SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 13, 2008, Pages 1969-1972

Fast and efficient preparation of an α-fucosyl building block by reductive 1,2-benzylidene ring-opening reaction

(3) Werz, Daniel B a Schuster, Heiko J a Tietze, Lutz F a

a UNIVERSITY OF GÖTTINGEN (Germany)

Author keywords

Benzylidene; Building block; Carbohydrates; Fucose; Protecting group

Indexed keywords

1,2 BENZYLIDENE; ALPHA FUCOSYL; BENZYLIDENE DERIVATIVE; FUCOSE; LEWIS ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 49649129726 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1077961 Document Type: Article

Times cited : (5)

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- 4-Di-0-benzoyl-1,2-0-benzylidene-a-L- fucopyranose (6) To a stirred solution of fucosyl bromide 5 (16.9 g, 31.3 mmol, 1.00 equiv) in abs. MeCN (106 mL) was added dry KI (7.46 g, 44.9 mmol, 1.43 equiv) and NaBH4 (1.13 g, 29.9 mmol, 0.96 equiv, The mixture was stirred for 2.5 h. Then more NaBH4 (1.13g, 29.9 mmol, 0.96 equiv) was added. After a total reaction time of 5 h, the solvent was removed. The residue was dissolved in EtOAc, washed with ice water, cold sat. NaHCO3 solution, and twice with brine. The mixture was dried (Na 2SO4, concentrated, and the residue purified by column chromatography (SiO2; pentane-EtOAc, 5:1) to afford 10.2 g (71, of 6 as a colorless foam. Analytical Data of the exo-Product IR (KBr, 2985,1727,1602,1452,1280cm-1. 1HNMR(SOO MHz, CDCl3, δ, 1.31 (d, J= 6.2 Hz, 3 H, 4.51 dd
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38
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- 4-Di-O-benzoyl-2-0-benzyl-α/ β-L-fucopyranose (7) To a stirred solution of benzylidene fucose 6(161 mg, 0.35 mmol, 1.0 equiv) in abs. THF (2 mL) BH3-THF (0.53 mL, 0.53 mmol, 1.5 equiv) was added at r.t, then Bu2BOTf (52 μL, 0.053 mmol, 0.15 equiv, The mixture was stirred for 1-2 h. Water was added and the reaction mixture was extracted with EtOAc. The organic phase was dried (Na 2SO4, concentrated, and the residue purified by column chromatography (SiO2; pentane-EtOAc, 3:1 to 2:1, to afford 72 mg (45, of 7 and 70 mg (43, of 8 as a colorless foam. The two products were easily separable (7 is much more polar than 8, Analytical Data of the Anomeric Mixture (1:1) of 7 IR (film, 3434, 2936, 1726, 1602, 1453, 1283 cm-1. 1H NMR (300 MHz, CDCl3, δ, 1.19 (d, J= 6.1 Hz, 3 H, 1.27 (d, J= 6.1 Hz, 3 H, 3.38 br s, 1
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40
- 49649128020
- Analytical Data of the a-Anomer [α]D20 -148.4 (c 1.90, CDCl3, IR (film, 2943, 2867, 1733, 1672, 1464, 1278 cm-1. 1H NMR (300 MHz, CDCl3, δ, 1.24 (d, J= 6.1 Hz, 3 H, 4.29 (dd, J= 7.8, 3.4 Hz, 1 H, 4.55 (m, 1 H, 4.61 (d, J= 7.8 Hz, 1 H, 4.69 (d, J= 7.8 Hz, 1 H, 4.75-5.81 (m, 2 H, 6.68 (d, J= 3.4 Hz, 1 H, 7.23-7.33 (m, 7 H, 7.43-7.49 (m, 3 H, 7.62 (m, 1 H, 7.80 (m, 2 H, 7.94 (m, 2 H, 8.66 (s, 1 H, 13C NMR 75 MHz, CDCl3, δ, 16.2, 67.8, 70.3, 71.7, 72.3, 72.6, 91.2, 94.5, 127.8, 127.9, 127.9, 128.0, 128.2, 128.3, 128.5, 129.4, 129.5, 129.6, 129.7, 133.0, 133.3, 137.4, 161.4, 165.5, 165.7. ESI-HRMS: m/z calcd for C29H26Cl3NO7Na: 628.06725; found: 628.06734
- 7Na: 628.06725; found: 628.06734.

41
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