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产品名称: 二碳酸二叔丁酯

产品分类: 多肽试剂

产品目录: 10102


产品质量标准

产品名称

二碳酸二叔丁酯,Boc酸酐

英文名

Boc Anhydride; Di-tert-butyl dicarbonate; DiBoc; Di-tert-butyl pyrocarbonate; Dicarbonic acid bis(1,1-dimethylethyl)ester; Pyrocarbonic acid di-tert-butyl ester

CAS序号 24424-99-5
分子式 C10H18O5
分子量 218.25
外观 无色液体或半固体
熔点 20~25 ℃
纯度(GC) 不低于99%
包装 100ml/瓶;500ml/瓶;1000ml/瓶;50公斤/桶;180公斤/桶
贮存 阴凉干燥处保存;瓶装产品长期放置会产生较多气体,开启瓶盖时应注意防护!

小注:

Reagent for amino group protection as the t-butyl carbamate (t-butoxycarbonyl, Boc derivatives), in high yield under mild conditions, widely used in peptide chemistry [1,2] .
Benzyl carbamates(Cbz, Z) may be transformed into Boc in a one pot procedure catalysed by Pd/C [3] .
Amides can be protected in the presence of a catalytic quantity of DMAP [4,5] ; the amide link of the product undergoes facile alkaline hydrolysis or methanolysis. The nitrogen function of indoles and pyrroles can also be protected under similar conditions [6,7] . 1-Boc indoles may be synthesized from N-Boc 2-alkyl aniline [8] .
The Boc group is readily cleaved with acid, most often Trifluoroacetic acid.
In the presence of 1 equivalent of DMAP in acetonitrile, arylamines are converted to isocyanates, generally in high yield; the dicarbonate here behaves as a convenient phosgene replacement [9] . The same reagent system has also been applied nitroalkanes for the ambient temperature generation of nitrile oxides which were trapped in situ with dipolarophiles [10] .
Feature on uses of this reagent in synthesis was reveiwed [11] .

Ref:

  1. Org.Synthe.Coll., 1990, 7, 70
  2. Synthesis, 223 (1987): Org.Synthe.Coll., 1998, 9, 124, 300
  3. Tetrahedron Lett., 1992, 33, 3167
  4. J. Org.Chem., 1983,48, 2424
  5. Acta Chem. Scand.B, 1986, 40, 745
  6. J.Chem.Soc., Chem. Commun., 1984, 1699
  7. Org.Synth.Coll., 1998, 9, 121
  8. Synthesis, 1991, 871
  9. Angew, Chem.Int.Ed., 1995, 34, 2497
  10. Synthesis, 1997, 309
  11. Synlett, 2001, 1995
 
 

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