2',3',4'-tri-O-acetyl-α-L-fucopyranosyloxy-1,3,2-dioxaphosphinane 2-oxide | 225217-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',3',4'-tri-O-acetyl-α-L-fucopyranosyloxy-1,3,2-dioxaphosphinane 2-oxide
• 英文别名: propane-1,3-diyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl phosphate；[(2S,3R,4R,5S,6S)-4,5-diacetyloxy-2-methyl-6-[(2-oxo-1,3,2lambda5-dioxaphosphinan-2-yl)oxy]oxan-3-yl] acetate；[(2S,3R,4R,5S,6S)-4,5-diacetyloxy-2-methyl-6-[(2-oxo-1,3,2λ5-dioxaphosphinan-2-yl)oxy]oxan-3-yl] acetate
• CAS: 225217-38-9
• 化学式: C₁₅H₂₃O₁₁P
• 分子量: 410.315
• InChiKey: KQNVIGVGQHYABI-KVOGPGQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2',3',4'-tri-O-acetyl-α-L-fucopyranosyloxy-1,3,2-dioxaphosphinane 2-oxide 、 1,3,4,6-四-o-乙酰基-alpha-d-吡喃半乳糖 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以46%的产率得到hepta-O-acetyl-2-O-β-L-fucopyranosyl-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis of fucosidase substrates using propane-1,3-diyl phosphate as the anomeric leaving group

  摘要：

  Activation of the anomeric centre of suitably protected L-fucopyranose and D-galactopyranose with propane-1,3-diyl phosphate allowed the synthesis of the disaccharide alpha-L-Fucp-(1,2)-beta-D-Galp(1)-4-methylumbelliferone as a fucosidase substrate. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00571-7
• 作为产物：
  描述：

  6-deoxy-L-galactose 在 N-甲基咪唑 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 28.25h， 生成 2',3',4'-tri-O-acetyl-α-L-fucopyranosyloxy-1,3,2-dioxaphosphinane 2-oxide
  参考文献：
  名称：

  Synthesis of fucosidase substrates using propane-1,3-diyl phosphate as the anomeric leaving group

  摘要：

  Activation of the anomeric centre of suitably protected L-fucopyranose and D-galactopyranose with propane-1,3-diyl phosphate allowed the synthesis of the disaccharide alpha-L-Fucp-(1,2)-beta-D-Galp(1)-4-methylumbelliferone as a fucosidase substrate. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00571-7

文献信息

• Stereoselective synthesis of α-L-Fucp-(1,2)- and -(1,3)-β-D-Galp(1)-4-methylumbelliferone using glycosyl donor substituted by propane-1,3-diyl phosphate as leaving group
  作者：Hariprasad Vankayalapati、Gurdial Singh

  DOI：10.1039/b002754p

  日期：——

  The synthesis of the disaccharides α-L-Fucp-(1,2)- and α-L-Fucp-(1,3)-β-D-Galp(1)-4-methylumbelliferone as fucosidase substrates was accomplished by activation of the anomeric centre of 2,3,4-tri-O-acetyl- and 2,3,4,6-tetra-O-acetyl-α,β-L-fuco- and -D-galactopyranosyl propane-1,3-diyl phosphates with TMSOTf and with minimal protection of 4-methylumbelliferyl β-D-galactopyranoside.

  合成双糖α-L-岩藻糖-(1,2)-和α-L-岩藻糖-(1,3)-β-D-半乳糖-(1)-4-甲基伞花素作为岩藻糖苷酶底物，通过用TMSOTf激活2,3,4-三-O-乙酰基和2,3,4,6-四-O-乙酰基α,β-L-岩藻糖和-D-半乳糖基丙烷-1,3-二醇磷酸盐的异头中心，并对4-甲基伞花素β-D-半乳糖苷进行了最小保护。