2,3,4-tri-O-benzyl-D-glucono-1,5-lactone | 158464-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzyl-D-glucono-1,5-lactone
• 英文别名: 2,3,4-tri-O-benzyl-D-glucopyranolactone；(3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-one
• CAS: 158464-67-6
• 化学式: C₂₇H₂₈O₆
• 分子量: 448.516
• InChiKey: XMZVKPUOVUMSAS-FXSWLTOZSA-N

物化性质

• 沸点：
  628.1±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-D-glucono-1,5-lactone 在 咪唑 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以115 g的产率得到(3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-iodomethyl-tetrahydro-pyran-2-one
  参考文献：
  名称：

  一种SGLT2抑制剂中间体的合成方法

  摘要：

  本发明公开了一种SGLT2抑制剂中间体的合成方法，包含以下步骤：S1、氧化：将化合物Ⅰ溶解后，添加至氧化体系后，液液分离，收集有机相A得到化合物Ⅱ；S2、脱烷基：将化合物Ⅱ添加至脱烷基体系后得反应液，液液分离，得到化合物Ⅲ；S3、碘代：将化合物Ⅲ添加至碘代体系后，液液分离，收集有机相B得到化合物Ⅳ；S4、还原：将化合物Ⅳ溶解后，添加至还原体系中，液液分离，收集有机相C得到目标产物Ⅴ；本发明的合成方法合成步骤少，工艺简单易操作；合成过程未使用到昂贵及危险的化合物，没有安全风险；总收率达到60％以上；该方法使用市购的起始物料，成本低，确保了合成路线重现性好，是适用于大规模工业生产的工艺。

  公开号：

  CN112645915A
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-glucopyranose 在 N-碘代丁二酰亚胺 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 以89%的产率得到2,3,4-tri-O-benzyl-D-glucono-1,5-lactone
  参考文献：
  名称：

  Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols

  摘要：

  A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely a-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by (3)J(C,H) coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.032

文献信息

• Organoselenium reagents in the tandem β-fragmentation-cyclization of carbohydrate anomeric alkoxy radicals
  作者：Rosa L Dorta、Cosme G Francisco、Ernesto Suárez

  DOI：10.1016/s0040-4039(00)73046-2

  日期：1994.3

  Carbohydrates possessing a suitably positioned hydroxyl group in the presence of organoselenium reagents and iodine under an argon atmosphere undergo intramolecular β-fragmentation-cyclization reaction to give aldofuranose and aldopyranose forms of carbohydrates, specifically.

  在氩气气氛下，在有机硒试剂和碘的存在下，具有适当位置羟基的碳水化合物经过分子内β片段化-环化反应，生成糖醛烷呋喃糖和醛糖吡喃糖形式。
• Direct Methylenation of Partially Benzyl-Protected Sugar Lactones by Dimethyltitanocene
  作者：Xiaoliu Li、Hiro Ohtake、Hideyo Takahashi、Shiro Ikegami

  DOI：10.1055/s-2001-18772

  日期：——

  Mono- and disaccharidic exo-methylenesugars containing an unprotected hydroxy group were conveniently prepared by the direct methylenation of the corresponding mono- and disaccharidic lactones using dimethyltitanocene.

  通过使用二甲基二茂钛对相应的单糖和二糖内酯进行直接甲基化，可以方便地制备含有未保护羟基的单糖和二糖外亚甲基糖。
• 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.
• Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols
  作者：Rie Namme、Takashi Mitsugi、Hideyo Takahashi、Moto Shiro、Shiro Ikegami

  DOI：10.1016/j.tet.2006.07.032

  日期：2006.9

  A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely a-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by (3)J(C,H) coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective. (c) 2006 Elsevier Ltd. All rights reserved.
• 一种SGLT2抑制剂中间体的合成方法
  申请人：广州安岩仁医药科技有限公司

  公开号：CN112645915A

  公开（公告）日：2021-04-13

  本发明公开了一种SGLT2抑制剂中间体的合成方法，包含以下步骤：S1、氧化：将化合物Ⅰ溶解后，添加至氧化体系后，液液分离，收集有机相A得到化合物Ⅱ；S2、脱烷基：将化合物Ⅱ添加至脱烷基体系后得反应液，液液分离，得到化合物Ⅲ；S3、碘代：将化合物Ⅲ添加至碘代体系后，液液分离，收集有机相B得到化合物Ⅳ；S4、还原：将化合物Ⅳ溶解后，添加至还原体系中，液液分离，收集有机相C得到目标产物Ⅴ；本发明的合成方法合成步骤少，工艺简单易操作；合成过程未使用到昂贵及危险的化合物，没有安全风险；总收率达到60％以上；该方法使用市购的起始物料，成本低，确保了合成路线重现性好，是适用于大规模工业生产的工艺。