Direct α-Selective glycosylations of acetyl-protected 2-deoxy- and 2,6-dideoxythioglycosides by preactivation protocol

Synlett

Volumn , Issue 10, 2010, Pages 1519-1524

  Lu, Yin Suo ^a,b   Li, Qin ^a,b   Wang, Yuan ^a,b   Ye, Xin Shan ^a,b  

^a PEKING UNIVERSITY   (China)

^b PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

2,6 dideoxysugars; 2 deoxyglycosides; Carbohydrate; Preactivation stereoselective glycosylation

Indexed keywords

2 DEOXYTHIOGLYCOSIDE; 2,6 DIDEOXYTHIOGLYCOSIDE; THIOGLYCOSIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONFORMATION; DRUG STRUCTURE; ENZYME ACTIVATION; GLYCOSYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

EID: 77953238348     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219943     Document Type: Article

References (64)

1. Kirschning A, Bechthold A F.-W, Rohr J, Top. Curr. Chem. 1997 188 1
2. Weymouth-Wilson A C., Nat. Prod. Rep. 1997 14 99
3. Butler M S., J. Nat. Prod. 2004 67 2141
4. Tavecchia P, Trumtel M, Veyrieres A, Sinaÿ P, Tetrahedron Lett. 1989 30 2533
5. Perez M, Beau [nl]J.-M, Tetrahedron Lett. 1989 30 75
6. Roush W R., Bennett C E., J. Am. Chem. Soc. 1999 121 3541
7. Blanchard N, Roush W R., Org. Lett. 2003 5 81
8. Roush W R., Sebesta D P., James R A., Tetrahedron 1997 53 8837
9. Thiem J, Schottmer B, Angew. Chem., Int. Ed. Engl. 1987 26 555
10. Marzabadi C H., Franck R W., Tetrahedron 2000 56 8385
11. Nicolaou K C., Ladduwahetty T, Randall J L., Chucholowski A, J. Am. Chem. Soc. 1986 108 2466
12. Zuurmond H M., vanderKlein P A. M., vanderMarel G A., vanBoom J H., Tetrahedron Lett. 1992 33 2063
13. Toshima K, Mukaiyama S, Nozaki Y, Inokuchi H, Nakata M, Tatsuta K, J. Am. Chem. Soc. 1994 116 9042
14. Rodríguez M A., Boutureira O, Matheu M I., Díaz Y, Castillón S, Eur. J. Org. Chem. 2007 2470
15. Lemieux R U., Morgan A R., Can. J. Chem. 1964 42 1473
16. Muller T, Schneider R, Schmidt R R., Tetrahedron Lett. 1994 35 4763
17. Binkley R W., Koholic D J., J. Org. Chem. 1989 54 3577
18. Tanaka H, Yoshizawa A, Takahashi T, Angew. Chem. Int. Ed. 2007 46 2505
19. Lear M J., Yoshimura F, Hirama M, Angew. Chem. Int. Ed. 2001 40 946
20. Jaunzems J, Sourkouni-Argirusi G, Jesberger M, Kirschning A, Tetrahedron Lett. 2003 44 637
21. Toshima K, Nozaki Y, Tatsuta K, Tetrahedron Lett. 1991 32 6887
22. Bielawska H, Michalska M, J. Carbohydr. Chem. 1991 10 107
23. Laupichler L, Sajus H, Thiem J, Synthesis 1992 1133
24. Mereyala H B., Kulkarni V R., Ravi D, Sharma G V. M., Rao B V., Reddy G B., Tetrahedron 1992 48 545
25. Morris W J., Shair M D., Org. Lett. 2009 11 9
26. Ito Y, Ogawa T, Tetrahedron Lett. 1987 28 2723
27. Li H, Chen M, Zhao K, Tetrahedron Lett. 1997 38 6143
28. Kim K S., Park J, Lee Y J., Seo Y S., Angew. Chem. Int. Ed. 2003 42 459
29. Yadav J S., Reddy B V. S., Reddy K B., Satyanarayana M, Tetrahedron Lett. 2002 43 7009
30. Sherry B D., Loy R N., Toste F D., J. Am. Chem. Soc. 2004 126 4510
31. Wang Y, Ye X.-S, Zhang L.-H, Org. Biomol. Chem. 2007 5 2189
32. Crich D, Sun S, J. Org. Chem. 1996 61 4506
33. Crich D, Sun S, J. Org. Chem. 1997 62 1198
34. Code J D. C., Van den Bos L J., Litjens R E. J. N., Overkleeft H S., Van Boom J H., Van der Marel G A., Org. Lett. 2003 5 1947
35. Yamago S, Yamada T, Maruyama T, Yoshida J.-I, Angew. Chem. Int. Ed. 2004 43 2145
36. Nguyen H M., Poole J L., Gin D Y., Angew. Chem. Int. Ed. 2001 40 414
37. Huang L, Wang Z, Li X, Ye X.-S, Huang X, Carbohydr. Res. 2006 341 1669
38. Huang L, Huang X, Chem. Eur. J. 2007 13 529
39. Huang X, Huang L, Wang H, Ye X.-S, Angew. Chem. Int. Ed. 2004 43 5221
