C-(tetra-O-acetyl-β-D-galactopyranosyl) allene | 328386-08-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: C-(tetra-O-acetyl-β-D-galactopyranosyl) allene
• 英文别名: 1-C-(tetra-O-acetyl-β-D-galactopyranosyl)allene；1,3,4,5-tetra-O-acetyl-2,6-anhydro-7,8,9-trideoxy-L-glycero-D-allo-nona-7,8-dienitol；(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-C-propadienyl-D-galactitol；1-C-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)allene
• CAS: 328386-08-9
• 化学式: C₁₇H₂₂O₉
• 分子量: 370.356
• InChiKey: HSVHQMGBLZANRA-BQJWPVKWSA-N

物化性质

• 沸点：
  422.6±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  C-(tetra-O-acetyl-β-D-galactopyranosyl) allene 在 吡啶 、 4-二甲氨基吡啶 、 锂硼氢 、 sodium methylate 、 二甲基氯化铝 、 二乙基碘化铝 、 臭氧 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 5-(benzyl-benzyloxy-amino)-4-{hydroxy-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methyl}-6-phenylsulfanyl-2-trimethylsilanyloxymethyl-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Thomsen-Friedenreich (T) 表位的 C-二糖类似物的合成

  摘要：

  2,3,4,6-四-O-[(叔丁基)二甲基甲硅烷基]-C-β-D-吡喃半乳糖基甲醛(2,6-脱水-1,3,4,6-四-O-[(叔丁基）二甲基甲硅烷基]-D-甘油-L-man no-heptose，2）与异左旋葡萄糖酮（3）在Et（2）AII的存在e中缩合得到1,6-脱水-3-C-{ (1R)-2,6-脱水-3,4,5,7-四-O-[(叔丁基)二甲基甲硅烷基]-D-甘油-L-甘露糖-庚糖醇-1-C-基}-2， 3-dideoxy-β-D-glycero-hex-2-enopyranos-4-ulose (8)。BnONHBn 与 8 的非对映选择性共轭加成，然后用 LiBH4 非对映选择性酮还原并用 Me3SiSPh/ZnI2 处理，提供苯基 3-C-{(1R)-2,6-anhydro-3,4,5,7-tetra-O [(叔丁基)二甲基甲硅烷基]-D-glyce ro-L-manno-heptitol-1-C-yl}-2-[

  DOI：

  10.1055/s-2001-9698
• 作为产物：
  描述：

  炔丙基三甲基硅烷 、 beta-D-半乳糖五乙酸酯 在 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以92%的产率得到C-(tetra-O-acetyl-β-D-galactopyranosyl) allene
  参考文献：
  名称：

  Thomsen-Friedenreich (T) 表位的 C-二糖类似物的合成

  摘要：

  2,3,4,6-四-O-[(叔丁基)二甲基甲硅烷基]-C-β-D-吡喃半乳糖基甲醛(2,6-脱水-1,3,4,6-四-O-[(叔丁基）二甲基甲硅烷基]-D-甘油-L-man no-heptose，2）与异左旋葡萄糖酮（3）在Et（2）AII的存在e中缩合得到1,6-脱水-3-C-{ (1R)-2,6-脱水-3,4,5,7-四-O-[(叔丁基)二甲基甲硅烷基]-D-甘油-L-甘露糖-庚糖醇-1-C-基}-2， 3-dideoxy-β-D-glycero-hex-2-enopyranos-4-ulose (8)。BnONHBn 与 8 的非对映选择性共轭加成，然后用 LiBH4 非对映选择性酮还原并用 Me3SiSPh/ZnI2 处理，提供苯基 3-C-{(1R)-2,6-anhydro-3,4,5,7-tetra-O [(叔丁基)二甲基甲硅烷基]-D-glyce ro-L-manno-heptitol-1-C-yl}-2-[

  DOI：

  10.1055/s-2001-9698

文献信息

• Synthesis, Characterization, and Catalytic Activity of Pd(II) Salen-Functionalized Mesoporous Silica
  作者：Rotcharin Sawisai、Ratchaneekorn Wanchanthuek、Widchaya Radchatawedchakoon、Uthai Sakee

