The synthesis of oseltamivir phosphate key intermediate, tert-butyl (5-(pentan-3-yloxy)-6- ((trimethylsilyl)oxy)cycloh ex-3-en-1-yl)carbamate and synthesis of (1S,2S)- hydroxycyclohexene-1,2,3- triazole derivatives / Sufi An-Nur Abd Haris

Oseltamivir phosphate also known as Tamiflu is an active neuraminidase inhibitor for the treatment of influenza A and B. In this study, a new method on synthesizing a key intermediate of oseltamivir phosphate was established by using commercially available 1,4-cyclohexadiene as the starting material...

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Main Author:	Abd Haris, Sufi An-Nur
Format:	Thesis
Language:	English
Published:	2022
Subjects:	Public health Hygiene Preventive Medicine Study and teaching
Online Access:	https://ir.uitm.edu.my/id/eprint/76731/1/76731.pdf
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id	my-uitm-ir.76731
record_format	uketd_dc
spelling	my-uitm-ir.767312023-04-18T02:19:52Z The synthesis of oseltamivir phosphate key intermediate, tert-butyl (5-(pentan-3-yloxy)-6- ((trimethylsilyl)oxy)cycloh ex-3-en-1-yl)carbamate and synthesis of (1S,2S)- hydroxycyclohexene-1,2,3- triazole derivatives / Sufi An-Nur Abd Haris 2022 Abd Haris, Sufi An-Nur Public health. Hygiene. Preventive Medicine Study and teaching Oseltamivir phosphate also known as Tamiflu is an active neuraminidase inhibitor for the treatment of influenza A and B. In this study, a new method on synthesizing a key intermediate of oseltamivir phosphate was established by using commercially available 1,4-cyclohexadiene as the starting materials. In the first part, tert-butyl (5-(pentan-3- yloxy)-6-((trimethylsilyl)oxy)cyclohex-3-en-1-yl)carbamate 14 (Tamiflu intermediate) was synthesized from 1,4-cyclohexadiene via epoxidation using m-CPBA to give cyclohexene epoxide 8, followed by epoxide ring opening with trimethyl silane azide using Salen catalyst complex to afford azide 9 and 10. Then the azide 9 was reduced by using Pd(OH)2/C and the resulted amine was protected with ditert-butyldicarbonate to give 11 and 12, followed by allylic oxidation of 11 with SeO2 and TBHP to afford 13. The compound 14, was synthesized via etherification reaction of dialcohol 11 with 3- pentanol catalyzed by BF3.OEt2 with the overall yield of 13%. The second part focused on the synthesis triazole derivatives 15a-15d using azide 10 as the starting material via click reaction employing iodocopper CuI[P(OEt)3] complex in toluene to afford triazole derivatives 15a-15d with the yield of 17- 29%. Both oseltamivir phosphate key intermediate and triazole derivatives explore new synthetic approaches towards the development of new chemicals for bioactivity purposes 2022 Thesis https://ir.uitm.edu.my/id/eprint/76731/ https://ir.uitm.edu.my/id/eprint/76731/1/76731.pdf text en public masters Universiti Teknologi MARA (UiTM) Faculty of Applied Sciences Mohd Ali, Mohd Tajudin
institution	Universiti Teknologi MARA
collection	UiTM Institutional Repository
language	English
advisor	Mohd Ali, Mohd Tajudin
topic	Public health Hygiene Preventive Medicine Study and teaching
spellingShingle	Public health Hygiene Preventive Medicine Study and teaching Abd Haris, Sufi An-Nur The synthesis of oseltamivir phosphate key intermediate, tert-butyl (5-(pentan-3-yloxy)-6- ((trimethylsilyl)oxy)cycloh ex-3-en-1-yl)carbamate and synthesis of (1S,2S)- hydroxycyclohexene-1,2,3- triazole derivatives / Sufi An-Nur Abd Haris
