2,3,4,6,7-Penta-O-acetyl-L-glycero-α-D-manno-heptopyranosylbromid | 116302-67-1

• 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: 2,3,4,6,7-Penta-O-acetyl-L-glycero-α-D-manno-heptopyranosylbromid
• 英文别名: [(2S)-2-acetyloxy-2-[(2R,3S,4S,5S,6R)-3,4,5-triacetyloxy-6-bromooxan-2-yl]ethyl] acetate
• CAS: 116302-67-1
• 化学式: C₁₇H₂₃BrO₁₁
• 分子量: 483.267
• InChiKey: MRZLNGINEFTSHN-VBYGDGQVSA-N

物化性质

• 沸点：
  485.2±45.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,6,7-Penta-O-acetyl-L-glycero-α-D-manno-heptopyranosylbromid 在 palladium on activated charcoal 2,4,6-三甲基吡啶 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 25.0 ℃ 、399.99 kPa 条件下， 反应 24.0h， 生成 methyl O-(α-D-glucopyransoyl)-(1->3)-O-<α-L-glycero-D-manno-heptopyranosyl-(1->7)>-L-glycero-α-D-manno-heptopyranoside
  参考文献：
  名称：

  Synthesis of methyl 3-O-(α-d-glucopyranosyl)-7-O-(l-glycero-α-d-manno-heptopyranosyl)-l-glycero-α-d-manno- heptopyranoside

  摘要：

  The title trisaccharide glycoside, which is related to part of the core region of the lipopolysaccharide from Salmonella, and the disaccharide glycosides methyl 3-O-alpha-D-glucopyranosyl-L-glycero-alpha-D-manno-heptopyranoside and methyl 7-O-L-glycero-alpha-D-manno-heptopyranosyl-L-glycero-alpha-D-manno- heptopyranoside have been synthesised. Methyl 2,3,4-tri-O-benzyl-L-glycero-alpha-D-manno- heptopyranoside, obtained via a one-carbon elongation at C-6 of methyl 2,3,4-tri-O-benzyl-alpha-D-manno- hexodialdo-1,5-pyranoside, was used as precursor both for the heptosyl donor and acceptor.

  DOI：

  10.1016/0008-6215(90)80133-n
• 作为产物：
  描述：

  L-glycero-D-manno-heptopyranose hexa-acetate 在 溴化钛(IV) 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 72.0h， 以73%的产率得到2,3,4,6,7-Penta-O-acetyl-L-glycero-α-D-manno-heptopyranosylbromid
  参考文献：
  名称：

  Paulsen, Hans; Heitmann, Axel C., Liebigs Annalen der Chemie, 1988, p. 1061 - 1072

  摘要：

  DOI：

文献信息

• Novel Synthesis of Disaccharides Containing the 2-Amino-2-deoxy-β-D-glucopyranosyl Unit and L-<i>Glycero</i>-D-<i>Manno</i>- and 7-Deoxy-L-<i>Glycero</i>-D-<i>Galacto</i>-heptopyranoses
  作者：Patrick Martin、Vincent Lequart、Roméo Cecchelli、Paul Boullanger、Dominique Lafont、Joseph Banoub

  DOI：10.1246/cl.2004.696

  日期：2004.6

  Stereocontrolled syntheses of immunologically relevant heptopyranose disaccharides were achieved in excellent yields by the trimethylsilyl triflate promoted glycosylation of the donor 1,3,4,6-tetra-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-β-d-glucopyranose with the adequate acceptors.

  通过三甲基硅基三氟甲磺酸盐促进的供体1,3,4,6-四-O-乙酰基-2-N-烯丙氧基羰基-2-氨基-2-脱氧-β-D-吡喃葡萄糖与适当受体的糖基化反应，实现了免疫相关七吡喃糖二糖的立体控制合成，且收率极高。
• Paulsen, Hans; Wulff, Achim; Brenken, Mathias, Liebigs Annalen der Chemie, 1991, # 11, p. 1127 - 1146
  作者：Paulsen, Hans、Wulff, Achim、Brenken, Mathias

  DOI：——

  日期：——
• Synthesis of ld-Hepp and KDO containing di- and tetrasaccharide derivatives of Neisseria meningitidis inner-core region via iodonium ion promoted glycosidations
  作者：G.J.P.H. Boons、F.L. van Delft、P.A.M. van der Klein、G.A. van der Marel、J.H. van Boom

  DOI：10.1016/s0040-4020(01)88191-6

  日期：——

  The synthesis of methyl(ethyl) 2-thio-KDO (i.e. 1, 2, 5, 7 and 10) and ethyl 1-thio-LD-Hepp (i.e. 26 and 43) derivatives will be described. The latter derivatives proved to be suitable donors in iodonium ion (NIS/IFOH) promoted glycosidation reactions. The usefulness of the glycosidation approach was illustrated by the successful conclusion of a spacer containing dimer L-alpha-D-Hepp-(1 --> 5)-alpha-KDO-2-O-(CH2)3NH2 (37) and tetramer beta-D-Galp-(1 --> 4)-beta-D-Glep-(1 --> 4)-L-alpha-D-Hepp-(1 -->5)-alpha-KDO-2-O-(CH2)3NH2 (47).
• Boons, G. J. P. H.; Marel, G. A. van der; Poolman, J. T., Recueil des Travaux Chimiques des Pays-Bas, 1989, vol. 108, # 10, p. 339 - 343
  作者：Boons, G. J. P. H.、Marel, G. A. van der、Poolman, J. T.、Boom, J. H. van

  DOI：——

  日期：——
• Synthesis of a trisaccharide of the inner core region of Citrobacter PCM 187 lipopolysaccharide that contains l-glycero-α-d-manno-heptopyranosyl units
  作者：Geert J.P.H. Boons、Marc Overhand、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/0008-6215(89)85198-5

  日期：1989.10