Methyl-2,4,6-tri-O-benzoyl-3-desoxy-α-D-xylo-hexopyranosid | 129185-20-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl-2,4,6-tri-O-benzoyl-3-desoxy-α-D-xylo-hexopyranosid
• 英文别名: methyl 2,4,6-tri-O-benzoyl-3-deoxy-α-D-xylo-hexopyranoside；[(2R,3R,5R,6S)-3,5-dibenzoyloxy-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 129185-20-2
• 化学式: C₂₈H₂₆O₈
• 分子量: 490.51
• InChiKey: WNUPIVVSYYXUMO-MUCKBHKGSA-N

物化性质

• 沸点：
  609.6±55.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Methyl-2,4,6-tri-O-benzoyl-3-desoxy-α-D-xylo-hexopyranosid 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 C.I.酸性橙108 、 三氟乙酸 、 1,5-Diazabicyclo[5.4.0]undec-5-ene 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 Benzyl-O-(2,4,6-tri-O-benzoyl-3-desoxy-α-D-xylo-hexopyranosyl)-(1->3)-2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosid
  参考文献：
  名称：

  Paulsen, Hans; Rutz, Volker; Brockhausen, Inka, Liebigs Annalen der Chemie, 1992, # 7, p. 747 - 758

  摘要：

  DOI：
• 作为产物：
  描述：

  ((2R,3R,4S,5R,6S)-5-acetoxy-3,4-dihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl acetate 在 吡啶 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 三正丁基氢锡 、 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 22.17h， 生成 Methyl-2,4,6-tri-O-benzoyl-3-desoxy-α-D-xylo-hexopyranosid
  参考文献：
  名称：

  Paulsen, Hans; Rutz, Volker; Brockhausen, Inka, Liebigs Annalen der Chemie, 1992, # 7, p. 747 - 758

  摘要：

  DOI：

文献信息

• Synthesis of methyl O-α-L-rhamnopyranosyl-(1 → 2)-α-d-galactopyranosides specifically deoxygenated at position 3, 4, or 6 of the galactose residue
  作者：Laurence A. Mulard、Pavol Kovác̆、Cornelis P.J. Glaudemans

  DOI：10.1016/0008-6215(94)84287-6

  日期：1994.1

  4-tri-O-benzoyl-alpha-L-rhamnopyranosyl bromide with suitably protected, deoxygenated derivatives of methyl alpha-D-galactopyranoside. Deoxygenation was achieved via activation of a protected methyl alpha-D-gluco- or galacto-pyranoside with N,N'-thiocarbonyldiimidazole followed by treatment with tributyltin hydride and azobisisobutyronitrile. At position 3, the deoxygenation was more successful when performed with

  通过将2,3,4-三-O-苯甲酰基-α-L-鼠李糖基吡喃糖基溴化物与适当保护的甲基α-D-吡喃半乳糖苷的脱氧衍生物缩合来合成标题二糖。通过用N，N'-硫代羰基二咪唑活化被保护的甲基α-D-葡萄糖或半乳糖吡喃糖苷，然后用氢化三丁基锡和偶氮二异丁腈处理，可以实现脱氧。在位置3，当用三-O-苯甲酰化的前体而不是三-O-苄基化的前体进行脱氧更成功。通过甲基3-脱氧-α-D-木糖己吡喃糖苷的苄基化获得相应的亲核试剂。可以从具有D-半乳糖或D-葡萄糖构型的衍生物开始进行在位置4上脱氧的糖基受体的制备。
• Synthesis of a series of methyl β-glycosides of (1→6)-β-d-galacto-oligosaccharides having one residue deoxygenated at position 3
  作者：Pavol Kováč、Kevin J. Edgar

  DOI：10.1016/0008-6215(90)84226-k

  日期：1990.6

  Methyl beta-glycosides of beta-(1----6)-linked D-galactobioses (13 and 16) and -galactotrioses (21, 24, and 26) containing a 3-deoxy-beta-D-xylo-hexopyranosyl moiety either as one of the end units or the internal unit have been synthesized. The extension of the oligosaccharide chain was achieved, inter alia, by the use of two newly synthesized glycosyl donors derived from 3-deoxy-D-xylo-hexopyranose, namely, 2,4,6-tri-O-benzoyl-3-deoxy-a-D-xylo-hexopyranosyl chloride (8) and 2,4-di-O-benzoyl-6-O-bromoacetyl-3-deoxy-a-D-xylo-hexopyranosyl chloride (10). Glycosylation reactions were mediated by silver triflate under base-deficient conditions.
• Hydrolytic activity of α-galactosidases against deoxy derivatives of p-nitrophenyl α-d-galactopyranoside
  作者：Wataru Hakamata、Toshiyuki Nishio、Tadatake Oku

  DOI：10.1016/s0008-6215(99)00281-5

  日期：2000.2

  The four possible monodeoxy derivatives of p-nitrophenyl (PNP) alpha-D-galactopyranoside were synthesized, and hydrolytic activities of the alpha-galactosidase of green coffee bean, Mortierella vinacea and Aspergillus niger against them were elucidated. The 2- and 6-deoxy substrates were hydrolyzed by the enzymes from green coffee bean and M. vinacea, while they scarcely acted on the 3- and 4-deoxy compounds. On the other hand, A. niger alpha-galactosidase hydrolyzed only the 2-deoxy compound in these deoxy substrates, and the activity was very high. These results indicate that the presence of two hydroxyl groups (OH-3 and -4) is essential for the compounds to act as substrates for the enzymes of green coffee bean and M. vinacea, while the three hydroxyl groups (OH-3, -4, and -6) are necessary for the activity of the A. niger enzyme. The kinetic parameters (K-m and V-max) of the enzymes for the hydrolysis of PNP alpha-D-galactopyranoside and its deoxy derivatives were obtained from kinetic studies. (C) 2000 Elsevier Science Ltd. All rights reserved.
• KOVAC, PAVOL;EDGAR, KEVIN J., CARBOHYDR. RES., 201,(1990) N, C. 79-93
  作者：KOVAC, PAVOL、EDGAR, KEVIN J.

  DOI：——

  日期：——