40. Geng Y, Zhang L.-H, Ye X.-S, Chem. Commun. 2008 597
41. Geng Y, Zhang L.-H, Ye X.-S, Tetrahedron 2008 64 4949
42. Benakli K, Zha C, Kerns R J., J. Am. Chem. Soc. 2001 123 9461
43. Boysen M, Gemma E, Lahmann M, Oscarson S, Chem. Commun. 2005 3044
44. Manabe S, Ishii K, Ito Y, J. Am. Chem. Soc. 2006 128 10666
45. Lu Y.-S, Li Q, Zhang L.-H, Ye X.-S, Org. Lett. 2008 10 3445
46. For the use of carbonate functionality, also see, for example:, Crich D, Jayalath P, J. Org. Chem. 2005 70 7252
47. Crich D, Vinod A U., Picione J, J. Org. Chem. 2003 68 8453
48. Cotarca L, Delogu P, Nardelli A, Sunjic V, Synthesis 1996 553
49. Wang C, Wang H, Huang X, Zhang L.-H, Ye X.-S, Synlett 2006 2846
50. Burgey C S., Vollerthun R, Fraser-Reid B, J. Org. Chem. 1996 61 1609
51. Mootoo D R., Konradsson P, Udodong U, Fraser-Reid B, J. Am. Chem. Soc. 1988 110 5583
52. Zhu T, Boons G.-J, Org. Lett. 2001 3 4201; and references cited therein
53. Crich D, Sun S, Tetrahedron 1998 54 8321
54. Crich D, Smith M, J. Am. Chem. Soc. 2001 123 9015
55. Kim K S., Kim J H., Lee Y J., Lee Y J., Park J, [nl] J. Am. Chem. Soc. 2001 123 8477
56. Tanada S.-I, Takashima M, Tokimoto H, Fujimoto Y, Tanaka K, Fukase K, Synlett 2005 2325
57. Codee J D. C., Krock L, Castagner B, Seeberger P H., Chem. Eur. J. 2008 14 3987
58. Crich D, Sharma I, Org. Lett. 2008 10 4731
59. Crich D, Li L.-F, J. Org. Chem. 2009 74 773; and references cited therein
60. Manabe S, Ishii K, Hashizume D, Koshino H, Ito Y, Chem. Eur. J. 2009 15 6894
61. Lin S.-C, Chao C.-S, Chang C.-C, Mong K.-K T., Tetrahedron Lett. 2010 51 1910
62. Park J, Boltje T J., Boons G.-J, Org. Lett. 2008 10 4367
63. Xiong D.-C, Zhang L.-H, Ye X.-S, Adv. Synth. Catal. 2008 350 1696; and references cited therein
64. Typical Glycosylation Procedure Triflic anhydride (11.0 mL, 0.061 mmol) was added to a stirred solution of p-methylphenyl 3,4,6-tri-O-acetyl-2- deoxy-1-thio-a-D-galactopyranoside (1a, 30.0 mg, 0.076 mmol), benzenesulfinyl morpholine (BSM, 12.9 mg, 0.061 mmol), and 4 MS (350 mg, activated powder) in CH2Cl2 (3.0 mL) at 72 C under nitrogen atmosphere. The reaction mixture was stirred for 10 min. After loss of 1a detected by TLC, a solution of methyl 3-O-benzyl-4,6-O-benzylidene-a- D-glucopyranoside (2a, 18.8 mg, 0.051 mmol) in CH2Cl2 (0.5 mL) was added dropwise to the reaction mixture. The mixture was stirred for 30 min, and the reaction was quenched by Et3N (8.0 mL). The precipitate was filtered off, and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (PEEtOAc, 2.5:1) to give methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(3,4,6- tri-O-acetyl-2-deoxy-a-D- galactopyranosyl)-a-D-glucopyranoside (3a, 27.6 mg, 84% yield) as a foam. Rf = 0.35 (PEEtOAc, 1.5:1). 1H NMR (500 MHz, CDCl3): d = 7.50 (dd, 2 H, J = 2.0, 7.5 Hz), 7.407.33 (m, 7 H), 7.297.27 (m, 1 H), 5.60 (s, 1 H), 5.37 (ddd, 1 H, J = 3.0, 5.0, 12.5 Hz), 5.15 (d, 1 H, J = 3.0 Hz), 5.14 (d, 1 H, J = 3.5 Hz), 4.93 (d, 1 H, J = 10.5 Hz), 4.89 (d, 1 H, J = 3.5 Hz), 4.71 (d, 1 H, J = 10.5 Hz), 4.36 (t, 1 H, J = 6.5 Hz), 4.31 (dd, 1 H, J = 4.5, 10.0 Hz), 3.98 (t, 1 H, J = 9.5 Hz), 3.90 (dd, 1 H, J = 6.5, 11.0 Hz), 3.873.74 (m, 4 H), 3.65 (t, 1 H, J = 9.5 Hz), 3.43 (s, 3 H), 2.132.08 (m, 4 H), 2.00 (s, 3 H), 1.961.92 (m, 4 H). 13C NMR (125 MHz, CDCl3): d = 170.13, 170.23, 169.79, 138.06, 137.26, 128.96, 128.54, 128.47, 128.25, 127.86, 125.95, 101.27, 97.12, 94.10, 82.71, 76.85, 75.74, 73.45, 69.00, 66.61, 65.87, 62.25, 61.87, 55.23, 29.86, 20.81, 20.70. MS (ESI-TOF, positive): m/z = 667 [M + Na]+. Anal. Calcd for C33H40O13: C, 61.48; H, 6.25. Found: C, 61.65; H, 6.40.