
Jeffery, M. J.
93c5fbd6-ccac-4267-a452-89cf70fd2101
Boydell, A. J.
e06d686e-b65b-49c2-a45a-117e2d380ae3
Whiting, S.
6ac87eca-4789-478d-a7bc-1fcb950a0193
Linclau, B.
19b9cacd-b8e8-4c65-af36-6352cade84ba

Clarke, P., Jeffery, M. J., Boydell, A. J., Whiting, S. and Linclau, B. (2004) Full and partial differentiation of tris-1,1,1-(hydroxymethyl)ethane via direct and indirect methodology. Tetrahedron, 60 (16), 3625-3636. (doi:10.1016/j.tet.2004.02.056).

Record type: Article

Abstract

Tris-1,1,1-(hydroxymethyl)ethane 1 was converted to a series of mono- and disubstituted derivatives. An indirect protocol for the differentiation of the alcohol groups was employed for the synthesis of partially and fully differentiated 1 containing a protected aldehyde unit. Complete differentiation of the alcohol groups was also achieved using a direct strategy (two steps from 1). The first synthesis of 1,3-dialclehydes derived from 1 is reported in two steps.

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More information

Published date: 12 April 2004
Keywords: scaffold, building block, alcohol differentiation, chemoselective acetal cleavageo-iodoxybenzoic acid, ring-closing metathesis, surfacefunctionalization, pentaerythritol, oxidation, alcohols, diols, derivatives, 1, 4-diols, reduction

Identifiers

Local EPrints ID: 20168
URI: http://eprints.soton.ac.uk/id/eprint/20168
ISSN: 0040-4020
PURE UUID: b1c94a0f-64a3-4f9d-b970-9851a322bdba
ORCID for B. Linclau: ORCID iD orcid.org/0000-0001-8762-0170

Catalogue record

Date deposited: 17 Feb 2006
Last modified: 18 Feb 2021 16:55

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Contributors

Author: P. Clarke
Author: M. J. Jeffery
Author: A. J. Boydell
Author: S. Whiting
Author: B. Linclau ORCID iD

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