2-Acetamido-1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranose | 4171-73-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Acetamido-1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranose
• 英文别名: 1,N-Diacetyl-3,4,6-O-tribenzyl-alpha-d-glucosamine；[(2R,3R,4R,5S,6R)-3-acetamido-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] acetate
• CAS: 4171-73-7
• 化学式: C₃₁H₃₅NO₇
• 分子量: 533.621
• InChiKey: HXHSPLCAVIZJMH-CWMPKMHISA-N

物化性质

• 沸点：
  690.6±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-Acetamido-1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranose 以 甲醇 为溶剂， 生成 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  Syntheses with Partially Benzylated Sugars. VI.¹ Some Solvolytic Reactions of 2-Acetamido-1-O-acyl-2-deoxy-D-glucopyranose and -D-galactopyranose Derivatives

  摘要：

  DOI：

  10.1021/jo01344a033
• 作为产物：
  描述：

  2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate 在 bismuth(lll) trifluoromethanesulfonate 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 188.0h， 生成 2-Acetamido-1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranose
  参考文献：
  名称：

  为什么用N-乙酰氨基葡糖供体直接糖基化如此差的反应，该怎么办？

  摘要：

  单糖N-乙酰基-d-葡糖胺（GlcNAc）是天然存在的低聚糖中丰富的组成部分，但是由于直接反应的收率低，因此通过化学糖基化的方法引入葡糖胺极具挑战性。通常认为是由中间体1,2-恶唑啉引起的此问题通常通过引入额外的合成步骤来避免，以避免在糖基化过程中出现NHAc官能团。本文介绍了对使用GlcNAc执行直接糖基化的内在挑战的新的基本机械学见解。这些结果表明，控制恶唑啉形成和糖基化的平衡是获得可接受的化学收率的关键。通过运用这种推理方法直接与GlcNAc的传统硫糖苷供体直接进行糖基化，否则其糖基化收率不佳，

  DOI：

  10.1021/acs.joc.6b02305

文献信息

• Syntheses and Doxorubicin-Inclusion Abilities of .BETA.-Cyclodextrin Derivatives with a Hydroquinone .ALPHA.-Glycoside Residue Attached at the Primary Side
  作者：Yoshiki Oda、Masumi Miura、Kenjiro Hattori、Takashi Yamanoi

  DOI：10.1248/cpb.57.74

  日期：——

  This paper describes syntheses and doxorubicin-inclusion abilities of β-cyclodextrin (CyD) derivatives with a hydroquinone α-glycoside residue attached at the primary side. The hydroquinone glycoside having an α-D-glucosidic or 2-acetamido-2-deoxy-α-D-glucosidic linkage became a useful component for providing an α-D-glucose- or 2-acetamido-2-deoxy-α-D-glucose–β-CyD conjugate. The surface plasmon resonance analyses of these β-CyD derivatives for the anticancer agent, doxorubicin, indicated that they had excellent inclusion associations on the order of 105 m−1 for the immobilized doxorubicin.

  本文描述了初级侧连接有对苯二酚 α-糖苷残基的 β-环糊精 (CyD) 衍生物的合成和阿霉素包合能力。具有α-D-糖苷键或2-乙酰氨基-2-脱氧-α-D-糖苷键的对苯二酚糖苷成为提供α--糖苷键的有用组分。 >D-葡萄糖-或 2-乙酰氨基-2-脱氧-α-D-葡萄糖-β-CyD 缀合物。这些抗癌剂阿霉素的 β-CyD 衍生物的表面等离子共振分析表明，它们与固定化的阿霉素具有 105 m-1 量级的优异包合缔合。
• Formation of 2-Acetamido-2-deoxy-D-glucopyranosidic Linkages via Glycosidation Using a Combination of Two Lewis Acids
  作者：Takashi Yamanoi、Yoshiki Oda、Masanobu Midorikawa

  DOI：10.3987/com-14-s(k)4

  日期：——

  A mixed activation system composed of ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex efficiently promotes the glycosylation of various alcohol acceptors using 2-acetamido-3,4,6-tri-O-benzy1-2-deoxy-alpha-D-glucopyranosyl acetate in dichloromethane at room temperature to afford 2-acetamido-2-deoxy-D-glucopyranosides in good yields with significant formation of the alpha-isomers. Notably, stereoselective glycosylations of phenol derivatives as the acceptors afforded aryl 1,2-cis-alpha-glycosides without the formation of any beta-isomers. This highly stereocontrolled 1,2-cis-alpha-glycosidation was applied to the synthesis of a novel hydroquinone alpha-glycoside.
• Formation of 1,2-cis-α-Aryl-glycosidic Linkages Directly from 2-Acetamido-2-deoxy-D-glucopyranosyl Acetate by the Mixed Activating System Using Ytterbium(III) Triflate and Catalytic Boron Trifluoride Diethyl Etherate Complex
  作者：Takashi Yamanoi、Masanobu Midorikawa、Yoshiki Oda

  DOI：10.3987/com-13-s(s)44

  日期：——

  We found that a mixed activating system using ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex efficiently promoted glycosidation of the 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-alpha-D-glucopyranosyl acetate in dichloromethane at room temperature to afford 2-acetamido-2-deoxy-D-glucopyranosides in good yields along with the formation of a considerable amount of alpha-isomers. Glycosylations of the aryl alcohols as the acceptors stereoselectively afforded aryl alpha-glycosides without producing any beta-isomers.
• Why Is Direct Glycosylation with <i>N</i>-Acetylglucosamine Donors Such a Poor Reaction and What Can Be Done about It?
  作者：Mikkel H. S. Marqvorsen、Martin J. Pedersen、Michelle R. Rasmussen、Steffan K. Kristensen、Rasmus Dahl-Lassen、Henrik H. Jensen

  DOI：10.1021/acs.joc.6b02305

  日期：2017.1.6

  chemical glycosylation is challenging since direct reactions are low yielding. This issue, generally agreed upon to be caused by an intermediate 1,2-oxazoline, is often bypassed by introducing extra synthetic steps to avoid the presence of the NHAc functional group during glycosylation. The present paper describes new fundamental mechanistic insights into the inherent challenges of performing direct glycosylation

  单糖N-乙酰基-d-葡糖胺（GlcNAc）是天然存在的低聚糖中丰富的组成部分，但是由于直接反应的收率低，因此通过化学糖基化的方法引入葡糖胺极具挑战性。通常认为是由中间体1,2-恶唑啉引起的此问题通常通过引入额外的合成步骤来避免，以避免在糖基化过程中出现NHAc官能团。本文介绍了对使用GlcNAc执行直接糖基化的内在挑战的新的基本机械学见解。这些结果表明，控制恶唑啉形成和糖基化的平衡是获得可接受的化学收率的关键。通过运用这种推理方法直接与GlcNAc的传统硫糖苷供体直接进行糖基化，否则其糖基化收率不佳，
• Syntheses with Partially Benzylated Sugars. VI.¹ Some Solvolytic Reactions of 2-Acetamido-1-O-acyl-2-deoxy-D-glucopyranose and -D-galactopyranose Derivatives
  作者：Thomas D. Inch、Hewitt G. Fletcher

  DOI：10.1021/jo01344a033

  日期：1966.6