✦ LIBER ✦
Self-sacrificing acetylation observed during attempted desilylation of 1-[4-benzenesulfonyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-5-O-methanesulfonyl-α-l-threo-pentofuranosyl]thymine
✍ Scribed by Hisashi Shimada; Yutaka Kubota; Hiromichi Tanaka
- Book ID
- 104097962
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- French
- Weight
- 310 KB
- Volume
- 51
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Desilylation of 1-[4-benzenesulfonyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-5-O-methanesulfonyl-a-Lthreo-pentofuranosyl]thymine (4) with Bu 4 NF/THF, when carried out at room temperature, gave four products. Among these, there were 1-[3-O-acetyl-4-benzenesulfonyl-2-deoxy-5-O-methanesulfonyl-a-L-threo-pentofuranosyl]thymine (7) and thymine. A possible reaction mechanism is proposed, which suggests the origin of 3 0 -O-acetyl group of 7 and thymine as well as structures of the other two products (9a and 9b).