peracetyl-1-deoxymannonojirimycin | 155501-71-6

• 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: peracetyl-1-deoxymannonojirimycin
• 英文别名: acetic acid (2R,3R,4R,5R)-4,5-diacetoxy-2-acetoxymethyl-1-acetyl-piperidin-3-yl ester；[(2R,3R,4R,5R)-1-acetyl-3,4,5-triacetyloxypiperidin-2-yl]methyl acetate
• CAS: 155501-71-6
• 化学式: C₁₆H₂₃NO₉
• 分子量: 373.36
• InChiKey: UWAXKEPCPIIJKB-KLHDSHLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  peracetyl-1-deoxymannonojirimycin 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以70%的产率得到1-脱氧甘露伊霉素
  参考文献：
  名称：

  Glucose is a Precursor of 1-deoxynojirimycin and 1-deoxymannonojirimycin in Streptomyces subrutilus

  摘要：

  Streptomyces subrutilus ATCC 27467, when grown on a glucose-containing soyabean medium, produces both 1-deoxymannonojirimycin (DMJ) and 1-deoxynojirimycin (DNJ) in its culture medium. When 1- or 2-[H-2]-D-glucose is used, the deuterium label appears at C6 in both alkaloids and the labelling pattern suggests that the first step in the biosynthesis of both DNJ and DMJ is a glucose to fructose isomerisation. Studies with 5-[H-2]- and 6,6-[H-2(2)]-D-glucose indicate that oxidation of the 6-position of the glucose/fructose occurs during the biosynthesis and that mannonojirimycin is the first aminosugar to be formed. Mannonojirimycin can then undergo dehydration and reduction to DMJ. Alternatively, epimerisation of mannonojirimycin can occur at C2 to give norjirimycin which is then dehydrated and reduced to DNJ.

  DOI：

  10.1016/s0040-4020(01)88220-x
• 作为产物：
  描述：

  methyl (1S,4S,5R,6S)-1-[dimethyl(phenyl)silyl]-5-hydroxy-3-(4-methylphenyl)sulfonyl-7-oxa-3-azabicyclo[4.1.0]heptane-4-carboxylate 在 咪唑 、 过氧乙酸 、 lithium aluminium tetrahydride 、 Hg(OAc)2 、 四丁基氟化铵 作用下， 以 乙醚 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 peracetyl-1-deoxymannonojirimycin
  参考文献：
  名称：

  基于高度官能化烯丙醇的 Sharpless 不对称环氧化反应的对映选择性合成脱氧甘露野尻霉素

  摘要：

  报道了一种有效的对映选择性合成 deoxymannojirimicin。它基于甲硅烷基取代的烯丙基 1,4-氨基醇的不寻常的 Sharpless 不对称环氧化反应和进一步高度立体选择性的分子内醛醇缩合反应。deoxymannojirimicin 的两种对映异构体均可用。制备了一种正交保护的多羟基化哌啶，它可能正式导致该哌啶家族的其他成员。

  DOI：

  10.1002/ejoc.201100102

文献信息

• [EN] CONJUGATE<br/>[FR] CONJUGUÉ
  申请人：GLYKOS BIOMEDICAL OY

  公开号：WO2019243672A1

  公开（公告）日：2019-12-26

  A conjugate is disclosed. The conjugate may comprise a targeting unit for delivery to a tumour, and a glycosylation inhibitor for inhibiting glycosylation in the tumour, thereby decreasing the immunosuppressive activity of the tumour. The glycosylation inhibitor may be conjugated to the targeting unit.

  揭示了一种共轭物。该共轭物可能包括用于传递至肿瘤的靶向单元，以及用于抑制肿瘤中的糖基化的糖基化抑制剂，从而降低肿瘤的免疫抑制活性。糖基化抑制剂可以与靶向单元结合。
• Synthesis of <scp>d</scp>- and <scp>l</scp>-Deoxymannojirimycin via an Asymmetric Aminohydroxylation of Vinylfuran
  作者：Michael H. Haukaas、George A. O'Doherty

  DOI：10.1021/ol006907j

  日期：2001.2.1

  [figure: see text] The Sharpless catalytic asymmetric aminohydroxylation has been applied to 2-vinylfuran, producing beta-hydroxyfurfurylamine 5a with enantioexcess of > 86% and 21% yield from furfural. The Cbz and TBS protected amino alcohol 5a was converted into both the D- and L-isomers of deoxymannojirimycin (DMJ) and deoxygulonojirimycin in five to seven steps and 48% and 66% overall yields. The

  [图：见正文] Sharpless催化不对称氨基羟基化反应已应用于2-乙烯基呋喃，生产的β-羟基糠胺5a的对映体过量> 86％，糠醛的收率为21％。Cbz和TBS保护的氨基醇5a以五到七个步骤转化为脱氧甘露糖霉素（DMJ）和脱氧古洛糖霉素的D-异构体和L-异构体，总收率分别为48％和66％。关键步骤包括使用aza-Achmatowicz反应，非对映选择性Luche还原，非对映选择性二羟基化和串联Cbz脱保护/还原胺化。
• Glucose is a Precursor of 1-deoxynojirimycin and 1-deoxymannonojirimycin in Streptomyces subrutilus
  作者：David J Hardick、David W. Hutchinson、Sally J. Trew、Elizabeth M.H. Wellington

  DOI：10.1016/s0040-4020(01)88220-x

  日期：1992.1

  Streptomyces subrutilus ATCC 27467, when grown on a glucose-containing soyabean medium, produces both 1-deoxymannonojirimycin (DMJ) and 1-deoxynojirimycin (DNJ) in its culture medium. When 1- or 2-[H-2]-D-glucose is used, the deuterium label appears at C6 in both alkaloids and the labelling pattern suggests that the first step in the biosynthesis of both DNJ and DMJ is a glucose to fructose isomerisation. Studies with 5-[H-2]- and 6,6-[H-2(2)]-D-glucose indicate that oxidation of the 6-position of the glucose/fructose occurs during the biosynthesis and that mannonojirimycin is the first aminosugar to be formed. Mannonojirimycin can then undergo dehydration and reduction to DMJ. Alternatively, epimerisation of mannonojirimycin can occur at C2 to give norjirimycin which is then dehydrated and reduced to DNJ.
• Enantioselective Synthesis of Deoxymannojirimycin Based on Sharpless Asymmetric Epoxidation of a Highly Functionalized Allylic Alcohol
  作者：Marie-Céline Lamas、Max Malacria、Serge Thorimbert

  DOI：10.1002/ejoc.201100102

  日期：2011.5

  An efficient enantioselective synthesis of deoxymannojirimicin is reported. It is based on the unusual Sharpless asymmetric epoxidation of a silyl-substituted allylic 1,4-amino alcohol coupled with a further highly stereoselective intramolecular aldolization. Both enantiomers of deoxymannojirimicin are available. An orthogonally protected polyhydroxylated piperidine was prepared, which could formally

  报道了一种有效的对映选择性合成 deoxymannojirimicin。它基于甲硅烷基取代的烯丙基 1,4-氨基醇的不寻常的 Sharpless 不对称环氧化反应和进一步高度立体选择性的分子内醛醇缩合反应。deoxymannojirimicin 的两种对映异构体均可用。制备了一种正交保护的多羟基化哌啶，它可能正式导致该哌啶家族的其他成员。