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Synlett

Volumn , Issue 3, 2009, Pages 425-428

α-Selective sialylations with N-acetyl-5-N,4-O-oxazolidinone- protected p-toluenethiosialoside

(3) Liang, Fen Fen a Chen, Li a Xing, Guo Wen a

a BEIJING NORMAL UNIVERSITY (China)

Author keywords

Oxazolidinone; p toluenethiosialoside; Sialic acid

Indexed keywords

EID: 62249104475 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087539 Document Type: Article

Times cited : (35)

References (35)

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32
- 62249169714
- Donor 1 was prepared similarly as literature described. 14 Compound characterization data for 5: 1H NMR (500 MHz, CD3OD, δ, 7.47 (d, J, 7.7 Hz, 2 H, 7.22 (d, J, 7.7 Hz, 2 H, 4.06 (dt, J, 11.9, 3.3 Hz, 1 H, 3.83 (m, 3 H, 3.67-3.69 (m, 2 H, 3.67 (s, 3 H, 3.55 (d, J, 8.8 Hz, 1 H, 3.14 (dd, J, 11.7, 3.6 Hz, 1 H, H-3eq, 2.38 (s, 3 H, 2.21 (t, J, 12.2 Hz, 1 H, H-3ax, 13C-APT NMR (125 MHz, CD3OD, δ, 169.1, 160.9, 140.5, 136.3, 129.3, 125.1, 87.8, 78.3, 78.2, 71.5, 70.0, 63.1, 57.1, 52.2, 36.6, 19.9. HRMS: m/z calcd for C 18H23NO8SNa [M, Na, 436.10421; found. 436.10364. Compound 1: 1H NMR (500 MHz, CDCl 3, δ, 7.45 (d, J, 7.9 Hz, 2 H, 7.18 (d, J, 7.9 Hz, 2 H, 5.55 (d, J, 5.8 Hz, 1 H, 5.38 (m, 1 H, 4.45 dd, J, 12.2, 2.6 Hz, 1 H
- +: 604.14647; found. 604.14590.

33
- 62249089935
- General Sialylation Procedure (with the Coupling Between 1 and 6 as Example) To a mixture of donor 1 (40.0 mg, 0.07 mmol, 1.0 equiv, acceptor 6 (38.4 mg, 0.08 mmol, 1.2 equiv, and activated 4 Å powdered MS, was added anhyd CH2Cl2-MeCN (2:1, 3 mL, The resulted solution was stirred for 0.5 h at r.t. under Ar, and then cooled to -40°C followed by addition of NIS (37.7 mg, 0.17 mmol, 2.4 equiv) and TfOH (6.0 μL, 0.07 mmol, 1.0 equiv, The reaction was stirred at -40°C for 1 h. After quenched with Et3N 0.1 mL, the mixture was diluted with CH2Cl2, filtered through Celite, washed with 20% aq Na2S2O3 solution, dried over Na 2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography on SiO2 eluting with hexane-EtOAc system to give the coupling product
- 2 eluting with hexane-EtOAc system to give the coupling product.

34
- 62249087568
- 3): δ = 5.60 (d, J = 7.2 Hz, 1 H), 5.40 (dt, J = 6.9, 2.8 Hz, 1 H), 5.34 (d, J = 3.1 Hz, 1 H), 5.12 (m, 1 H), 4.55 (d, J = 9.4 Hz, 1 H), 4.42-4.33 (m, 2 H), 4.13 (m, 1 H), 4.01 (m, 1 H), 3.79 (s, 3 H), 3.71 (t, J = 9.8 Hz, 1 H), 3.62 (m, 1 H), 3.48-3.35 (m, 2 H), 2.90 (dd, J = 12.0, 3.2 Hz, 1 H, H-3eq), 2.49 (s, 3 H), 2.15 (s, 3 H), 2.12 (s, 3 H), 2.03 (s, 3 H), 1.01 (s, 3 H), 0.96 (d, J = 6.9 Hz, 3 H), 0.79 (s, 3 H), 0.78 (d, J = 5.7 Hz, 3 H).
- 3): δ = 5.60 (d, J = 7.2 Hz, 1 H), 5.40 (dt, J = 6.9, 2.8 Hz, 1 H), 5.34 (d, J = 3.1 Hz, 1 H), 5.12 (m, 1 H), 4.55 (d, J = 9.4 Hz, 1 H), 4.42-4.33 (m, 2 H), 4.13 (m, 1 H), 4.01 (m, 1 H), 3.79 (s, 3 H), 3.71 (t, J = 9.8 Hz, 1 H), 3.62 (m, 1 H), 3.48-3.35 (m, 2 H), 2.90 (dd, J = 12.0, 3.2 Hz, 1 H, H-3eq), 2.49 (s, 3 H), 2.15 (s, 3 H), 2.12 (s, 3 H), 2.03 (s, 3 H), 1.01 (s, 3 H), 0.96 (d, J = 6.9 Hz, 3 H), 0.79 (s, 3 H), 0.78 (d, J = 5.7 Hz, 3 H).

35
- 34250701386
- CCDC 693369 contains the supplementary crystallographic data for this paper
- CCDC 693369 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
- These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via

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