(E,2R,3S,4R)-6-methoxy-1,3,4-tris(phenylmethoxy)hex-5-en-2-ol | 127940-33-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E,2R,3S,4R)-6-methoxy-1,3,4-tris(phenylmethoxy)hex-5-en-2-ol
• CAS: 127940-33-4
• 化学式: C₂₈H₃₂O₅
• 分子量: 448.559
• InChiKey: LSXYCYLNJMYRGF-SGNYUJCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E,2R,3S,4R)-6-methoxy-1,3,4-tris(phenylmethoxy)hex-5-en-2-ol 在 重铬酸吡啶 、 盐酸羟胺 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  邻基参与形成腈的贝克曼断裂反应：对映体纯 (E)-2,3-二-O-取代-5-甲氧基-戊-4-烯腈的合成及其转化为吡喃糖胺

  摘要：

  多功能酮肟的选择性贝克曼碎裂已被证明可以有效地进行，以产生相应的腈。手性 (E)-1,3,4-三-O-取代-6-甲氧基-hex-5-en-2-one 肟衍生物，可从糖基和糖基糖基中获得，得到对映体纯 (E)-2,3 -二-O-取代的-5-甲氧基戊-4-烯腈通过用甲磺酰氯和三乙胺处理。C1-C2 异裂裂解完全由相邻的 C1 醚氧控制和引导，产生碳正离子作为活性电离基团。出乎意料的是，C3 杂原子并没有帮助裂解反应，并且从未检测到来自 C2-C3 碎片的产物。讨论了基于立体化学结果的断裂反应的出色区域和立体特异性。还描述了一些吡喃糖胺的简单合成方法。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200400498
• 作为产物：
  描述：

  3,4,6-三邻苄基半乳醛 在 sodium tetrahydroborate 、 thallium(III) nitrate 作用下， 以 甲醇 为溶剂， 生成 (Z)-(2R,3S,4R)-1,3,4-Tris-benzyloxy-6-methoxy-hex-5-en-2-ol 、 (E,2R,3S,4R)-6-methoxy-1,3,4-tris(phenylmethoxy)hex-5-en-2-ol
  参考文献：
  名称：

  A new entry into versatile ring opening of O-benzyl glycals and related compounds via Tl(NO3)3 and NaBH4

  摘要：

  DOI：

  10.1016/s0040-4039(01)93784-0

文献信息

• Stereoselective synthesis of tetrahydrofurans and linear methyl enol-ethers from glycals
  作者：Enzo Bettelli、Piero D'Andrea、Stefano Mascanzoni、Pietro Passacantilli、Giovanni Piancatelli

  DOI：10.1016/s0008-6215(97)10062-3

  日期：1998.1

  The O-benzyl derivatives of 1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (D-glucal, 1), 1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol (L-rhamnal, 7), and I,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol (D-galactal, 9), underwent stereoselectively a ring contraction by treatment with thallium(II:I) nitrate (TTN) in MeOH, giving respectively the dimethylacetal derivatives of 3,4,6-tri-O-benzyl-2,5-anhydro-D-mannose, 3,4-di-O-benzyl-6-deoxy-2,5-anhydro-L-mannose (8) and 3,4,6-tri-O-benzyl-2,5-anhydro-D-talose (10).Conversely, the protected glycals 1, 7 and 9, underwent the ring opening reaction by action of the TTN-NaBH4, reagent in MeOH, providing the enantiomerically pure methyl enol-ethers 3,4,6-tri-O-benzyl-2-deoxy-1-O-methyl-D-arabino-hex-1-enitol, 3,4-di-O-benzyl-2,6-dideoxy-1-O-methyl-L-arabino-hex-1-enitol and 3,4,6-tri-O-benzyl-2-deoxy-1-O-methyl-D-lyxo-hex-1-enitol. The perbenzylated glycosyl-glycals, such as 3,4-di-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (cellobial) (16), 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-beta-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (lactal) (19) and 3,4-di-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (melibial) (22), showed the same reactivity as the corresponding glycals by reaction with TTN in MeOH, resulting selectively in the ring contracted compounds at the glycal moiety. The reaction with TTN-NaBH4, in MeOH, carried out on 16, 19 and 22, led to the formation of the open chain derivatives at the glycal site. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Mercuration-reductive demercuration of glycals: A mild and convenient entry to 2-deoxy-sugars
  作者：Enzo Bettelli、Paola Cherubini、Piero D'Andrea、Pietro Passacantilli、Giovanni Piancatelli

  DOI：10.1016/s0040-4020(98)00281-6

  日期：1998.5

  Protected glycals, derived from mono-, di-and tri-saccharides, were easily and efficiently converted into the corresponding 2-deoxy-sugars, by reaction with mercuric(II) acetate/sodium borohydride in a polar solvent at 0 degrees C. The mild and non acidic reaction conditions permit the survival of acid-labile groups, such as silyl ethers. (C) 1998 Elsevier Science Ltd. All rights reserved.
• PASSACANTILLI, PIETRO, TETRAHEDRON LETT., 30,(1989) N9, C. 5349-5352
  作者：PASSACANTILLI, PIETRO

  DOI：——

  日期：——