Transient silylation of the guanosine O6 and amino groups facilitates N-acylation

Organic Letters

Volumn 6, Issue 15, 2004, Pages 2555-2557

  Fan, Yupeng ^a   Gaffney, Barbara L ^a   Jones, Roger A ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ACETYL CHLORIDE; ALCOHOL; GUANOSINE; METHYLAMINE; PHENOXYACETYL CHLORIDE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; DEPROTECTION REACTION; NITROGEN NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RNA SYNTHESIS; SILYLATION; SYNTHESIS;

AMINOACYLATION; GUANOSINE; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXYGEN; SILANES;

EID: 4043140255     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049096i     Document Type: Article

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23. The very small amount of TMSC1 used was difficult to measure accurately; therefore, 10 equiv is only approximate and should be regarded as an upper limit.
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25. 1H NMR (DMSO, 300 MHz): δ 11.83 (s, 1H), 11.78 (s, 1H), 8.29 (s, 1H), 7.35-7.28 (m. 2H), 7.02-6.95 (m, 3H), 5.82 (d, J = 5.7 Hz. IH), 5.70-4.90 (br, 3H), 4.87 (s, 2H), 4.45 (t,./ = 5.3 Hz, IH), 4.14 (t, J = 4.2 Hz, IH), 3.92 (q, J = 3.9 Hz, IH), 3.65 (dd, ./ = 12 Hz,./ = 4.2 Hz, IH), 3.55 (dd, J= 12 Hz, J = 4.1 Hz, IH). 13CNMR(DMSO, 75.4MHz): ô170.8, 157.4, 154.8, 148.5, 147.2, 137.7, 129.4, 121.2, 120.3, 114.4, 86.7, 85.3, 74.0, 70.2, 66.2, 61.1. Anal. Calcd for C18H19N5O7: C, 51.80; H. 4.59; N, 16.78. Found: C, 51.62; H, 4.42; N, 16.42.
26. 1H NMR (CDCl3, 400 MHz): ô11.74 (s, IH), 8.91 (s, IH), 7.70 (s, IH), 7.36 (m, 2H), 7.10 (m, IH), 6.96 (m, 2H), 5.81 (s, IH), 4.69 (s, 2H), IH), 7.36 (m, 2H), 7.10 (m, IH), 6.96 (m, 2H), 5.81 (s, IH), 4.69 (s, 2H), 4.50 (dd, J = 9.2 Hz, J = 5.2 Hz, IH), 4.39 (d, J = 4.4 Hz, IH), 4.21 (td, ~(t, J = 9.8 Hz, IH), 1.02 (s, 9H), 1.01 (s, 9H), 0.93 (s, 9H), 0.14 (s, 3H), (t, J = 9.8 Hz, IH), 1.02 (s, 9H), 1.01 (s, 9H), 0.93 (s, 9H), 0.14 (s, 3H), J = 10 Hz, J = 5.2 Hz, IH), 4.12 (dd,./ = 9.6 Hz, J = 4.4 Hz, IH), 4.00 (t, J = 9.8 Hz, IH), 1.02 (s, 9H), 1.01 (s, 9H), 0.93 (s, 9H), 0.14 (s, 3H), 0.13 (s, 3H). 13C NMR (CDCl3, 75.4 MHz): ô169.4, 156.3, 155.2, 146.9, (t, J = 9.8 Hz, IH), 1.02 (s, 9H), 1.01 (s, 9H), 0.93 (s, 9H), 0.14 (s, 3H), (t, J = 9.8 Hz, IH), 1.02 (s, 9H), 1.01 (s, 9H), 0.93 (s, 9H), 0.14 (s, 3H), 146.2, 136.7, 130.2, 123.4, 122.8, 114.9,92.2,76.3,76.1,74.8,68.0,67.2. 27.7, 27.3, 26.2, 23.1, 20.7, 18.7, -3.8, -4.6. Anal. Calcd for C32H49N5O7-Si2: C, 57.20; H, 7.35; N, 10.42. Found: C, 56.80; H, 7.30; N, 10.23.