methyl 2,3-O-isopropylidene-α-L-rhamnopyranoside | 42214-01-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-O-isopropylidene-α-L-rhamnopyranoside
• 英文别名: methyl 2,3-O-isopropylidene-β-L-rhamnopyranoside；2,3-O-isopropylidene-α-L-rhamnopyranoside；Methyl-6-deoxy-2,3-O-isopropyliden-β-L-mannopyranosid；(3aR,4S,6S,7S,7aR)-4-methoxy-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 42214-01-7
• 化学式: C₁₀H₁₈O₅
• 分子量: 218.25
• InChiKey: TVKKWQAJQZHTDN-ABXGFROZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 在 盐酸 、 sodium tetrahydroborate 、 phosphorus pentoxide 作用下， 以 吡啶 、 甲醇 、 二甲基亚砜 为溶剂， 反应 0.84h， 生成 α-D-Galactopyranoside, methyl 6-deoxy-, triacetate (9CI)
  参考文献：
  名称：

  Studies on the constituents of Zizyphi Fructus. III. Structures of dammarane-type saponins.

  摘要：

  酸枣仁皂苷I、II、III和枣仁皂苷B自酸枣仁中分离而得。酸枣仁皂苷I、II、III经Smith-de Mayo降解反应得到真正的皂苷元——酸枣仁苷元。通过PMR、CMR检测及应用Klyne分子旋光法测定了各皂苷中糖连接的构型，从而确定了酸枣仁皂苷I、II、III的结构分别为(I)、(II)和(III)。6-脱氧-L-太妃糖作为酸枣仁皂苷I和III的糖部分被分离出来。

  DOI：

  10.1248/cpb.29.676
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 (2S,3R,4R,5R,6S)-2-Methoxy-6-methyl-tetrahydro-pyran-3,4,5-triol 在 对甲苯磺酸 作用下， 反应 96.0h， 以68.9%的产率得到methyl 2,3-O-isopropylidene-α-L-rhamnopyranoside
  参考文献：
  名称：

  Preparation of carbohydrate isopropylidene derivatives with 2,2-dimethoxypropane in the presence of toluene-p-sulphonic acid

  摘要：

  DOI：

  10.1016/s0008-6215(00)85991-1

文献信息

• Backman, Irene; Erbing, Bertil; Jansson, Per-Erik, Journal of the Chemical Society. Perkin transactions I, 1988, p. 889 - 898
  作者：Backman, Irene、Erbing, Bertil、Jansson, Per-Erik、Kenne, Lennart

  DOI：——

  日期：——
• Induction of a Preferred Sense of Twist in Flexible Diphenyls by Carbohydrate Scaffolds. Synthesis of Two “Naked” Ellagitannin Analogous
  作者：Giuseppe Capozzi、Cinzia Ciampi、Giovanna Delogu、Stefano Menichetti、Cristina Nativi

  DOI：10.1021/jo010522c

  日期：2001.12.1

  The synthesis of "naked" ellagitannin analogues 1 and 2, having a preferred sense of twist of the diphenyl moiety, with a rhamnose and a glucose template, is reported. A clear induction in the chirality of the diphenyl moiety, mediated through a 10-membered ring via ester linkages, was observed. The chiral scaffold of glucose (diequatorial 2,3-hydroxyl groups) exerts a remarkable stronger atropdiastereoselective effect onto the diphenoyl group than the rhamnose ring (axial-equatorial 2,3-hydroxyl groups), according to the Schmidt-Haslam hypothesis.
• Studies on the constituents of Zizyphi Fructus. III. Structures of dammarane-type saponins.
  作者：NOBUYUKI OKAMURA、TOSHIHIRO NOHARA、AKIRA YAGI、ITSUO NISHIOKA

  DOI：10.1248/cpb.29.676

  日期：——

  Zizyphus saponins I, II, III and jujuboside B were isolated from Zizyphi Fructus. On Smith-de Mayo degradation, zizyphus saponins I, II and III yielded jujubogenin as a genuine aglycone. The configuration of the sugar linkages in each saponin was determined on the basis of PMR and CMR examinations and application of Klyne's rule on molecular rotation, and the structures of zizyphus saponins I, II and III were established as (I), (II) and (III), respectively. 6-Deoxy-L-talose was isolated as a sugar component of zizyphus saponins I and III.

  酸枣仁皂苷I、II、III和枣仁皂苷B自酸枣仁中分离而得。酸枣仁皂苷I、II、III经Smith-de Mayo降解反应得到真正的皂苷元——酸枣仁苷元。通过PMR、CMR检测及应用Klyne分子旋光法测定了各皂苷中糖连接的构型，从而确定了酸枣仁皂苷I、II、III的结构分别为(I)、(II)和(III)。6-脱氧-L-太妃糖作为酸枣仁皂苷I和III的糖部分被分离出来。
• Preparation of carbohydrate isopropylidene derivatives with 2,2-dimethoxypropane in the presence of toluene-p-sulphonic acid
  作者：András Lipták、János Imre、Pál Nánási

  DOI：10.1016/s0008-6215(00)85991-1

  日期：——