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Volumn , Issue 2, 2007, Pages 303-307

A serendipitous discovery of a new C-furanosyl glycine synthesis via thiazole-based aminohomologation of hexopyranoses

Author keywords

Amino acids; Cyclization; Glycopeptides; Glycosides; Ring closure

Indexed keywords

AMINO ACID; C FURANOSYL GLYCINE DERIVATIVE; GALACTOSE; GLUCOSE; GLYCINE DERIVATIVE; HEXOPYRANOSE DERIVATIVE; MANNOSE; MONOSACCHARIDE; THIAZOLE; UNCLASSIFIED DRUG;

EID: 33847046794     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-967993     Document Type: Article
Times cited : (8)

References (36)
  • 3
    • 28044439641 scopus 로고    scopus 로고
    • For recent references 2000-2005, see
    • (b) For recent references (2000-2005), see: Dondoni, A.; Massi, A.; Sabbatini, S. Chem. Eur. J. 2005, 11, 7110.
    • (2005) Chem. Eur. J , vol.11 , pp. 7110
    • Dondoni, A.1    Massi, A.2    Sabbatini, S.3
  • 15
    • 33847075789 scopus 로고    scopus 로고
    • The open-chain amino alcohol 1 was obtained by reduction of the minor product that was formed by addition of thiazolylmagnesium bromide to the sugar hydroxylamine-nitrone mixture derived from the reaction of N- benzylhydroxylamine with tetra-O-benzyl-D-mannopyranose.
    • The open-chain amino alcohol 1 was obtained by reduction of the minor product that was formed by addition of thiazolylmagnesium bromide to the sugar hydroxylamine-nitrone mixture derived from the reaction of N- benzylhydroxylamine with tetra-O-benzyl-D-mannopyranose.
  • 19
    • 33847049798 scopus 로고    scopus 로고
    • For a critical discussion on this issue, see section IIA in ref. 2a.
    • For a critical discussion on this issue, see section IIA in ref. 2a.
  • 20
    • 33847058784 scopus 로고    scopus 로고
    • 3 reagent withdrawn from freshly opened commercially available vials (Fluka 14010).
    • 3 reagent withdrawn from freshly opened commercially available vials (Fluka 14010).
  • 22
    • 33847019969 scopus 로고    scopus 로고
    • Typical Procedure for Entry N-Boc-Amines 5a-c, 7a-c. To a stirred solution of N-benzyl-N-glycosylhydroxylamines 4a-c, 6a-c (0.50 g, 0.69 mmol) in MeOH (9.0 mL) was added a 12% HCl solution of TiCl 3 (1.22 mL, 1.71 mmol, Stirring was manteined for an additional 15 min at r.t, then 5 M NaOH was added dropwise until pH 7 (the solution became white, After stirring for an additional 5 min, the primary amine was extracted with EtOAc (3 x 25 mL, The organic phase was washed with brine (2 x 20 mL, dried over Na2SO4, and concentrated. Crude primary amine was dissolved in dioxane (6.0 mL) and BoC2O (330 mg, 1.50 mmol) was added in one portion. Then some drops of a sat. solution of NaHCO3 were added to the mixture until pH 7.5. Stirring was mantained for 18 h, then the reaction was quenched with a 10% citric acid solution (4.0 mL, The protected amine was extracted with EtOAc 2 x 20 mL, The combined organic
    • 6S: C, 71.16; H, 6.82; N, 3.95. Found: C, 71.17; H, 6.79; N, 3.97.
  • 23
    • 0011932271 scopus 로고    scopus 로고
    • Loupy, A, Ed, Wiley-VCH: Weinheim
    • (a) Microwaves in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: Weinheim, 2002.
    • (2002) Microwaves in Organic Synthesis
  • 25
    • 33847037901 scopus 로고    scopus 로고
