(2S,3S,4S,5R,6S)-6-methoxy-3-[(4-methoxyphenyl)methoxy]-4,5-bis(phenylmethoxy)oxane-2-carbaldehyde | 130523-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6S)-6-methoxy-3-[(4-methoxyphenyl)methoxy]-4,5-bis(phenylmethoxy)oxane-2-carbaldehyde
• CAS: 130523-98-7
• 化学式: C₂₉H₃₂O₇
• 分子量: 492.569
• InChiKey: XBWIXDIBHHIZBO-RQKPWJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  36.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-6-methoxy-3-[(4-methoxyphenyl)methoxy]-4,5-bis(phenylmethoxy)oxane-2-carbaldehyde 在 mercury(II) diacetate 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 sodium chloride 作用下， 以 溶剂黄146 、 丙酮 、 乙腈 为溶剂， 反应 41.0h， 生成 1-O-acetyl-3,4-bis-O-benzyl-5-O-[(4-methoxyphenyl)methyl]-D-myo-inositol
  参考文献：
  名称：

  Synthesis of l-α-phosphatidyl-d-myo-inositol 5-phosphate and l-α-phosphatidyl-d-myo-inositol 3,5-bisphosphate

  摘要：

  Two new 5-phosphorylated phosphatidylinositols have been synthesized from methyl alpha-D-glucopyranoside as the chiral precursor. These new PtdInsP(n)s have been recently detected in mammalian cells. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00737-0
• 作为产物：
  描述：

  methyl-2,3-bis-O-benzyl-4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside 在 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3S,4S,5R,6S)-6-methoxy-3-[(4-methoxyphenyl)methoxy]-4,5-bis(phenylmethoxy)oxane-2-carbaldehyde
  参考文献：
  名称：

  立体选择性合成双吡喃基C-二糖

  摘要：

  从D-葡萄糖开始，已经完成了在C-1处包含炔基部分的反式融合的二戊基糖的合成。β-取代的C-二糖的形成提供了一个跨度约为12.8的水溶性糖基连接子。

  DOI：

  10.1016/s0040-4039(00)74040-8

文献信息

• The Synthesis of Some Octenoses as Potential Precursors to Lincosamine, a Derived Portion of the Antibiotic Lincomycin
  作者：RV Stick、DMG Tilbrook

  DOI：10.1071/ch9901643

  日期：——

  Methyl (E)-2,3-di-O-benzyl-6,7,8-trideoxy-α-D-galacto-oct-6-enopyranoside, a potential precursor to lincosamine, has been prepared from both methyl α-D-galactopyranoside and methyl α-D-glucopyranoside, with the required inversion at C4 in the latter sequence being effected by a conventional oxidation-reduction. As well, (E)-6,7-dideoxy-1,2: 3,4-di-O-isopropylidene-α-D-galacto-oct-6-enose and (E)- and (Z)-6,7,8- trideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-oct-6-enose have been prepared from 1,2: 3,4-di-O-isopropylidene-α-D-galactose.

  甲基(E)-2,3-二-O-苄基-6,7,8-三脱氧-α-D-半乳糖-辛-6-烯吡喃糖苷是一种潜在的林可胺前体，已从甲基α-D-吡喃半乳糖苷和甲基α-D-吡喃葡萄糖苷中制备出来，后者序列中 C4 所需的反转是通过传统的氧化还原法实现的。此外，(E)-6,7-二脱氧-1,2:3,4-二-O-异亚丙基-α-D-半乳糖-辛-6-烯糖和(E)-和(Z)-6,7,8-三脱氧-1,2:3,4-二-O-异亚丙基-α-D-半乳糖-辛-6-烯糖也是由 1,2:3,4-二-O-异亚丙基-α-D-半乳糖制备的。
• Chiral Synthesis of the BC-Ring System of Ciguatoxin from<scp>d</scp>-Glucose
  作者：Ei’ichi Ami、Hisakazu Kishimoto、Hiroshi Ohrui、Hiroshi Meguro

  DOI：10.1271/bbb.61.2019

  日期：1997.1

  The BC-ring system of ciguatoxin was stereoselectively synthesized by 12 steps from methyl α-d-glucopyranoside.

  以甲基α-d-吡喃葡萄糖苷为原料，通过 12 个步骤立体选择性地合成了雪卡毒素的 BC 环系统。
• Radical Cyclization of Sugar-Derived β-(Alkynyloxy)acrylates:  Synthesis of Novel Fused Ethers
  作者：Michiel A. Leeuwenburgh、Remy E. J. N. Litjens、Jeroen D. C. Codée、Herman S. Overkleeft、Gijsbert A. van der Marel、Jacques H. van Boom

  DOI：10.1021/ol0000408

  日期：2000.5.1

  Tributyltin radical mediated cyclization of carbohydrate-derived beta-(alkynyloxy)acrylates leading to highly functionalized cis and trans-fused bicyclic ethers of various ring sizes is described. The efficacy of the radical cyclization is nicely illustrated in the iterative construction of a trans-fused tricyclic tetrahydropyran.
• Synthesis of P-5 tethered inositol-1,2,6-trisphosphate, an affinity reagent for α-trinositol receptors
  作者：Anu Chaudhary、György Dormán、Glenn D. Prestwich

  DOI：10.1016/s0040-4039(00)78333-x

  日期：1994.10

  The synthesis of D-myo-P-5-(O-aminopropyl)-Ins(1,2,5,6)P-4, a phosphodiester analog of Ins(1,2,6)P-3 tethered at the C-5 position, has been achieved and a photoaffinity label has been prepared.
• Lindh, Ingvar; Hindsgaul, Ole, Journal of the American Chemical Society, 1991, vol. 113, # 1, p. 216 - 223
  作者：Lindh, Ingvar、Hindsgaul, Ole

  DOI：——

  日期：——