1,3,4,6-Tetra-O-benzyl-2,5-anhydro-D-mannitol | 117467-65-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-Tetra-O-benzyl-2,5-anhydro-D-mannitol
• 英文别名: (2R,3R,4R,5R)-3,4-bis(phenylmethoxy)-2,5-bis(phenylmethoxymethyl)oxolane
• CAS: 117467-65-9
• 化学式: C₃₄H₃₆O₅
• 分子量: 524.657
• InChiKey: DHVGVYQEYOXUTI-YFRBGRBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3,4,6-Tetra-O-benzyl-2,5-anhydro-D-mannitol 在 草酰氯 、 sodium methylate 、 sodium hydride 、 sodium cyanoborohydride 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 [(2S)-1-[[(2R,3R,4R,5R)-5-(hexadecoxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl]pyrrolidin-2-yl]methanol
  参考文献：
  名称：

  Hydrolytically stable arabinofuranoside analogs for the synthesis of arabinosyltransferase inhibitors

  摘要：

  The first members of two new families of arabinosyltransferase inhibitors, derived from previously reported hybrid compounds covalently associating all iminoalditol with an alpha-D-arabinofuranoside, have been prepared. In place of the arabinofuranoside moiety, they incorporate in their structure a Suitably Substituted tetrahydrofuran (C-glycoside family) or a cyclopentane (carba-sugar family) for mimicking the alpha-D-arabinofuranoside ring. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.029
• 作为产物：
  描述：

  2,5-anhydro-3,4,6-tris-O-(phenylmethyl)-D-mannose 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.25h， 生成 1,3,4,6-Tetra-O-benzyl-2,5-anhydro-D-mannitol
  参考文献：
  名称：

  Stereoselective synthesis of tetrahydrofurans and linear methyl enol-ethers from glycals

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(97)10062-3

文献信息

• Reaction between glycal benzyl ethers and thallium(III) nitrate. Synthesis of showdomycin analogues.
  作者：Andrew Kaye、Stephen Neidle、Colin B. Reese

  DOI：10.1016/s0040-4039(00)82059-6

  日期：1988.1

  On treatment with thallium (III) nitrate, trihydrate in acetonitrile solution, 3,4,6-tri-O-benzyl-D-glugal () gives the ring-contracted aldehyde () which has been converted into the showdemycin analogue (); 2-(--2′-deoxyribofuranosyl)maleimide () has similarly been prepared from () in satisfactory overall yield.

  在乙腈溶液中用三水合硝酸th（III）处理后，3,4,6-三-O-苄基-D-葡糖醛（）生成环缩合醛（），该醛已被转化为Showdemycin类似物（）。2 - （- 2'-脱氧核糖呋喃糖基）马来酰亚胺（）类似地由（）以令人满意的总产率制备。
• Asymmetric cyclopropanation of allylic ethers: cleavage and regeneration of the chiral auxiliary
  作者：Andre B. Charette、Bernard Cote

  DOI：10.1021/jo00056a028

  日期：1993.2

  The ring contraction reaction of 2-O-(trifluoromethyl)sulfonyl]oxy]-beta-D-glucopyranosides and their corresponding a-anomers is reported. The rearrangement was shown to occur under extremely mild basic conditions to allow isolation of acid-sensitive optically active substituted cyclopropylmethanols. The chiral auxiliary can be regenerated by converting the C-glucofuranoside, byproduct of the rearrangement, into tri-O-benzyl-D-glucal (two steps).
• KAYE, ANDREW;NEIDLE, STEPHEN;REESE, COLIN B., TETRAHEDRON LETT., 29,(1988) N 15, 1841-1844
  作者：KAYE, ANDREW、NEIDLE, STEPHEN、REESE, COLIN B.

  DOI：——

  日期：——
• 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.
• Hydrolytically stable arabinofuranoside analogs for the synthesis of arabinosyltransferase inhibitors
  作者：Manon Chaumontet、Valérie Pons、Karine Marotte、Jacques Prandi

  DOI：10.1016/j.tetlet.2005.12.029

  日期：2006.2

  The first members of two new families of arabinosyltransferase inhibitors, derived from previously reported hybrid compounds covalently associating all iminoalditol with an alpha-D-arabinofuranoside, have been prepared. In place of the arabinofuranoside moiety, they incorporate in their structure a Suitably Substituted tetrahydrofuran (C-glycoside family) or a cyclopentane (carba-sugar family) for mimicking the alpha-D-arabinofuranoside ring. (c) 2005 Elsevier Ltd. All rights reserved.