description	Oseltamivir phosphate also known as Tamiflu is an active neuraminidase inhibitor for the treatment of influenza A and B. In this study, a new method on synthesizing a key intermediate of oseltamivir phosphate was established by using commercially available 1,4-cyclohexadiene as the starting materials. In the first part, tert-butyl (5-(pentan-3- yloxy)-6-((trimethylsilyl)oxy)cyclohex-3-en-1-yl)carbamate 14 (Tamiflu intermediate) was synthesized from 1,4-cyclohexadiene via epoxidation using m-CPBA to give cyclohexene epoxide 8, followed by epoxide ring opening with trimethyl silane azide using Salen catalyst complex to afford azide 9 and 10. Then the azide 9 was reduced by using Pd(OH)2/C and the resulted amine was protected with ditert-butyldicarbonate to give 11 and 12, followed by allylic oxidation of 11 with SeO2 and TBHP to afford 13. The compound 14, was synthesized via etherification reaction of dialcohol 11 with 3- pentanol catalyzed by BF3.OEt2 with the overall yield of 13%. The second part focused on the synthesis triazole derivatives 15a-15d using azide 10 as the starting material via click reaction employing iodocopper CuI[P(OEt)3] complex in toluene to afford triazole derivatives 15a-15d with the yield of 17- 29%. Both oseltamivir phosphate key intermediate and triazole derivatives explore new synthetic approaches towards the development of new chemicals for bioactivity purposes
format	Thesis
qualification_level	Master's degree
author	Abd Haris, Sufi An-Nur
author_facet	Abd Haris, Sufi An-Nur
author_sort	Abd Haris, Sufi An-Nur
title	The synthesis of oseltamivir phosphate key intermediate, tert-butyl (5-(pentan-3-yloxy)-6- ((trimethylsilyl)oxy)cycloh ex-3-en-1-yl)carbamate and synthesis of (1S,2S)- hydroxycyclohexene-1,2,3- triazole derivatives / Sufi An-Nur Abd Haris
title_short	The synthesis of oseltamivir phosphate key intermediate, tert-butyl (5-(pentan-3-yloxy)-6- ((trimethylsilyl)oxy)cycloh ex-3-en-1-yl)carbamate and synthesis of (1S,2S)- hydroxycyclohexene-1,2,3- triazole derivatives / Sufi An-Nur Abd Haris
title_full	The synthesis of oseltamivir phosphate key intermediate, tert-butyl (5-(pentan-3-yloxy)-6- ((trimethylsilyl)oxy)cycloh ex-3-en-1-yl)carbamate and synthesis of (1S,2S)- hydroxycyclohexene-1,2,3- triazole derivatives / Sufi An-Nur Abd Haris
title_fullStr	The synthesis of oseltamivir phosphate key intermediate, tert-butyl (5-(pentan-3-yloxy)-6- ((trimethylsilyl)oxy)cycloh ex-3-en-1-yl)carbamate and synthesis of (1S,2S)- hydroxycyclohexene-1,2,3- triazole derivatives / Sufi An-Nur Abd Haris
title_full_unstemmed	The synthesis of oseltamivir phosphate key intermediate, tert-butyl (5-(pentan-3-yloxy)-6- ((trimethylsilyl)oxy)cycloh ex-3-en-1-yl)carbamate and synthesis of (1S,2S)- hydroxycyclohexene-1,2,3- triazole derivatives / Sufi An-Nur Abd Haris
title_sort	synthesis of oseltamivir phosphate key intermediate, tert-butyl (5-(pentan-3-yloxy)-6- ((trimethylsilyl)oxy)cycloh ex-3-en-1-yl)carbamate and synthesis of (1s,2s)- hydroxycyclohexene-1,2,3- triazole derivatives / sufi an-nur abd haris
granting_institution	Universiti Teknologi MARA (UiTM)
granting_department	Faculty of Applied Sciences
publishDate	2022
url	https://ir.uitm.edu.my/id/eprint/76731/1/76731.pdf
_version_	1783736120655216640

The synthesis of oseltamivir phosphate key intermediate, tert-butyl (5-(pentan-3-yloxy)-6- ((trimethylsilyl)oxy)cycloh ex-3-en-1-yl)carbamate and synthesis of (1S,2S)- hydroxycyclohexene-1,2,3- triazole derivatives / Sufi An-Nur Abd Haris

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