(methyl 2,3-O-isopropylidene-β-D-erythro-pentopyranosid)-4-ulose | 65820-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (methyl 2,3-O-isopropylidene-β-D-erythro-pentopyranosid)-4-ulose
• 英文别名: (3aR,4R,7aS)-4-methoxy-2,2-dimethyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-one
• CAS: 65820-93-1
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: VUNSMQXGBMXONE-BWZBUEFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (methyl 2,3-O-isopropylidene-β-D-erythro-pentopyranosid)-4-ulose 在 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以98%的产率得到methyl 2,3-O-isopropylidene-β-D-ribopyranoside
  参考文献：
  名称：

  Bio-inspired synthesis of rare and unnatural carbohydrates and cyclitols through strain driven epimerization

  摘要：

  通过通过对碳水化合物和环己醇进行仿生异构化，通过应变驱动的将反式-酮缩醛异构化为顺式-酮缩醛，引入了它们罕见且非自然的异构体。

  DOI：

  10.1039/c4cc00868e
• 作为产物：
  描述：

  L-lyxose 在 盐酸 、 草酰氯 、 TEA 、 二甲基亚砜 作用下， 生成 (methyl 2,3-O-isopropylidene-β-D-erythro-pentopyranosid)-4-ulose
  参考文献：
  名称：

  Nakamura, Y.; Yamamoto, H.; Inokawa, S., Heterocycles, 1984, vol. 21, # 2, p. 505

  摘要：

  DOI：

文献信息

• Synthesis of (4S,5S)-4,5-O-isopropylidene-cyclopent-2-ene-1-one via the intramolecular Reformatsky reaction
  作者：Nadezhda A. Ivanova、Zuleykha R. Valiullina、Natal’ya P. Akhmetdinova、Mansur S. Miftakhov

  DOI：10.1016/j.tetlet.2008.08.017

  日期：2008.10

  Isomeric mixtures of bromo- and iodohydrins produced via bromohydroxylation and iodohydroxylation of exo-methylene derivative 2 undergo an intramolecular aldol cyclization–dehydration sequence under Reformatsky reaction conditions to give cyclopentenone 1.

  在exformatsky反应条件下，通过exo-亚甲基衍生物2的溴羟基化和碘羟基化生成的溴-和碘醇的异构体混合物在Reformatsky反应条件下经历分子内羟醛环化-脱水序列，得到环戊烯酮1。
• An Efficient Synthesis of 4-Deoxy-4-(hydroxyphosphinyl)-D-ribofuranoses. The First D-Ribofuranose Analogues Having Hydroxyphosphinyl Group in the Hemiacetal Ring
  作者：Hiroshi Yamamoto、Tadashi Hanaya、Heizan Kawamoto、Saburo Inokawa

  DOI：10.1246/cl.1989.121

  日期：1989.1

  Methyl 2,3-O-isopropylidene-β-d-ribopyranoside was converted (in 4 steps) into methyl 4-deoxy-4-[(dimethoxy)phosphinyl]-2,3-O-isopropylidene-β-d-ribopyranoside (10a, 30% overall yield). The title compounds were readily derived from 10a and characterized as the 4-deoxy-4-(methoxyphosphinyl) tetraacetates.

  将甲基 2,3-O-异亚丙基-β-d-吡喃核糖苷（分 4 步）转化为甲基 4-脱氧-4-[（二甲氧基）膦酰基]-2,3-O-异亚丙基-β-d-吡喃核糖苷（10a，总收率 30%）。标题化合物很容易从 10a 中衍生出来，并表征为 4-脱氧-4-（甲氧基膦酰基）四乙酸酯。
• Synthesis and Structural Analysis of 4-Deoxy-4-(hydroxyphosphinyl and phenylphosphinyl)-D-ribofuranoses
  作者：Tadashi Hanaya、Hiroshi Yamamoto

  DOI：10.1246/bcsj.62.2320

  日期：1989.7

  e gave efficiently (in 4 steps) methyl 4-deoxy-4-[dimethoxyphosphinyl and (methoxy)phenylphosphinyl]-2,3-O-isopropylidene-β-D-ribopyranosides (ca. 30% overall yield). These were led (in 2–3 steps) to the title compounds and then converted into 1,2,3,5-tetra-O-acetyl-4-deoxy-4-(methoxyphosphinyl and phenylphosphinyl)-D-ribofuranoses, whose structures and 3T2 (and 2T3) conformations were established

  甲基 2,3-O-isopropylidene-β-D-ribopyranosides 有效地（分 4 个步骤）得到甲基 4-deoxy-4-[二甲氧基膦基和（甲氧基）苯基膦基]-2,3-O-isopropylidene-β-D-ribopyranosides （大约 30% 的总收率）。这些被引导（分 2-3 步）得到标题化合物，然后转化为 1,2,3,5-四-O-乙酰基-4-脱氧-4-（甲氧基膦基和苯基膦基）-D-呋喃核糖，其结构和 3T2（和 2T3）构象是通过光谱法建立的。
• Synthesis of 1,2,3,5-tetra-O-acetyl-4-deoxy-4-C-[(RS)-ethylphosphinyl]-.alpha.,.beta.-D-ribo- and -L-lyxofuranoses and their structural analysis by 400-MHz proton nuclear magnetic resonance
  作者：Hiroshi Yamamoto、Yuhji Nakamura、Saburo Inokawa、Mitsuji Yamashita、Margaret Ann Armour、Thomas T. Nakashima

  DOI：10.1021/jo00182a010

  日期：1984.4
• Improved Syntheses of D-Ribo- and 2-Deoxy-D-ribofuranose Phospho Sugars from Methyl b-D-Ribopyranoside
  作者：Tadashi Hanaya、Yuko Koga、Heizan Kawamoto、Hiroshi Yamamoto

  DOI：10.3987/com-07-s(u)34

  日期：——

  Methyl 4-deoxy-4-dimethoxyphosphinoyl-2,3-O-isopropylidene-beta-D-ribopyranoside (12a) and methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-beta-D-erythro-pentopyranoside (20) were efficiently prepared respectively from methyl 2,3-O-isopropylidene-beta-D-ribopyranoside (7a) and its 3,4-O-isopropylidene isomer (7b) in appreciably improved total yields compared with those via previously reported routes. Compounds (12a, 20) were led to D-ribofuranose and 2-deoxy-D-ribofuranose phospho sugars (4, 5).