3-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-1-propene | 145987-58-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-1-propene
• 英文别名: [(2S,3R,4R,5R,6R)-4,5-diacetyloxy-2-methyl-6-prop-2-enyloxan-3-yl] acetate
• CAS: 145987-58-2
• 化学式: C₁₅H₂₂O₇
• 分子量: 314.335
• InChiKey: PRUAJEBYYJKUEH-LMYWXWJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-1-propene 在 platinum(IV) oxide 吡啶 、 sodium tetrahydroborate 、 氢气 、 臭氧 作用下， 以 甲醇 为溶剂， 反应 50.0h， 生成 Acetic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-6-methyl-2-(2-phosphonooxy-ethyl)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of C-fucopyranosyl analogs of GDP-L-fucose as inhibitors of fucosyltransferases

  摘要：

  The syntheses of the C-fucopyranosyl analogs of GDP-L-fucose 2 - 5 as potential inhibitors of fucosyltransferases are reported. The synthetic routes are based on the C-glycosidation of tetra-O-acetyl-alpha-L-fucopyranose 6 under conditions that provided either beta- or alpha- C-fucosides with high stereoselectivity. Coupling to GMP was effected by Khorana's phosphomorpholidate method.

  DOI：

  10.1016/s0040-4039(00)60893-6
• 作为产物：
  描述：

  2',3',4'-tri-O-acetyl-α,β-L-fucopyranosyloxy-1,3,2-dioxaphosphinane 2-oxide 、 烯丙基三甲基硅烷 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到3,4,5-tri-O-acetyl-2,6-anhydro-1,7,8,9-tetradeoxy-L-glycero-D-galacto-non-8-enitol
  参考文献：
  名称：

  Efficient stereocontrolled synthesis of C-glycosides using glycosyl donors substituted by propane 1,3-diyl phosphate as the leaving group

  摘要：

  a- and beta -Glycosyl cyanides, per-O-acetyl-1,2-O-1-cyanoethylidenes and C-allyl glycopyranosides were efficiently prepared by treatment of 2,3,4-tri-O-acetyl-alpha,beta -L-rhamno-, L-fuco- and 2,3,4,6-tetra-O-acetyl-alpha,beta -D-galactopyranosyl propane-1,3-diyl phosphates with trimethylsilyl cyanide (TMSCN) and allyltrimethylsilane in the presence of trimethylsilyl triflate (TMSOTf). Similarly 2,3,4,6-tetra-O-benzyl-alpha,beta -D-manno- and D-glucopyranosyl propane-1,3-diyl phosphates were employed in the synthesis of C-glycosides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00305-6