2,4,6-Tri-O-acetyl-β-methyl-D-glucopyranoside | 92008-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-Tri-O-acetyl-β-methyl-D-glucopyranoside
• 英文别名: methyl 2,4,6-tri-O-acetyl-β-D-glucopyranoside；methyl-2,4,6-tri-O-acetyl-β-D-glucopyranoside；2,4,6-Tri-O-acetyl-methyl-β-D-glucopyranosid；Methyl-2,4,6-tri-O-acetyl-β-D-glucopyranosid；[(2R,3S,4S,5R,6R)-3,5-diacetyloxy-4-hydroxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 92008-11-2
• 化学式: C₁₃H₂₀O₉
• 分子量: 320.296
• InChiKey: LKFNEACJFKRTHV-NZEXEKPDSA-N

物化性质

• 沸点：
  430.8±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,4,6-Tri-O-acetyl-β-methyl-D-glucopyranoside 在 palladium on activated charcoal 2,3,5-三甲基吡啶 、 Cl⁽³⁾HO₄ 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 35.0h， 生成 (2R,3S,4R,5R,6R)-5-amino-6-(((2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-4-yl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol
  参考文献：
  名称：

  立体合成2-氨基糖的1,2-顺式糖苷

  摘要：

  1,2-顺式-糖苷键的高度立体选择性合成是困难的，并且令人满意的解决方案仍然是碳水化合物的合成化学中的问题。最近，我们提出了一种新的方法，通过使用在C-2处具有非参与取代基的1，Ztruns-糖基硫氰酸酯作为糖基化试剂'-3，来实现特定的1,2-顺式糖基化。我们现在报告该方法在2-氨基糖的1，Zcis-糖苷的立体有择合成中的应用，这也可以被认为是一个困难的问题[cf. 参考 41.将相应的1，2-truns-2-叠氮基-2-脱氧糖基硫氰酸盐用作糖基供体，随后将叠氮基转化为氨基。1的立体定向合成 通过合成具有不同类型的糖苷键的αD-氨基葡萄糖基-o-葡萄糖的衍生物证明了2-顺式氨基糖苷。通过处理已知的3,4,6-三-O-乙酰基-2，获得了3,4,6-Tri-0-乙酰基-2-叠氮基-2-脱氧-PD-葡吡喃基硫氰酸酯（1） -叠氮基-2-脱氧-aD-吡喃葡萄糖基溴化物5（5.6 mmol）与KSCN（16

  DOI：

  10.1016/0008-6215(93)80050-o
• 作为产物：
  描述：

  2,4,6-tri-O-acetyl-3-O-allyl-α-D-glucopyranosyl trichloroacetimidate 在 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2,4,6-Tri-O-acetyl-β-methyl-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of β-d-glucose oligosaccharides from Phytophthora parasitica

  摘要：

  The glucohexaose, beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 3)-beta-D-Glcp-(1 --> 3)-(3-D-Glcp-(1 --> 6)]-(3-D-Glcp-(1 --> 3)-o-Glcp, was synthesized as its allyl glycoside via 3+3 strategy. The trisaccharide donor, 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl-(1 --> 3)-2,4,6-tri-O-acetyl-(3-D-glucopyranosyl-(1 --> 3)-2,4,6-tri-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (11), was obtained by 3-selective coupling of isopropyl 4,6-O-benzylidene-1-thio-(3-D-glucopyranoside (2) with 2,3,4,6-tetra-O-benzoyl-(3-D-glucopyranosyl-(1 3)-2-O-acetyl-4,6-O-benzylidene-alpha-D-glucopyranosyl trichloroacetimidate (6), followed by hydrolysis, acetylation, dethiolation, and trichloroacetimidation. Meanwhile, the trisaccharide acceptor, allyl 2,3,4,6-tetra-O-benzoyl-(3-D-glucopyranosyl-(1 --> 3)-2-O-acetyl(3-D-glucopyranosyl-(1 3)-4,6-di-O-acetyl-2-O-benzoyl-alpha-D-glucopyranoside (14), was prepared by coupling of allyl 4,6-di-Oacetyl-2-O-benzoyl-alpha-D-glucopyranoside (12) with 6, followed by debenzylidenation. Condensation of 14 with 11, followed by deacylation, gave the target hexaoside. A (3-(1 ->3)-linked tetrasaccharide 29 was also synthesized with methyl 2-O-benzoyl-4,6-0benzylidene-(3-D-glucopyranosyl-(1-> 3)-2,4,6-tri-O-acetyl-(3-D-glucopyranoside (25) as the acceptor and acylated (3-(1 3)-linked disaccharide 21 as the donor. 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.08.004

文献信息

• Mode of Action on Deacetylation of Acetylated Methyl Glycoside by Cellulose Acetate Esterase from<i>Neisseria sicca</i>SB
  作者：Kunihiko MORIYOSHI、Hayato YAMANAKA、Takashi OHMOTO、Tatsuhiko OHE、Kiyofumi SAKAI

  DOI：10.1271/bbb.69.1292

  日期：2005.1

  The regioselective deacetylation of purified cellulose acetate esterase from Neisseria sicca SB was investigated on methyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside and 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranoside. The substrates were used as model compounds of cellulose acetate in order to estimate the mechanism for deacetylation of cellulose acetate by the enzyme. The enzyme rapidly deacetylated

  研究了干燥的Neisseria sicca SB醋酸纤维素酯酶的区域选择性脱乙酰化作用，对甲基2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖苷和2,3,4,6-四-O-乙酰基-甲基β-D-吡喃半乳糖苷。将底物用作乙酸纤维素的模型化合物，以估计酶使乙酸纤维素脱乙酰化的机理。该酶在甲基2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖苷的C-3位快速脱乙酰基化，从而以大约70％的产率积累作为主要初始反应产物的2,4,6-三乙酸酯。在位置C-2处进行脱乙酰基反应，并以50％的产率产生4，6-二乙酸酯。该酶以较低的速率使C-4和C-6位的产物脱乙酰，并在随后的反应阶段生成4-和6-单乙酸酯。最后，得到完全脱乙酰的产物。对于2,3,4，6-四-O-乙酰基-β-D-吡喃半乳糖苷，CA酯酶在位置C-3和C-6上脱乙酰基，得到2,4,6-和2,3,4-三乙酸酯。脱乙酰基顺序在位置C-3和C-6进行，以55％的产率积累2
• Kochetkov, N. K.; Klimov, E. M.; Malysheva, N. N., Doklady Chemistry, 1991, # 4-6, p. 393 - 396
  作者：Kochetkov, N. K.、Klimov, E. M.、Malysheva, N. N.、Demchenko, A. V.

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• Some kinetic characteristics of glycosylation at high pressures
  作者：V. M. Zhulin、Z. G. Makarova、E. M. Klimov、N. N. Malysheva、N. K. Kochetkov

  DOI：10.1007/bf00962447

  日期：1989.12
• Demchenko, A.V.; Malysheva, N.N.; Kochetkov, N.K., Doklady Chemistry, 1995, vol. 341, # 4-6, p. 121 - 123
  作者：Demchenko, A.V.、Malysheva, N.N.、Kochetkov, N.K.

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  日期：——
• The effect of high pressure on glycosylation under Helferich conditions
  作者：Nikolay K. Kochetkov、Victor M. Zhulin、Nelly M. Malysheva、Evgeny M. Klimov、Zinaida G. Makarova

  DOI：10.1016/0008-6215(87)80293-8

  日期：1987.9