1-O-benzyl-2,3:5,6-di-O-isopropylidene-D-mannitol | 140156-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-benzyl-2,3:5,6-di-O-isopropylidene-D-mannitol
• 英文别名: (R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-[(4S,5R)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]methanol
• CAS: 140156-32-7
• 化学式: C₁₉H₂₈O₆
• 分子量: 352.428
• InChiKey: DEXIMJMBRZEWOZ-QBPKDAKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-benzyl-2,3:5,6-di-O-isopropylidene-D-mannitol 在 palladium dihydroxide 咪唑 、 氢气 、 碘 、 sodium hydride 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 ethyl 2,6-anhydro-3-deoxy-4,5:7,8-di-isopropylidene-D-glycero-D-galacto-octonate
  参考文献：
  名称：

  A new synthesis of 2-deoxy-β-Kdo, a potent CMP-Kdo synthetase inhibitor

  摘要：

  DOI：

  10.1016/0008-6215(92)84119-d
• 作为产物：
  描述：

  2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 在 sodium tetrahydroborate 、 四丁基碘化铵 、 silver(l) oxide 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 1-O-benzyl-2,3:5,6-di-O-isopropylidene-D-mannitol
  参考文献：
  名称：

  Enantioselective Synthesis of Ethyl 4,5,7,8,9-Penta-O-acetyl-2,6-anhydro- 3-deoxy-D-erythro-L-gluca-nononate: a 2-Monodeoxygenated Derivative of `2-Keto-3-deoxy-D-glycero-D-galacto-nononic Acid'

  摘要：

  A study aimed at developing an enantioselective synthesis of the title compound 23, a 2-monodeoxy analogue of;he naturally occurring (+)-2-keto-3-deoxy-D-glycero-D-galacto-2-nononic acid (KDN),is reported. From D-mannose as starting material, the chiral 1,3-diene 10, activated by a silyloxy substituent at C(2), was prepared in six steps (Scheme I). However, the intermediates were often contaminated with varying amounts of by-products arising from overoxidation during cleavage with periodic acid. An alternative route starting from the inexpensive and readily available D-isoascorbic acid (12), though a little longer than the first, satisfactorily circumvented the purification problem and led to the desired dienes 17 in good yields (scheme2). The [Co-II(S.S)-(+)-salen]-catalyzed hetero-Diels-Alder reactions of the aforementioned dienes with ethyl glyoxylate proceeded smoothly at room temperature, giving the dihydropyrano adducts 18 in moderate yields (Scheme 3). Dihydroxylation of 18a followed by reduction of the keto function gave the desired 4,5-trans dihydroxy moiety of the KDN framework (Scheme 4, see 21). The spectroscopic data of the penta-O-acetylated 2-deoxy-KDN ethyl ester 23 were consistent with those reported for the corresponding methyl ester derived from natural KDN.

  DOI：

  10.1002/(sici)1522-2675(20000510)83:5<943::aid-hlca943>3.0.co;2-h

文献信息

• 一种艾地骨化醇中间体的制备方法及其中间体
  申请人：南京圣鼎医药科技有限公司

  公开号：CN114685553A

  公开（公告）日：2022-07-01

  本发明涉及一种艾地骨化醇中间体的制备方法及其中间体。提供一种合成艾地骨化醇中间体的路线及新颖中间体，其起始原料D‑甘露糖(D‑Mannose)易得价格便宜，巧妙利用了原料D‑甘露糖(D‑Mannose)的手性并完美转化到关键艾地骨化醇中间体环己醇三醇衍生物，避免了合成中的手性控制，各步反应条件温和，提纯较易，操作简单，收率较高，产物手性纯度高，从而经济和高效的制备艾地骨化醇中间体，极大的缩短了生产周期，降低了生产成本，适合工业化生产。
• A practical approach to regioselective O-benzylation of primary positions of polyols
  作者：Maddalena Giordano、Alfonso Iadonisi

  DOI：10.1016/j.tetlet.2013.01.023

  日期：2013.3

  Exposure of saccharide polyols to a moderate excess of benzyl bromide and DIPEA at 90 degrees C results in the regioselective O-benzylation of primary positions in moderate to good yields. The reactions can be performed without inert atmosphere and provide synthetically useful yields within a few hours. (c) 2013 Elsevier Ltd. All rights reserved.
• Enantioselective Synthesis of Ethyl 4,5,7,8,9-Penta-O-acetyl-2,6-anhydro- 3-deoxy-D-erythro-L-gluca-nononate: a 2-Monodeoxygenated Derivative of `2-Keto-3-deoxy-D-glycero-D-galacto-nononic Acid'
  作者：Xin Shen、Yu-Lin Wu、Yikang Wu

  DOI：10.1002/(sici)1522-2675(20000510)83:5<943::aid-hlca943>3.0.co;2-h

  日期：2000.5.10

  A study aimed at developing an enantioselective synthesis of the title compound 23, a 2-monodeoxy analogue of;he naturally occurring (+)-2-keto-3-deoxy-D-glycero-D-galacto-2-nononic acid (KDN),is reported. From D-mannose as starting material, the chiral 1,3-diene 10, activated by a silyloxy substituent at C(2), was prepared in six steps (Scheme I). However, the intermediates were often contaminated with varying amounts of by-products arising from overoxidation during cleavage with periodic acid. An alternative route starting from the inexpensive and readily available D-isoascorbic acid (12), though a little longer than the first, satisfactorily circumvented the purification problem and led to the desired dienes 17 in good yields (scheme2). The [Co-II(S.S)-(+)-salen]-catalyzed hetero-Diels-Alder reactions of the aforementioned dienes with ethyl glyoxylate proceeded smoothly at room temperature, giving the dihydropyrano adducts 18 in moderate yields (Scheme 3). Dihydroxylation of 18a followed by reduction of the keto function gave the desired 4,5-trans dihydroxy moiety of the KDN framework (Scheme 4, see 21). The spectroscopic data of the penta-O-acetylated 2-deoxy-KDN ethyl ester 23 were consistent with those reported for the corresponding methyl ester derived from natural KDN.
• A new synthesis of 2-deoxy-β-Kdo, a potent CMP-Kdo synthetase inhibitor
  作者：Hiroshi Ohrui、Masahiro Morita、Hiroshi Meguro

  DOI：10.1016/0008-6215(92)84119-d

  日期：1992.2