(2R,3R,4S,5S,6R)-2-[(2E)-3,7-二甲基辛-2,6-二烯氧基]-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇 合成路线 （共 9 条）
150995-11-2 (2R,3R,4S,5S,6R)-2-[(2E)-3,7-二甲基辛-2,6-二烯氧基]-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇
→
反应条件
反应条件
water T=37°C; 1.5 h; pH 6.0; hydrolysis by glucosidases II from tea leaves (cv. Yabukita); hydrolysis rate 100percent; further glucosidases and acetone powder from tea leaves;
参考文献
Guo, Wenfei; Yamauchi, Kazuyo; Watanabe, Naoharu; Usui, Taiichi; Luo, Shaojun; Sakata, Kanzo
→
反应条件
150995-11-2 (2R,3R,4S,5S,6R)-2-[(2E)-3,7-二甲基辛-2,6-二烯氧基]-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇
反应条件
sodium methylate in tetrahydrofuran; methanol
T=20°C; 0.5 h;
参考文献
Kawahara, Eiji; Fujii, Mikio; Ida, Yoshiteru; Akita, Hiroyuki
→
反应条件
150995-11-2 (2R,3R,4S,5S,6R)-2-[(2E)-3,7-二甲基辛-2,6-二烯氧基]-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇
反应条件
sodium acetate buffer; Penicillium multicolor IAM7153 β-primeverosidase in water
T=40°C; pH=5.5; 3.5 h;
参考文献
Tsuruhami, Kazutaka; Mori, Shigeharu; Sakata, Kanzo; Amarume, Satoshi; Saruwatari, Shigetaka; Murata, Takeomi; Usui, Taichi
→
反应条件
150995-11-2 (2R,3R,4S,5S,6R)-2-[(2E)-3,7-二甲基辛-2,6-二烯氧基]-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇
反应条件
1: Hg(CN)2 / acetonitrile / 3 h / Ambient temperature
2: NaOMe / methanol / 15 h / Ambient temperature
View Scheme
参考文献
Matsumura, Sachiko; Takahashi, Shunya; Nishikitani, Mariko; Kubota, Kikue; Kobayashi, Akio
→
反应条件
150995-11-2 (2R,3R,4S,5S,6R)-2-[(2E)-3,7-二甲基辛-2,6-二烯氧基]-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇
反应条件
1: Hg(CN)2 / acetonitrile / 3 h / Ambient temperature
2: 33.3 percent / TiBr4 / CH2Cl2; ethyl acetate / 1 h / Ambient temperature
3: Hg(CN)2 / acetonitrile / 3 h / Ambient temperature
4: NaOMe / methanol / 15 h / Ambient temperature
View Scheme
参考文献
Matsumura, Sachiko; Takahashi, Shunya; Nishikitani, Mariko; Kubota, Kikue; Kobayashi, Akio
→
反应条件
150995-11-2 (2R,3R,4S,5S,6R)-2-[(2E)-3,7-二甲基辛-2,6-二烯氧基]-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇
反应条件
1: Hg(CN)2 / acetonitrile / 3 h / Ambient temperature
2: NaOMe / methanol / 15 h / Ambient temperature
View Scheme
参考文献
Matsumura, Sachiko; Takahashi, Shunya; Nishikitani, Mariko; Kubota, Kikue; Kobayashi, Akio
→
反应条件
150995-11-2 (2R,3R,4S,5S,6R)-2-[(2E)-3,7-二甲基辛-2,6-二烯氧基]-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇
反应条件
1: 11 percent / immobilized β-D-glucosidase / H2O / 96 h / 50 °C
2: 63 percent / DMAP / pyridine / 24 h / 20 °C
3: 71 percent / pyridine / 12 h / 20 °C
4: 99 percent / HCl / tetrahydrofuran / 12 h / 20 °C
5: 93 percent / tetramethylurea; AgOTf / CH2Cl2 / 18 h / 20 °C
6: 71 percent / NaOMe / methanol; tetrahydrofuran / 0.5 h / 20 °C
View Scheme
参考文献
Kawahara, Eiji; Fujii, Mikio; Ida, Yoshiteru; Akita, Hiroyuki
→
反应条件
150995-11-2 (2R,3R,4S,5S,6R)-2-[(2E)-3,7-二甲基辛-2,6-二烯氧基]-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇
反应条件
1: 63 percent / DMAP / pyridine / 24 h / 20 °C
2: 71 percent / pyridine / 12 h / 20 °C
3: 99 percent / HCl / tetrahydrofuran / 12 h / 20 °C
4: 93 percent / tetramethylurea; AgOTf / CH2Cl2 / 18 h / 20 °C
5: 71 percent / NaOMe / methanol; tetrahydrofuran / 0.5 h / 20 °C
View Scheme
参考文献
Kawahara, Eiji; Fujii, Mikio; Ida, Yoshiteru; Akita, Hiroyuki
→
反应条件
150995-11-2 (2R,3R,4S,5S,6R)-2-[(2E)-3,7-二甲基辛-2,6-二烯氧基]-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇
反应条件
1: 93 percent / tetramethylurea; AgOTf / CH2Cl2 / 18 h / 20 °C
2: 71 percent / NaOMe / methanol; tetrahydrofuran / 0.5 h / 20 °C
View Scheme
参考文献
Kawahara, Eiji; Fujii, Mikio; Ida, Yoshiteru; Akita, Hiroyuki
