Synlett 2012; 23(13): 1919-1922
DOI: 10.1055/s-0032-1316685
letter
© Georg Thieme Verlag Stuttgart · New York

A Three-Component, One-Pot, Sequential Synthesis of a Common Tetrasaccharide Block Related to the Lipopolysaccharide of the Escherichia Coli O9, Klebsiella pneumonia O3, and Hafnia alvei PCM 1223

Sajal Kumar Maity
Department of Chemistry, Jadavpur University, Kolkata 700 032, India, Fax: +91(33)24146266   Email: ghoshrina@yahoo.com   Email: ghosh_rina@hotmail.com
,
Rina Ghosh*
Department of Chemistry, Jadavpur University, Kolkata 700 032, India, Fax: +91(33)24146266   Email: ghoshrina@yahoo.com   Email: ghosh_rina@hotmail.com
› Author Affiliations
Further Information

Publication History

Received: 13 April 2012

Accepted after revision: 10 June 2012

Publication Date:
23 July 2012 (online)


Abstract

An expeditious three-component, one-pot, sequential synthesis of a common block tetrasaccharide fragment Manp-(1→3)-Manp-(1→2)-Manp-(1→2)-Manp related to the pentasaccharide repeating unit of the O-antigen of Escherichia Coli O9, Klebsiella pneumonia O3, and Hafnia alvei PCM 1223 with minimal protecting group manipulation is reported.

Supporting Information

 
  • References and Notes

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  • 18 One-Pot Procedure for the Preparation of Methyl (2-O-Acetyl-3,4,6-tri-O-benzyl-α-d-mannopyranosyl)-(1→3)-(2-O-acetyl-4,6-O-benzylidene-α-d-mannopyranosyl)-(1→2)-(3,4,6-tri-O-benzyl-α-d-mannopyranosyl)-(1→2)-3,4,6-tri-O-benzyl-α-d-mannopyranoside (2): A solution of 3 (58.2 mg, 0.0997 mmol), 4 (40.1 mg, 0.0997 mmol), NMPTC (25.9 mg, 0.1097 mmol), and flame-activated 4 Å MS were stirred in anhydrous CH2Cl2 (4 mL) for 0.5 h at room temperature. The reaction mixture was then cooled to –45 °C and stirred for 5 min before TMSOTf (20 μL, 0.1105 mmol) was injected. The temperature was then increased gradually to –10 °C and stirred for 20 min. After the donor 3 was consumed, the reaction temperature lowered to –45 °C and disaccharide acceptor 5 (107.1 mg, 0.1195 mmol) was added. Subsequently, a second portion of NMPTC (28.6 mg, 0.1212 mmol) and TMSOTf (22 μL, 0.1218 mmol) were added. The temperature was then increased gradually from –45 to –10 °C in 0.5 h and the reaction mixture was stirred at –10 °C for an additional 0.5 h. The reaction was quenched with Et3N (1 mL). The reaction mixture, after dilution with CH2Cl2 (10 mL), was filtered through a plug of Celite, and the bed was washed with CH2Cl2 (3 × 10 mL). The combined filtrate and washings was concentrated under reduced pressure and the crude mixture was directly purified by silica gel flash column chromatography (hexane–EtOAc, 4:1) to afford 2 (89.4 mg, 54%) as a glassy syrup. Rf = 0.25 (EtOAc–hexane, 20%); [α]D 26 +25.3 (c 0.94, CHCl3); 1H NMR (300 MHz, CDCl3): δ = 7.37–7.17 (m, 50 H, ArH), 5.62 (s, 1 H, PhCH), 5.52 (dd, J = 5.2, 1.8 Hz, 1 H, H-2′′′), 5.41 (dd, J = 3.5, 1.3 Hz, 1 H, H-2′′), 5.29 (d, J = 1.4 Hz, 1 H, H-1′′′), 5.18 (d, J = 1.2 Hz, 1 H, H-1′), 5.01 (d, J = 1.2 Hz, 1 H, H-1′′), 4.87–4.82 (m, 3 H, H-1, PhCH2 ), 4.73–4.51 (m, 13 H), 4.48 (d, J = 4.5 Hz, 1 H), 4.40 (dd, J = 9.4, 3.6 Hz, 1 H, H-3′′), 4.30 (d, J = 12.2 Hz, 1 H, PhCH2), 4.17 (dd, J = 10.0, 3.6 Hz, 1 H, H-6′′), 4.10 (t, J = 2.4 Hz, 1 H, H-2′), 4.06–3.70 (m, 19 H, H-3, H-4, H-5, H-6, H-3′, H-4′, H-5′, H-6a′, H-6b′, H-4′′, H-5′′, H-6′′, H-3′′′, H-4′′′, H-5′′′, H-6a′′′, and H-6b′′′), 3.57 (dd, J = 10.5, 1.5 Hz, 1 H, H-6), 3.22 (s, 3 H, OCH3), 2.10 (s, 3 H, COCH3), 2.09 (s, 3 H, COCH3); 13C NMR (75 MHz, CDCl3): δ = 170.3 (C=O), 169.7 (C=O), 138.7, 138.6, 138.43, 138.34, 138.28, 138.24, 138.1, 137.1, 128.7, 128.4, 128.33, 128.27, 128.2, 128.0, 127.94, 127.88, 127.8, 127.7, 127.63, 127.61, 127.56, 127.52, 127.49, 127.43, 127.39, 126.0, 101.3 (PhCH), 100.6 (C-1′, 1 J C––H = 171.6 Hz), 99.9 (C-1′′, 1 J C–H = 170.8 Hz), 99.7 (C-1, 1 J C–H = 170.4 Hz), 98.9 (C-1′′′, 1 J C–H = 178.0 Hz), 79.3, 78.9, 77.7, 77.2, 75.4, 75.2, 75.1, 75.0, 74.9, 74.0, 73.32, 73.27, 72.2, 72.1, 71.7, 71.67, 71.5, 70.9, 69.4, 69.3, 68.6, 68.4, 68.3, 64.1, 54.6, 21.0, 20.9; HRMS (ESI-TOF): m/z [M + Na]+ calcd for C99H106O23Na: 1685.7023; found: 1685.7030.