dimethyl 2,3,4-tri-O-benzyl-β-L-idopyranosiduronate | 120567-49-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl 2,3,4-tri-O-benzyl-β-L-idopyranosiduronate
• 英文别名: methyl (2R,3S,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxane-2-carboxylate
• CAS: 120567-49-9
• 化学式: C₂₉H₃₂O₇
• 分子量: 492.569
• InChiKey: ATDWPIKETLLHRS-ZYIIXBBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 2,3,4-tri-O-benzyl-β-L-idopyranosiduronate 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 22.0h， 以100%的产率得到dimethyl β-L-idopyranosiduronate
  参考文献：
  名称：

  非对映选择性硼氢化/氧化从 5-吡喃糖苷合成 1-吡喃糖苷

  摘要：

  研究了利用 5-enopyranosides 的非对映选择性硼氢化/氧化改进 L-pyranosides 的合成。偶然发现了硼氢化的非对映选择性的独特现象。该方法成功应用于L-艾杜糖醛酸的合成。

  DOI：

  10.1055/s-2004-834889
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside 在 chromium(VI) oxide 、 硼烷四氢呋喃络合物 、 硫酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 4.17h， 生成 dimethyl 2,3,4-tri-O-benzyl-β-L-idopyranosiduronate
  参考文献：
  名称：

  非对映选择性硼氢化/氧化从 5-吡喃糖苷合成 1-吡喃糖苷

  摘要：

  研究了利用 5-enopyranosides 的非对映选择性硼氢化/氧化改进 L-pyranosides 的合成。偶然发现了硼氢化的非对映选择性的独特现象。该方法成功应用于L-艾杜糖醛酸的合成。

  DOI：

  10.1055/s-2004-834889

文献信息

• Synthesis of Protected Carbohydrate Derivatives Through Homologation of Threose and Erythrose Derivatives with Chiral .gamma.-Alkoxy Allylic Stannanes
  作者：James A. Marshall、Boris M. Seletsky、George P. Luke

  DOI：10.1021/jo00091a034

  日期：1994.6

  Additions of the gamma-alkoxy allylic stannanes (S)-1 and (R)-1 and the racemate (RS)-1 to the threose and erythrose aldehyde derivatives 6 and 15 in the presence of BF3.OEt(2) or MgBr2.OEt(2) were examined in order to establish stereochemical preferences. It was found that (S)-1 and aldehyde 6 afforded the syn,anti,syn adduct 7 in the BF3-promoted reaction, while (R)-1 and 6 gave the syn,syn,syn adduct 8 under MgBr2 conditions. Likewise, (S)-1 and aldehyde 15 yielded the syn,anti,anti adduct 16 with BF3, whereas (R)-1 and 15 led to the syn,syn,anti adduct 17 with MgBr2. The MgBr2-promoted reactions showed sufficient rate differences between the matched and mismatched stannanes to allow the use of racemic stannane (RS)-1 in just over 2-fold excess, whereupon the matched adducts 8 and 17 were favored by greater than 9:1 over the mismatched adducts. The major adducts 7, 8, 16, and 17 were converted to the hexose derivatives 21, 30/31, 34, and 39 by ozonolysis, selective deprotection, and refunctionalization. Adducts 16 and 17 were dihydroxylated with OsO4-NMO to the deoxyoctose precursors 40/41 and 42/43.
• CHIDA, NORITAKA;YAMADA, ERIKO;OGAWA, SEIICHIRO, J. CARBOHYDR. CHEM., 7,(1988) N 3, C. 555-570
  作者：CHIDA, NORITAKA、YAMADA, ERIKO、OGAWA, SEIICHIRO

  DOI：——

  日期：——
• Synthesis of<scp>l</scp>-Pyranosides from 5-Enopyranosides by Diastereoselective Hydroboration/Oxidation
  作者：Shiro Ikegami、Hideyo Takahashi、Namisa Miyama、Haruhiko Mitsuzuka

  DOI：10.1055/s-2004-834889

  日期：——

  Improved synthesis of L-pyranosides utilizing diastereoselective hydroboration/oxidation of 5-enopyranosides was investigated. A unique phenomenon in the diastereoselectivity of the hydroboration was incidentally found. The method was successfully applied to the synthesis of L-iduronic acid.

  研究了利用 5-enopyranosides 的非对映选择性硼氢化/氧化改进 L-pyranosides 的合成。偶然发现了硼氢化的非对映选择性的独特现象。该方法成功应用于L-艾杜糖醛酸的合成。
• Divergent Synthesis ofL-Sugars andL-Iminosugars fromD-Sugars
  作者：Hideyo Takahashi、Tomomi Shida、Yuko Hitomi、Yoshinori Iwai、Namisa Miyama、Kazusa Nishiyama、Daisuke Sawada、Shiro Ikegami

  DOI：10.1002/chem.200600268

  日期：2006.7.24

  AbstractAn efficient divergent synthesis of L‐sugars and L‐iminosugars from D‐sugars is described. The important intermediate, δ‐hydroxyalkoxamate, prepared from D‐glucono‐/galactono‐1,5‐lactone, was cyclized under Mitsunobu conditions to give the O‐cyclized oxime compound and the N‐cyclized lactam compound as mixtures. A more detailed investigation revealed that the appropriate protecting groups and solvents controlled the specificity for the O‐/N‐cyclization of the δ‐hydroxyalkoxamate. Suitable protection at the 6‐position of δ‐hydroxyalkoxamate, derived from D‐glucono‐1,5‐lactone, afforded the corresponding O‐alkylation product alone. Thus we succeeded in applying this to the total synthesis of L‐iduronic acid. In contrast, with both TBDMS as the protecting group and RCN as the solvent the efficient conversion of D‐glucono/galactono‐1,5‐lactone into the corresponding L‐iminosugars (L‐idonolactam and L‐altronolactam) was achieved.