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Synthesis of carbasugar derivatives via a "Pseudo"-C2-symmetric building block derived from arabitol

Synthesis of carbasugar derivatives via a "Pseudo"-C2-symmetric building block derived from arabitol
Synthesis of carbasugar derivatives via a "Pseudo"-C2-symmetric building block derived from arabitol

Development of a kinetic protection protocol for arabitol affords the "pseudo"-C2- symmetric bis-acetal 8 in good yield. Utilising a scavenging purification strategy greatly simplifies the separation of 8 from the thermodynamically more stable regioisomeric byproduct 7. The building block 8 is utilised in a series of syntheses to yield a "pseudo"-C2- symmetric and C2-symmetric 1,4-bis-epoxides in 3 and 5 steps, respectively, from 8. These bis-epoxides are then reacted with a dithiane stabilised carbanion in a Brook rearrangement mediated cyclisation to furnish carbasugar derivatives in enantiopure form. The "pseudo"-C2-symmetric bis-epoxide gives a distereomeric mixture as expected, while the CVsymmetric bis-epoxide reacts to form only one diastereomer.

University of Southampton
Boydell, Alan James
Boydell, Alan James

Boydell, Alan James (2003) Synthesis of carbasugar derivatives via a "Pseudo"-C2-symmetric building block derived from arabitol. University of Southampton, Doctoral Thesis.

Record type: Thesis (Doctoral)

Abstract

Development of a kinetic protection protocol for arabitol affords the "pseudo"-C2- symmetric bis-acetal 8 in good yield. Utilising a scavenging purification strategy greatly simplifies the separation of 8 from the thermodynamically more stable regioisomeric byproduct 7. The building block 8 is utilised in a series of syntheses to yield a "pseudo"-C2- symmetric and C2-symmetric 1,4-bis-epoxides in 3 and 5 steps, respectively, from 8. These bis-epoxides are then reacted with a dithiane stabilised carbanion in a Brook rearrangement mediated cyclisation to furnish carbasugar derivatives in enantiopure form. The "pseudo"-C2-symmetric bis-epoxide gives a distereomeric mixture as expected, while the CVsymmetric bis-epoxide reacts to form only one diastereomer.

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Published date: 2003

Identifiers

Local EPrints ID: 465065
URI: http://eprints.soton.ac.uk/id/eprint/465065
PURE UUID: bc8579d1-d68a-4576-8f33-582fef2faf65

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Date deposited: 05 Jul 2022 00:21
Last modified: 05 Jul 2022 04:06

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Author: Alan James Boydell

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