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Synlett

Volumn , Issue 8, 2008, Pages 1225-1229

Efficient synthesis of α- and β-2′-deoxy-heteroaryl-C- nucleosides

(3) Spadafora, Marie a Burger, Alain a Benhida, Rachid a

a UNIVERSITÉ CÔTE D'AZUR (France)

Author keywords

Aryl aldol condensation; C nucleosides; Cycloetherification

Indexed keywords

4 TOLUENE SULFONIC ACID; ALPHA 2' DEOXY HETEROARYL C NUCLEOSIDE; BETA 2' DEOXY HETEROARYL C NUCLEOSIDE; C NUCLEOSIDE; SULFONIC ACID DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ETHERIFICATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 44449178388 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072589 Document Type: Article

Times cited : (9)

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30
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31
- 44449171401
- Typical Procedure To a solution of benzofuran (2 mmol) in anhyd THF (6 mL) was added dropwise n-BuLi (1.6 M in hexane, 2 mmol) at 0°C. The mixture was stirred for 30 min and aldehyde 1 (412 mg, 1 equiv) in anhyd THF (2 mL) was slowly added. The reaction was stirred during 90 min and warmed slowly to r.t, then quenched with a cold solution of NH 4Cl and extracted with CH2Cl2 (3 x 40 mL, The combined organic layers were dried (MgSO4) and evaporated under reduced pressure to give a crude oil. Silica gel column chromatography purification using gradient elution [cyclohexane (100, to EtOAc-cyclohexane (8:92, afforded (S)-2a and (R)-2a as yellow oils (440 mg, 83, R/S, 35:65, Compound (S)-2a: TLC (cyclohexane-EtOAc, 7:3, Rf, 0.49. 1H NMR (200 MHz, CDCl3, δ, 0.95 (s, 9 H, t- Bu, 1.28 s, 3 H, CH3, 1.37
- +], 450.7.

32
- 44449086932
- All products gave satisfactory spectral data. Data for selected products are given here. Compound (R,S)-2b: TLC (cyclohexane-EtOAc, 7:3, Rf, 0.70-0.75. 1H NMR (200 MHz, CDCl3, δ, 1.04 (s, 9 H, t-Bu, 1.34 (s, 3 H, CH3, 1.41 (s, 3 H, CH3, 1.50-2.2 (m, 2 H, H-2prime;, 3.68-3.71 (m, 2 H, 2 x H-5′, 4.21-4.42 (m, 2 H, H-4′, H-3′, 4.88-4.95 (m, 1 H, H-1′, 6.25-6.26 (m, 2 H, 2 x H-Ar, 7.38-7.41 (m, 7 H, 6 x H-Ph, 1 x H-Ar, 7.62-7.66 (m, 4 H, 4 x H-Ph) ppm. 13C NMR (50 MHz, CDCl 3, δ, 19.29 (Me3C, 25.66 (Me 2C, 26.93 (Me3C, 28.14 (Me2C, 35.40 (C-2′, 62.43 (C-5′, 67.64-65.66 (C-1′, 76.54-74.36 (C-3′, 77.18 (C-4′, 106.01-108.69 (C-Ar, 108.83 (Me 2C, 110.26-111.95 (C-Ar, 127.91, 129.96, 133.17, 135.70, 142.03 C-Ph and C-Ar
- +].

33
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- Jiang, Y.L.¹ Stivers, J.T.²

34
- 44449162983
- General Procedure To a solution of 2a (R or S, 1 mmol) in toluene (25 mL) was added PTSA (0.2 mmol, 0.2 equiv, The mixture was stirred at 50°C for 4 h then quenched with a sat. soln of NaHCO3 and extracted with CH2Cl2 (3 x 30 mL, The combined organic layers were dried over MgSO4 and evaporated under reduced pressure to give a crude oil. Silica gel column chromatography purification using gradient elution [cyclohexane (100, to EtOAc-cyclohexane (20:80, afforded 3a as a yellow oil. Compound α-3a: TLC (cyclohexane-EtOAc, 7:3, Rf, 0.43. 1H NMR (200 MHz, CDCl3, δ, 1.08 (s, 9 H, t-Bu, 2.27-2.39 (m, 1 H, H-2′, 2.66-2.80 (m, 1 H, H-2′, 3.69-3.88 (m, 2 H, 2 x H-5′, 4.16-4.20 (m, 1 H, H-4′, 4.52-4.59 (m, 1 H, H-3′, 5.24-5.31 (dd, 1 H, J, 8.0, 5.3 Hz, H-1′, 6.69 s, 1 H, H-furan, 7.39-7.66
- +].

35
- 44449100200
- Compound α-4a: TLC (CH2Cl2-MeOH, 98:2, Rf, 0.3. 1H NMR (500 MHz, CDCl 3, δ, 2.33-2.37 (m, 1 H, H-2′, 2.61-2.64 (m, 1 H, H-2′, 3.73-3.76 (m, 2 H, 2 x H-5′, 4.01-4.04 (q, 1 H, J, 4.7 Hz, H-4′, 4.43-4.45 (q, 1 H, J, 5.7 Hz, H-3′, 5.21 (t, 1 H, J, 6.9 Hz, H-1′, 6.67 (s, 1 H, H-furan, 7.16-7.20 (t, 1 H, J, 7.2 Hz, H-Ar, 7.22-7.25 (m, 1 H, H-Ar, 7.42 (d, 1 H, J, 8.2 Hz, H-Ar, 7.50 (d, 1 H, J, 7.6 Hz, H-Ar) ppm. 13C NMR (CDCl3, 125 MHz, δ, 39.23 (C-2′, 58.74 (C-5′, 62.74 (C-3′, 73.23 (C-1′, 85.69 (C-4′, 103.95 (C-3, 111.35 (C-7, 121.85 (C-4, 122.87 (C-5, 124, C-6, 128.15 (C-Ar, 154.75 (C-Ar, 157.30 (C-2) ppm. MS ESI, m/z, 256.7 [MNa, 241.9 [MLi, 214.7 [M, H2O, Compound
- 2O].

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