(2S,3S,4R,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-yl acetate | 948036-06-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-yl acetate
• 英文别名: allyl 3-O-acetyl-2,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-α-D-altropyranoside；Bn(-2)[Bn(-4)][TBDMS(-6)]D-Alt3Ac(a)-O-allyl；[(2R,3R,4R,5S,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,5-bis(phenylmethoxy)-6-prop-2-enoxyoxan-4-yl] acetate
• CAS: 948036-06-4
• 化学式: C₃₁H₄₄O₇Si
• 分子量: 556.772
• InChiKey: ORUNGWAECQCZOT-LBEKWILNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-yl acetate 在 palladium dichloride calcium sulfate 、 cerium(III) chloride 、 三氟甲磺酸 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 acetate buffer 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 7.0h， 生成 (1R,2R,3R,4S,5R)-2,3,4-tris(benzyloxy)-5-vinyl-6,8-dioxabicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthesis of a partially benzylated derivative of the anhydro-d-altro-heptulose found in Coriaria japonica A

  摘要：

  A partially benzylated derivative of the anhydro-D-altro-heptulose found in Coriaria japonica A, which is a synthetically useful unit, was successfully synthesized from a D-mannose derivative by a novel synthetic approach involving an intramolecular O-ketopyranosylation. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.057
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 吡啶 、 咪唑 、 18-冠醚-6 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 28.5h， 生成 (2S,3S,4R,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-yl acetate
  参考文献：
  名称：

  Synthesis of a partially benzylated derivative of the anhydro-d-altro-heptulose found in Coriaria japonica A

  摘要：

  A partially benzylated derivative of the anhydro-D-altro-heptulose found in Coriaria japonica A, which is a synthetically useful unit, was successfully synthesized from a D-mannose derivative by a novel synthetic approach involving an intramolecular O-ketopyranosylation. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.057

文献信息

• Syntheses of a partially benzylated derivative of the anhydro-d-altro-heptulose found in Coriaria japonica A and of its analogs
  作者：Sho Matsuda、Takashi Yamanoi、Mikio Watanabe

  DOI：10.1016/j.tet.2008.06.068

  日期：2008.8

  A partially benzylated derivative of anhydro-D-altro-heptulose found in Coriaria japonica A, which is a synthetically useful unit, was successfully synthesized from a D-mannose derivative by a novel synthetic approach involving the intramolecular O-ketopyranosylation reaction developed by us. This synthetic approach was also applicable to the preparation of its four analogs. (C) 2008 Elsevier Ltd. All rights reserved.