  DOI：10.1155/2017/6208132

  日期：——

  2-hydroxy-1-naphthaldehyde was used as a palladium chelating ligand for the immobilization of the catalytic site. Mesoporous silica supported palladium catalysts were prepared by immobilizing Pd(OAc)2 onto a mesoporous silica gel through the coordination of the imine-functionalized mesoporous silica gel. The prepared catalysts were characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM)

  由 2-羟基苯甲醛和 2-羟基-1-萘醛合成的 Salen 配体用作钯螯合配体，用于固定催化位点。通过亚胺官能化介孔硅胶的配位，将Pd(OAc)2固定在介孔硅胶上，制备介孔二氧化硅负载的钯催化剂。制备的催化剂通过 X 射线衍射 (XRD)、扫描电子显微镜 (SEM)、能量色散 X 射线 (EDX)、电感偶等离子体 (ICP)、氮吸附-解吸和傅里叶变换红外 (FT-IR) 表征) 光谱学。与相应的均相催化剂相比，固体催化剂对 C-(四-O-乙酰基--D-吡喃半乳糖基)丙二烯与芳香胺的加氢胺化显示出更高的活性。
• Gold(III)-catalyzed Intermolecular Hydroamination of C-(tetra-O-acetyl- β -D-galactopyranosyl)allene
  作者：Chaleowsak Khamwong、Senee Kruanetr、Uthai Sakee

  DOI：10.2174/157017812803521162

  日期：2012.10.1

  The intermolecular hydroamination of C-(tetra-O-acetyl-β-D- galactopyranosyl)allene with a variety of aromatic amines proceeded smoothly in the presence of gold(III) catalyst to afford the corresponding allylic amine in good yields. The reaction can be carried out at room temperature and under extremely mild conditions.

  在金（III）催化剂存在下，C-(四-O-乙酰基-β-D-吡喃半乳糖基)烯与多种芳香胺的分子间氢化反应顺利进行，并以良好的收率得到相应的烯丙基胺。反应可在室温和极其温和的条件下进行。
• Synthesis of a C-galactopyranosyl-linked N-substituted 1,2-ethylenediamine
  作者：Uthai Sakee、Chiradet Nasuk

  DOI：10.1016/j.carres.2010.03.040

  日期：2010.6

  A straightforward route to a C-galactopyranosyl-linked 1,2-ethylenediamine is described. The five-step synthetic procedure involves: (i) C-allenylation of D-galactopyranose pentaacetate with propargyl trimethylsilane in the presence of a Lewis acid, (ii) iodination of allenyl galactopyranosyl tetraacetate to diiodoallyl galactopyranosyl tetraacetate, (iii) displacement of the allylic iodide with N-Boc-ethylenediamine, (iv) catalytic hydrogenation of vinyl iodide to alkane, (v) deprotection of the acetyl and N-Boc-groups using acid-catalyzed hydrolysis. This method demonstrates a general method to access a new class of carbohydrate-ethylenediamine C-glycosyl chelators. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of 1-C-(tetra-O-acetyl-β-d-galactopyranosyl)-2,3-diiodo-1-propene and its reaction with primary amines
  作者：Uthai Sakee、Chiradet Nasuk、Ronald Grigg

  DOI：10.1016/j.carres.2009.06.021

  日期：2009.10

  Iodination of 1-C-(tetra-O-acetyl-beta-D-galactopyranosyl)allene affords an E/Z-mixture of 1-C-(tetra-O-acetyl-beta-D-galactopyranosyl)-2,3-diiodo-1-propene. S(N)2 displacement of the allylic iodide with primary amines affords an E/Z-mixture of allylic amines under a variety of conditions. Due to its experimental simplicity and low cost of reagents, this procedure may find wide use in the laboratory for functionalization of sugar allenes. (C) 2009 Elsevier Ltd. All rights reserved.
• Palladium-catalyzed hydroamination of C-(tetra-O-acetyl-β-d-galactopyranosyl)allene
  作者：Chaleowsak Khamwong、Uthai Sakee

  DOI：10.1016/j.carres.2010.11.006

  日期：2011.2

  Both palladium(0) and palladium(II) methods for catalyzed hydroamination of C-(tetra-O-acetyl-beta-D-galactopyranosyl)allene with a variety of aromatic amines have been successfully developed. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.