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Letters in Organic Chemistry

Volumn 2, Issue 7, 2005, Pages 665-667

Exploration of synthetic pathways to unprecedented terpenyl thioglycosides

(4) Bourgeois, Marie Josèphe a Gueyrard, David b,c Montaudon, Evelyne a Rollin, Patrick b

a UNIVERSITÉ DE BORDEAUX (France)

b UNIVERSITÉ D'ORLÉANS (France)

c UNIVERSITÉ LYON 1 (France)

Author keywords

Carbohydrates; Monoterpenes; Thioglycosides

Indexed keywords

EID: 46249114911 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/157017805774296984 Document Type: Review

Times cited : (1)

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- Pinen-10-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (3):syrup,[α]D, 48(c=1, CHCl3, 1H-NMR (CDCl3) δ 0.81 (s, 3H, H-9′, 1.20 (d, 1H, Jgem, 10.6, H-7′a, 1.25 (s, 3H, H-8′, 1,95, 2.02, 2.12 (3s, 12H, OAc, 2.07-2.18 (m, 2H, H-5′, H-7′b, 2.24 (m, 2H, H-4′, 2.36 (m, 1H, H-1′, 3.08 and 3.35 (2d, 2H, Jgem, 14.0, H-10′, 3.88 (t, 1H, J, 8.4, H-5, 4.08 (dd, 1H, Jgem, 12.0, H-6a, 4.15 (dd, 1H, H-6b, 4.46 (d, 1H, J1,2, 10.1, H-1, 5.00 (dd, 1H, J2,3, 10.1, J3,4, 4.0, H-3, 5.23 (t, 1H, H-2, 5.36 (bs, 1H, H-3′, 5.40 (d, 1H, H-4, 13C NMR (CDCl3) δ 20.5, 20.6, 20.7 (CH3CO, 21.4 (C-9′, 26.0 (C-8′, 31.2 (C-4′, 31.6 (C-7′, 35.7 (C-10′, 37.8 C-6′, 40
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- 2′S)-3′-Oxopinan-10′-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (5, syrup, α]D, 7 (c, 1, CHCl3) 1H NMR (CDCl3) δ 0.78 (s, 3H, H-9′, 1.11 (d, 1H, Jgem, 10.4, H-7′b, 1.25 (s, 3H, H-8′, 1.90, 1.95, 2.00, 2.10 (4s, 12H, OAc, 2.41-2.63 (m, 7H, H-1′, H-2′, H-4′, H-5′, H7′a, H-10′b, H-2′, 3.36 (dd, 2H, Jgem, 13.1, Jvic, 3.0, H-10′a, 3.88 (t, 1H, J5,6, 6.7, H-5, 4.02 (d, 2H, H-6, 4.49 (d, 1H, J1,2, 9.8, H-1, 4.97 (dd, 1H, J2,3, 10.1, J3,4, 3.4, H-3, 5.12 (dd, 1H, H-2, 5.35 (d, 1H, H-4, 13 C NMR (CDCl3) δ 20.4, 20.5, 20.6 (CH3CO, 21.7 (C-9′, 26.6 (C-8′, 32.3 (C-7′, 33.8 (C-10′, 38.5 (C-5′, 38.8 C-6′
- +).

24
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26
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- Paramenth-1-en-10-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (6, syrup [α]D, 40 (c, 1, CHCl3) 1H NMR (CDCl3) δ 0.88 and 0.89 (2d, 6H, Jvic, 6.7, H-8′ and H-9′, 1.12-2.15 (m, 8H, H-3′, H.4′, H-5′, H-6′, H-7′, 1.96, 2.03, 2.04, 2.13 (4s, 12H, OAc, 3.10 and 3.35 (AB system, 2H, Jgem, 12.8, H-10′, 3.83 (td, 1H, J5,6, 6.6, J4,5, 0.9, H-5, 4.09-4.13 (m, 2H, H-6, 4.38 (d, 1H, J1,2, 10.1, H-1, 5.03 (dd, 1H, J2,3, 9.8, J3,4, 3.3, H-3, 5.23 (dd, 1H, J2,3, 9.8, J1,2, 10.1, H-2, 5.40 (dd, 1H, J3,4, 3.3, J4,5, 0.9, H-4, 5.60 (m, 1H, H-2′, 13C NMR (CDCl3) δ 19.6, 19.9 C-8′ and C-9′, 20.5, 20.6, 20.8
- +).

27
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28
- 46249126856
- 2′R,3′S)-Epoxypinan-10-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (8, To a solution of thiol 1 (182 mg, 0.5 mmol) in toluene (1mL, tert-butyl trans-pinocarveyl peroxide (112 mg, 1eq, was added and the mixture maintained at 80°C for 6h. After concentration in vacuo, the residue was purified by flash chromatography to furnish the desired compound (219mg, 85, as a syrup, α]D, 46 (c, 1, CHCl3, 1H NMR (CDCl3) δ 0.88 (s, 3H, H-9′, 1.25 (s, 3H, H-8′, 1.56 (d, 1H, Jgem, 9.7, H-7a′, 1.69 (in, 1H, H-5′, 1.92, 1.98, 2.02 and 2.09 (4s, 12H, OAc, 1.91-2.12 (m, 3H, H-4′, H-7′b, 2.20 (t, 1H, Jvic, 5.8, H-1′, 2.70 and 3.10 (AB system, 2H, Jgem, 14.6, H-10′, 3.30 (d, 1H, Jvic, 3.0, H-3′, 3.90 td, 1H, J5,6
- +).

29
- 46249109115
- 1R)-2,2-Dimethyl-3, 2,3,4,6-tetra-O- acetyl-1-thio-β-D-galactopyranosyl)methyl]cyclopent-3-enylethanal (9, syrup, α, 12 (c, 1, CHCl3, 1H NMR (CDCl3) δ 0.87 (s, 3H, gem Me, 1.03 (s, 3H, gem Me, 1.94, 2.00, 2.11 (3s, 12H, OAc, 2.22-2.59 (m. 5H. H-1′, H-5′, CH2CHO, 3.20 and 3.40 (AB system, 2H, Jgem, 14.2, CH2S, 3.88 (t, 1H, H-5, 4.00, 4.14 (ABX system, 2H, Jgem, 11.3, Jvic, 7.2, Jvic, 6.0, H-6, 4.45 (d, 1H, J1,2, 10.1, H-1, 5.03 (dd, 1H, J2,3, 10-1, J3,4, 3.3, H-3, 5.24 (t, 1H, H-2, 5.40 (m, 1H, H-4, 5.55 (m, 1H, H-4′, 9.80 (t, 1H, Jvic, 2.0, CHO, 13 C NMR (CDCl3) δ 20.5, 20.6, 20.7, 20.8, 20.9 (CH3CO and gem Me, 25.4 (gem Me, 26.3 CH2
- +).

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