Lithiation study on D4T.

H Kumamoto; H Tanaka

doi:10.1093/nass/44.1.107

Home/Archive/PubMed

PubMed · 12903291

Lithiation study on D4T.

H Kumamoto·H Tanaka

View original source ↗Export metadata ↓

Abstract

Upon treatment with LTMP, 5'-O-protected D4T undergoes deprotonation of the vinylic proton (H-3' or H-2'): when 5'-O-silyl derivative was used, the 3'-C-silylated product was formed as a result of C3'-lithiation and subsequent O-->C silyl migration, while deprotonation at the 2'-position led to the formation of an allene derivative. A stannyl version of this reaction was also examined to develop a method for C3'-functionalization of D4T.

Explore related subjects

Lithium Methods Molecular Structure Stavudine Journal Article

Keep this discovery

Explore connections, maps & timelines

BibTeX RIS

H Kumamoto, H Tanaka. 2000. Lithiation study on D4T.. https://doi.org/10.1093/nass%2F44.1.107

Cite the original work for its findings. Save a collection to share your selection of sources.

KEEP EXPLORING

Related citations

PubMed2007

Origin of chemoselectivity of TMP zincate bases and differences between TMP zincate and alkyl lithium reagents: a DFT study on model systems.

Explore the source record for details and available documents.

Lithium↗

PubMed2006

Unusual sterically controlled regioselective lithiation of 3-bromo-5-(4,4'-dimethyl)oxazolinylpyridine. Straightforward access to highly substituted nicotinic acid derivatives.

[Structure: see text] Lithiation of 5-bromonicotinic acid protected as secondary or tertiary amide as well as (4,4'-dimethyl)oxazoline with lithium amides is reported. The unusual C-2 and C-4 regioselective lithiation of 3-bromo-5-(4,4'-dimethyl)oxazolinylpyridine using LTMP versus LDA was observed, providing a new route to substituted nicotinic acid scaffolds. The methodology was applied to the synthesis of novel C-4 and C-6 arylated 5-bromonicotinic acids.

Lithium↗

PubMed2005

A convenient oxazole C-2 protecting group: the synthesis of 4- and 5-substituted oxazoles via metalation of 2-triisopropylsilyloxazoles.

[reaction: see text] Metalation of oxazoles at the 4 and 5 position was achieved after regioselective C-2 silyl protection. Removal of the protecting group was then accomplished under mild conditions allowing for a straightforward preparation of C-5 monosubstituted and C-4,5 disubstituted oxazoles. The first practical C-2 protecting group of oxazoles has been demonstrated.

Lithium↗