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Deprotection of t-Butyldimethylsiloxy (TBDMS) Protecting Group with Catalytic Copper (II) Chloride Dihydrate

ISSN:1001-8417
2000年第9期
Zhong Ping TAN, Lin WANG, Jian Bo WANG Department of Chemistry,Peking University,Beijing 100871 Zhong Ping TAN, Lin WANG, Jian Bo WANG
Zhong Ping TAN; Lin WANG; Jian Bo WANG Department of Chemistry,Peking University,Beijing 100871 Zhong Ping TAN, Lin WANG, Jian Bo WANG Department of Chemistry,Peking University,Beijing 100871

The protection of functional group is unavoidable in multi-step organic synthesis. Alongwith tetrahydropyranyl (THP) ethers, t-butyldimethylsilyl (TBDMS) ethers have beenwidely used for protecting hydroxyl groups. TBDMS ether is more stable to hydrolysisthan trimethylsilyl ether, but is still readily cleaved by a variety of selective conditionsl.The deprotection of TBDMS is usually under mild acidic conditions [AcOH/H,O/THF,3t l: l', or BF, Et,O/CHCI,', etc. '], or with a fluoride…


t-Butyldimethylsilyl (TBDMS) ether can be cleaved upon refluxing in acetone/H_2O (95: 5) in the presence of a catalytic amount of copper (II) chloride dihydrate (5 mmol %).

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ISSN:1001-8417
2000年第9期

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