TY - JOUR
T1 - Synthesis of 2,4-dideoxy-4-hydroxyphosphonoyl-D-erythro- and -L-threo-pentofuranoses
AU - Hanaya, Tadashi
AU - Noguchi, Ayashi
AU - Armour, Margaret Ann
AU - Hogg, Alan M.
AU - Yamamoto, Hiroshi
PY - 1992/1/1
Y1 - 1992/1/1
N2 - Treatment of 3,5, 6-trideoxy-1,2-O-isopropylidene-6-nitro-α-D- erythro-hex-5-enofuranose with dimethyl phosphonate in the presence of triethylamine, followed by catalytic hydrogenation and then deamination with nitrous acid, provided mainly a 2:1 mixture of 3,5-dideoxy-5- dimethoxyphosphinoyl-1,2-O-isopropylidene-α-D-ribo- and -β-L-lyxo-hexofuranose in 57% overall yield. This mixture was deacetonated, oxidized with sodium periodate, and then treated with acidic methanol to afford methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-α,β-D-erythro- pentopyranosides (41% over-all yield from the aforementioned phosphinoylfuranose) and -L-threo-pentopyranosides (17% overall yield). The major products were reduced with sodium dihydrobis-(2-methoxyethoxy)-aluminate, followed by hydrolysis with acid and then oxidation with hydrogen peroxide, to afford the title D-erythro compounds, whereas similar treatment of the minor pyranosides afforded the corresponding L-threo-pentofuranoses. These compounds were converted into the corresponding 1,3,5-tri-O-acetyl-5-methoxyphosphonoyl derivatives, whose structures and conformations [mostly 3T 2(D) for one and 2T3(L) for the other] were established by spectroscopy.
AB - Treatment of 3,5, 6-trideoxy-1,2-O-isopropylidene-6-nitro-α-D- erythro-hex-5-enofuranose with dimethyl phosphonate in the presence of triethylamine, followed by catalytic hydrogenation and then deamination with nitrous acid, provided mainly a 2:1 mixture of 3,5-dideoxy-5- dimethoxyphosphinoyl-1,2-O-isopropylidene-α-D-ribo- and -β-L-lyxo-hexofuranose in 57% overall yield. This mixture was deacetonated, oxidized with sodium periodate, and then treated with acidic methanol to afford methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-α,β-D-erythro- pentopyranosides (41% over-all yield from the aforementioned phosphinoylfuranose) and -L-threo-pentopyranosides (17% overall yield). The major products were reduced with sodium dihydrobis-(2-methoxyethoxy)-aluminate, followed by hydrolysis with acid and then oxidation with hydrogen peroxide, to afford the title D-erythro compounds, whereas similar treatment of the minor pyranosides afforded the corresponding L-threo-pentofuranoses. These compounds were converted into the corresponding 1,3,5-tri-O-acetyl-5-methoxyphosphonoyl derivatives, whose structures and conformations [mostly 3T 2(D) for one and 2T3(L) for the other] were established by spectroscopy.
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U2 - 10.1039/p19920000295
DO - 10.1039/p19920000295
M3 - Article
AN - SCOPUS:37049083165
SP - 295
EP - 301
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
SN - 1472-7781
IS - 2
ER -