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Journals / Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi / 2026 / Cilt: 21 Sayı: 62

Mono- and Di-Sulfonate Esters of -L-Arabinochloralose; 3-O-Protected-5-Azido and 5-O-Alkyl Derivatives

β-L-Arabinokloraloz’un Mono- ve Di-Sülfonat Esterleri; 3-O-Korunmuş-5-Azido ve 5-O-Alkil Türevleri

Nilgün Yenil0000-0002-9611-6424
Pages
659–668
Publication Date
2019-05-21
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

All newly synthesized molecules were structurally characterized by using spectroscopic techniques (IR, NMR and Mass).

📌 3 Key Takeaways

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Objective & Hypothesis:In this research, it was aimed to synthesize the organic compounds containing di-mesylate (methane sulfonate) and di-tosylate ester groups on the simple monosaccharide skeleton and mono-mesylate and mono-tosylate organic derivatives including azido groups in the primer position.
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Key Findings & Data:After the reaction of this monosaccharide unit with chloral in the presence of concentrated H 2 SO 4 , 1,2- O-(S)- trichloroethylidene-β- L -arabinofuranose was firstly obtained.
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Conclusion & Impact:All newly synthesized molecules were structurally characterized by using spectroscopic techniques (IR, NMR and Mass).
🔬Design:Araştırma Makalesi
📍Scope:Comprehensive Sample
⚙️Variables:Arabinoz · Azit · Furanoz

Abstract

In this research, it was aimed to synthesize the organic compounds containing di-mesylate (methane sulfonate) and di-tosylate ester groups on the simple monosaccharide skeleton and mono-mesylate and mono-tosylate organic derivatives including azido groups in the primer position. In this target, β- L -arabinofuranose was chosen as the starting sugar. After the reaction of this monosaccharide unit with chloral in the presence of concentrated H 2 SO 4 , 1,2- O-(S)- trichloroethylidene-β- L -arabinofuranose was firstly obtained. The ester derivatives, 3,5-di- O- mesyl (di-mesylate) and 3,5-di- O -tosyl (di-tosylate), were then synthesized on this sugar skeleton protected with trichloroethylidene acetal ring. 5-Azido-3- O -mesyl and 5-azido-3- O -tosyl derivatives of these di-mesylate and di-tosylate ester derivatives were subsequently obtained under appropriate reaction conditions. Furthermore, the mono-tosylate ester derivative of 1,2- O-(S)- Trichloroethylidene-β- L -arabinofuranose was reacted with methyl iodide in the presence of silver oxide to obtain the corresponding 5- O- tosil-3- O -methyl derivative. This obtained derivative was converted to the 5-Azido-3- O -methyl derivative under suitable reaction conditions. In addition, the 1,2- O-(S)- Trichloroethylidene-β- L -arabinofuranose was reacted with trityl chloride to produce the corresponding 5- O -trityl derivative. The 5- O -Trityl-3- O -methyl arabinochloralose was synthesized by the methylation reaction of 5- O -trityl derivative. Thus, the secondary hydroxyl group of the carbohydrate skeleton unit is protected by methyl group in the 5- O -tosyl and 5- O -trityl derivatives. All newly synthesized molecules were structurally characterized by using spectroscopic techniques (IR, NMR and Mass).

Özet

Bu araştırmada, basit monosakkarit iskeleti üzerinde di-mesilat (metan sülfonat) ve di-tosilat ester grupları ile primer pozisyonda azido gruplarının bulunduğu mono-mesilat ve mono-tosilat yapılı organik türevlerin sentezi hedeflenmiştir. Bu hedef doğrultusunda, β- L -Arabinofuranoz başlangıç şekeri olarak seçilmiştir. Bu monosakkarit biriminin kloral ile derişik H 2 SO 4 varlığındaki tepkimesi sonrası 1,2- O-(S) -Trikloroetiliden-β- L -arabinofuranoz elde edilmiştir. Daha sonra, trikloroetiliden asetal halkası ile korunmuş olan bu şekerin iskelet yapısı üzerinde öncelikle 3,5-Di- O -mesil (di-mesilat) ve 3,5-di- O -tosil (di-tosilat) gruplarının var olduğu ester türevleri sentezlenmiştir. Devamında, uygun reaksiyon koşullarında bu di-mesilat ve di-tosilat ester türevlerinden 5-Azido-3- O -mesil ve 5-azido-3- O -tosil türevleri elde edilmiştir. Ayrıca, 1,2- O-(S) -Trikloroetiliden-β- L -arabinofuranoz’un mono-tosilat ester türevi, ilgili 5- O -tosil-3- O -metil türevini elde etmek için gümüş oksit varlığında metil iyodür ile reaksiyona sokulmuştur. Elde edilen bu türev uygun reaksiyon koşullarında 5-Azido-3- O -metil türevine dönüştürülmüştür. İlaveten, 1,2- O-(S) -Trikloroetiliden-β- L -arabinofuranoz ilgili 5- O -tritil türevi elde etmek için tritil klorür ile reaksiyona sokulmuştur. 5- O -Tritil türevinin metilleme reaksiyonuyla 5- O -tiritil-3- O -metil arabinokloraloz sentezlenmiştir. Böylelikle, 5- O -Tosil ve 5- O -tiritil türevlerinde, karbohidrat iskelet biriminin sekonder hidroksil grubu metil grubu ile korunmuştur. Sentezlenen tüm yeni moleküller spektroskopik teknikler (IR, NMR ve Kütle) kullanılarak yapısal olarak karakterize edilmiştir.

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Cite This Article

Yenil, N. (2019). Mono- and Di-Sulfonate Esters of -L-Arabinochloralose; 3-O-Protected-5-Azido and 5-O-Alkyl Derivatives. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi, Cilt: 21 Sayı: 62, 659–668. https://doi.org/10.21205/deufmd.2019216228

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