1994
DOI: 10.1021/jo00103a054
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Bis[[4-(2,2-dimethyl-1,3-dioxolyl)]methyl]- carbodiimide (BDDC) and Its Application to Residue-Free Esterifications, Peptide Couplings, and Dehydrations

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Cited by 58 publications
(35 citation statements)
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“…In light of these results, we decided to use (S)-azide 18 directly instead of transforming it into hydrophobic compound 20. Treatment of 18 with either Na 2 S·9H 2 O [31] or more conveniently under Staudinger reaction conditions [30] accomplished the reduction of the azido function to afford the corresponding amine (S)-22 [32,33] in 70 % isolated yield in both cases. The amine 22 is very polar and inconvenient to handle on a small scale.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…In light of these results, we decided to use (S)-azide 18 directly instead of transforming it into hydrophobic compound 20. Treatment of 18 with either Na 2 S·9H 2 O [31] or more conveniently under Staudinger reaction conditions [30] accomplished the reduction of the azido function to afford the corresponding amine (S)-22 [32,33] in 70 % isolated yield in both cases. The amine 22 is very polar and inconvenient to handle on a small scale.…”
Section: Resultsmentioning
confidence: 99%
“…[31] Staudinger reaction: To a magnetically stirred solution of 18 (1.6 g, 10 mmol) in THF (20 mL) and water (four drops) was added Ph 3 P (3.1 g, 12 mmol) [ 33] +0.9°, c 1, CHCl 3 ; ref. [32] +1.48°, neat).…”
Section: (Rac)-3-n-benzamido-1-(triphenylmethyloxy)-2-propanol (5)mentioning
confidence: 99%
“…(2,2-Dimethyl-1,3-dioxolan-4-yl)methanamine (G0)-AEPGL-ipd (8) was synthesized from glycerol. [21] Scheme 2. Synthesis of polyether amine dendrons (G1 to G3).…”
Section: Resultsmentioning
confidence: 99%
“…34 To a stirred solution of 3-bromofuran (0.90 mL, General procedure A for preparation of malonates 19 To a stirred solution of the alcohol (100 mol%), mono-ethyl malonate (15a) 36 or mono-t-butyl malonate (15b) 8,36,37 (110 mol%) and DMAP (10 mol%) in CH 2 Cl 2 (0.5 M) at 0 °C was added DCC (120 mol%). After 1-2 h at rt, the mixture was filtered, washed twice with HCl (0.5 M) and sat.…”
Section: Methodsmentioning
confidence: 99%