    • Typical Procedure for Entry C-Furanosides 8a,b, 9a-c, 14. To a cooled (0 °C, stirred solution of N-Boc-protected amines 5a-c, 7a-c, 13 (175 mg, 0.24 mmol) in pyridine (6.0 mL) was added mesyl cloride (56 μL, 0.72 mmol) in one portion. The mixture was stirred for an additional 2 h, then some drops of MeOH were added and the solvent was removed in vacuo. The residue was taken up in EtOAc (10 mL) and washed with a sat. solution of NaHCO3 (2 x 10 mL, The organic layer was dried over Na 2SO4, filtered, and concentrated. A 0.5-2.0 mL process vial was filled with the above crude mesylated intermediate, DIPEA (83 μL, 0.48 mmol, and anhyd DMF 2.0 mL, The vial was sealed with the Teflon septum and aluminium crimp by using an appropriate crimping tool. The vial was then placed in its correct position in the Biotage Initiator cavity where irradiation for 20 min at 150°C was performed. After the full irradiation sequence was complete
    • 6S: C, 68.16; H, 6.54; N, 4.54. Found: C, 68.22; H, 6.60; N, 4.59.
  • 31
    • 33847036281 scopus 로고    scopus 로고
    • Typical Procedure for Entry C-Glycosyl Glycines 10a,b, 11a-c, 15. A mixture of the thiazole derivative 8a,b, 9a-c, 14 (164 mg, 0.26 mmol, activated 4 Å MS (400 mg) and MeCN (4.0 mL) was stirred at r.t. for 10 min then methyl triflate (32 μL, 0.28 mmol) was added in one portion. The suspension was stirred for an additional 15 min then the solvent was removed under reduced pressure. The residue was taken up in MeOH (4.0 mL, cooled to 0°C and treated with NaBH4 (22 mg, 0.56 mmol, The mixture was stirred at r.t. for 15 min, diluted with acetone, filtered through a pad of Celite®, and concentrated in vacuo. The residue was taken up in 10:1 MeCN-H2O (4.0 mL) and then treated with CuO (60 mg, 0.78 mmol, and CuCl2·2H2O 48 mg, 0.28 mmol, The resulting suspension was stirred at r.t. for 10 min, then filtered through a pad of Celite® and concentrated in vacuo at a temperature below 30°C. The residue wa
    • 8: C, 69.02; H, 6.98; N, 2.37. Found: C, 69.04; H, 6.97; N, 2.37.
  • 32
    • 33847067828 scopus 로고    scopus 로고
    • Compound 11a: [α]D 27.9 (c 0.3, CHCl 3, 1H NMR (C6D6, δ, 7.25-7.00 (m, 15 H, 3 Ph, 5.94 (d, 1 H, JNH,2, 6.5 Hz, NH, 4.92 (dd, 1 H, J2,NH, 6.5 Hz, J2,3, 5.0 Hz, H-2, 4.45 and 4.15 (2 d, 2 H, J, 12.0 Hz, CH2Ph, 4.35-1.20 (m, 7 H, 2 CH2Ph, H-3, H-4 and H-6, 3.83 (br s, 1 H, H-5, 3.79 (dd, 1 H, J7a,6, 6.5 Hz, J7a,7b, 10.0 Hz, H-7a, 3.68 (dd, 1 H, J7b,6, 5.5 Hz, J 7b,7a, 10.0 Hz, H-7b, 3.22 (s, 3 H, CH3, 1.35 (s, 9 H, t-Bu, Compound 10b: [α]D 10.9 (c 1.0, CHCl3, 1H NMR (C6D6, δ, 7.25-7.00 (m, 15 H, 3 Ph, 5.42 (d, 1 H, JNH,2, 8.5 Hz, NH, 4.92 dd, 1 H, J2,NH, 8.5 Hz, J2,3, 4.5 Hz
    • 7b,7a = 10.0 Hz, H-7b), 1.39 (s, 9 H, t-Bu).
  • 33
    • 33847050573 scopus 로고    scopus 로고
    • Cyclization of the N-Boc amino alcohol 7c required two cycles of microwave irradiation to get an acceptable yield of the C-furanoside 9c. On the other hand, microwave irradiation of 5c for prolonged time periods (single or repeated cycles) did not afford the corresponding furanoside 8c.
    • Cyclization of the N-Boc amino alcohol 7c required two cycles of microwave irradiation to get an acceptable yield of the C-furanoside 9c. On the other hand, microwave irradiation of 5c for prolonged time periods (single or repeated cycles) did not afford the corresponding furanoside 8c.
  • 36
    • 33847071179 scopus 로고    scopus 로고
    • 4 at lower temperatures and by L-Selectride (THF, -78°C) afforded the undesired alcohol 7b as major product.
    • 4 at lower temperatures and by L-Selectride (THF, -78°C) afforded the undesired alcohol 7b as major product.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.