methyl 2,3,4-tri-O-(trimethylsilyl)-α-D-mannopyranoside | 146399-85-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-(trimethylsilyl)-α-D-mannopyranoside
• 英文别名: methyl 2,3,4-tri-O-trimethylsilyl-α-D-mannopyranoside；[(2R,3R,4S,5S,6S)-6-methoxy-3,4,5-tris(trimethylsilyloxy)oxan-2-yl]methanol
• CAS: 146399-85-1
• 化学式: C₁₆H₃₈O₆Si₃
• 分子量: 410.731
• InChiKey: VFMWHUHHZDIWSF-OWYFMNJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-(trimethylsilyl)-α-D-mannopyranoside 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3R,4S,5S,6S)-6-Methoxy-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-carbaldehyde
  参考文献：
  名称：

  Synthesis and biological evaluation of new mannose 6-phosphate analogues

  摘要：

  Three new analogues of mannose 6-phosphate (M6P)-a sulphate and two carboxylates-have been synthesized and their affinity toward the M6P/IGFII receptor evaluated by affinity column chromatography. These compounds display strong binding to the receptor and therefore are new M6P analogues which may find some dermatological applications. for example healing of post-surgical scars. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00264-x
• 作为产物：
  描述：

  甲基-D-丙噻 在 吡啶 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 methyl 2,3,4-tri-O-(trimethylsilyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Large-scale synthesis of d-mannose 6-phosphate and other hexose 6-phosphates

  摘要：

  The syntheses of D-mannose 6-phosphate (4), several D-mannopyranoside 6-phosphates, and methyl alpha-D-glucopyranoside 6-phosphate are described. Phosphorylation of methyl 2,3,4-tri-O-(trimethylsilyl)-alpha-D-mannopyranoside (2) with phosphorus oxychloride followed by careful hydrolysis gave methyl alpha-D-mannopyranoside 6-phosphate (10, 81%). Direct phosphorylation of 1,2,3,4,6-penta-O-(trimethylsiyl)-alpha-D-mannopyranoside with phosphorus oxychloride followed by hydrolysis gave 4 (50% yield based on D-mannose). The first method was further used in the synthesis of methyl, butyl, and hexadecyl alpha-D-mannopyranoside 6-phosphate disodium salts, and in the synthesis of methyl alpha-D-glucopyranoside 6-phosphate disodium salt.Compound 2 was obtained in 67% yield, from methyl 2,3,4,6-tetra-O-(trimethylsilyl)-alpha-D-mannopyranoside, by selective hydrolysis with a saturated solution of potassium carbonate in methanol.Butyl and hexadecyl alpha-D-mannopyranosides were prepared by glycosidation of the respective alcohols with tetra-O-benzoyl-alpha-D-mannopyranosyl bromide in silver triflate-promoted reactions.

  DOI：

  10.1016/0008-6215(92)80082-c

文献信息

• Synthesis of the Dipotassium Salts of Methyl α-D-Mannopyranoside 6-Phosphorothioate and D-Mannose 6-Phosphorothioate
  作者：Alan H. Haines、D. James R. Massy

  DOI：10.1055/s-1996-4421

  日期：1996.12

  Dipotassium methyl α-D-mannopyranoside 6-phosphorothioate (4) and dipotassium D-mannose 6-phosphorothioate (7) have been prepared from per-O-trimethylsilyl derivatives of methyl α-D-mannopyranoside and D-mannopyranose, respectively, through reaction sequences involving selective cleavage in the pyranoside ether, and selective replacement in the pyranose ether, of a 6-O-trimethylsilyl group.

  δ-D-吡喃甘露糖苷 6-硫代磷酸二钾盐（4）和 D-甘露糖苷 6-硫代磷酸二钾盐（7）分别由δ-D-吡喃甘露糖苷甲基和 D-吡喃甘露糖的过-O-三甲基硅基衍生物通过选择性裂解吡喃糖苷醚和选择性置换吡喃糖醚中的 6-O-三甲基硅基的反应序列制备而成。
• Large-scale synthesis of d-mannose 6-phosphate and other hexose 6-phosphates
  作者：Morten Meldal、Mette Knak Christensen、Klaus Bock

  DOI：10.1016/0008-6215(92)80082-c

  日期：1992.11

  The syntheses of D-mannose 6-phosphate (4), several D-mannopyranoside 6-phosphates, and methyl alpha-D-glucopyranoside 6-phosphate are described. Phosphorylation of methyl 2,3,4-tri-O-(trimethylsilyl)-alpha-D-mannopyranoside (2) with phosphorus oxychloride followed by careful hydrolysis gave methyl alpha-D-mannopyranoside 6-phosphate (10, 81%). Direct phosphorylation of 1,2,3,4,6-penta-O-(trimethylsiyl)-alpha-D-mannopyranoside with phosphorus oxychloride followed by hydrolysis gave 4 (50% yield based on D-mannose). The first method was further used in the synthesis of methyl, butyl, and hexadecyl alpha-D-mannopyranoside 6-phosphate disodium salts, and in the synthesis of methyl alpha-D-glucopyranoside 6-phosphate disodium salt.Compound 2 was obtained in 67% yield, from methyl 2,3,4,6-tetra-O-(trimethylsilyl)-alpha-D-mannopyranoside, by selective hydrolysis with a saturated solution of potassium carbonate in methanol.Butyl and hexadecyl alpha-D-mannopyranosides were prepared by glycosidation of the respective alcohols with tetra-O-benzoyl-alpha-D-mannopyranosyl bromide in silver triflate-promoted reactions.
• Synthesis and biological evaluation of new mannose 6-phosphate analogues
  作者：Sébastien Vidal、Marcel Garcia、Jean-Louis Montero、Alain Morère

  DOI：10.1016/s0968-0896(02)00264-x

  日期：2002.12

  Three new analogues of mannose 6-phosphate (M6P)-a sulphate and two carboxylates-have been synthesized and their affinity toward the M6P/IGFII receptor evaluated by affinity column chromatography. These compounds display strong binding to the receptor and therefore are new M6P analogues which may find some dermatological applications. for example healing of post-surgical scars. (C) 2002 Elsevier Science Ltd. All rights reserved.