- Efficient total syntheses of natural pterin glycosides: limipterin and tepidopterin
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The key, versatile precursors N2-(N,N-dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (29a) and its ciliapterin analog (29b) were prepared, respectively, from d-xylose (in 14 steps) and l-xylose (in 11 steps). Treatment of 29a and 29b with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups, led to the first selective syntheses of limipterin (3) and tepidopterin (5), respectively.
- Hanaya, Tadashi,Baba, Hiroki,Toyota, Hiroki,Yamamoto, Hiroshi
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p. 2090 - 2100
(2008/09/18)
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- Novel preparation of a 2′-O-acetyl-1′-O-(4-methoxybenzyl)-L- biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides
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L-Rhamnose was converted, over a 13-step-sequence, into 2′-O-acetyl-N2-(N,N-dimethylaminomethylene)-1′-O-(4- methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-L-biopterin, an appropriately protected precursor of 1′-O- and 2′-O-monoglycosyl-L-biopterin.
- Hanaya, Tadashi,Toyota, Hiroki,Yamamoto, Hiroshi
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p. 2075 - 2078
(2008/02/05)
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- An efficient synthesis of 2′-O-(β-d-glucopyranosyl)- and 2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-biopterins
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N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1′,2′-di-O-trimethylsilyl-L-biopterin (6) was prepared from L-biopterin in 5 steps. Glycosylation of 6 with 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate (9) and 1,3,4
- Hanaya, Tadashi,Soranaka, Kazuyuki,Harada, Koichiro,Yamaguchi, Hiroshi,Suzuki, Ryo,Endo, Yusumi,Yamamoto, Hiroshi,Pfleiderer, Wolfgang
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p. 299 - 310
(2007/10/03)
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