methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside | 103597-21-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside
• CAS: 103597-21-3
• 化学式: C₃₃H₃₈O₉
• 分子量: 578.659
• InChiKey: NUEGBMKMKHOBOC-VIPZWBODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  42.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside 在 硫酸 作用下， 以 氯仿 为溶剂， 以83%的产率得到1,2,3,4,6,7-hexa-O-acetyl-6-D-glycero-D-heptoglucopyranose
  参考文献：
  名称：

  β-Selective One-Pot Fluorophosphorylation ofd,d-Heptosylglycals Mediated by Selectfluor

  摘要：

  AbstractThis study describes the development of a novel procedure of glycal fluorophosphorylation applied to the synthesis of a fluorinated analogue of an important bacterial metabolite. This procedure was applied to several heptose‐derived glycals, and the stereochemical outcome of the reaction was analyzed. Under optimized conditions, the reaction is β‐gluco selective, but a significant amount of the α‐gluco diastereomer is also generated.

  DOI：

  10.1002/ijch.201400148
• 作为产物：
  描述：

  Methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-D-glycero-α-D-gluco-oct-7-enopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.73h， 生成 methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside
  参考文献：
  名称：

  Jarosz, Slawomir, Bulletin of the Polish Academy of Sciences: Chemistry, 1985, vol. 33, # 9-10, p. 391 - 396

  摘要：

  DOI：

文献信息

• Stereoselective Glycal Fluorophosphorylation: Synthesis of ADP-2-fluoroheptose, an Inhibitor of the LPS Biosynthesis
  作者：Hirofumi Dohi、Régis Périon、Maxime Durka、Michael Bosco、Yvain Roué、François Moreau、Sylvestre Grizot、Arnaud Ducruix、Sonia Escaich、Stéphane P. Vincent

  DOI：10.1002/chem.200801279

  日期：2008.10.29

  describes the synthesis of a fluorinated analogue of ADP-L-glycero-beta-D-manno-heptopyranose, the donor substrate of the heptosyl transferase WaaC, which catalyzes the incorporation of this carbohydrate into LPS. Synthetically, the key step for the preparation of ADP-2F-heptose is the simultaneous and stereoselective installation of both the fluorine atom at C-2 and the phosphoryl group at C-1 through a

  在重要的细菌糖脂（例如脂多糖（LPS））中发现了七糖甙，其生物合成目标是开发新型抗菌剂。这项工作描述了七烷基转移酶WaaC的供体底物ADP-L-甘油-β-D-甘露聚糖-庚糖的氟化类似物的合成，它催化了这种碳水化合物向LPS的掺入。合成而言，制备ADP-2F庚糖的关键步骤是通过selectfluor介导的（selectfluor = 1-氯甲基-4）同时和立体选择性地同时安装C-2处的氟原子和C-1处的磷酰基-氟二氮杂双环[2.2.2]辛烷双（三氟甲磺酸酯）亲电加成/涉及庚糖基的亲核取代。所以，
• Homologation of Protected Hexoses with Grignard C1 Reagents
  作者：Mikhail Kim、Barbara Grzeszczyk、Aleksander Zamojski

  DOI：10.1016/s0040-4020(00)00847-4

  日期：2000.11

  hexodialdo-1,5-pyranosides were reacted with four Grignard C1 reagents: methoxymethyl-, allyloxymethyl-, benzyloxymethyl, and dimethylphenylsilylmethyl-magnesium chlorides. Two stereoisomeric heptoses were obtained in each case in a good yield. The methyl alloside-derived heptosides were accompanied by C-5 inverted products. The addition of Grignard reagents to aldehydes 5–8 has been discussed in terms

  使三种立体异构体己二醛-1,5-吡喃糖苷的衍生物与四种格氏试剂C 1反应：甲氧基甲基氯化物，烯丙氧基甲基氯化物，苄氧基甲基氯化物和二甲基苯基甲硅烷基甲基氯化镁。在每种情况下均以良好的产率获得了两种立体异构的庚糖。甲基同种异体甙衍生的庚糖甙伴随有C-5倒置产物。成醛添加格氏试剂5 - 8在平行α-或β-螯合和Felkin-映过渡态的形式进行了讨论。已经发现，甲硅烷基格氏试剂12对于在C-6处形成l-构型的庚糖衍生物表现出强烈的偏好。