1,2-O-Isopropyliden-L-glucuron

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 1,2-O-Isopropyliden-L-glucuron
• 英文别名: 1,2-O-isopropylidene-α-L-glucurono-3,6-lactone；(1R,2S,6S,8S,9R)-9-hydroxy-4,4-dimethyl-3,5,7,11-tetraoxatricyclo[6.3.0.02,6]undecan-10-one
• 化学式: C₉H₁₂O₆
• 分子量: 216.191
• InChiKey: BDBGJSXZKMTMGP-VGNSZIIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  1,2-O-Isopropyliden-L-glucuron 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.58h， 以60%的产率得到1,2-O-isopropylidene-α-L-glucofuranose
  参考文献：
  名称：

  Large scale synthesis of the acetonides of l-glucuronolactone and of l-glucose: easy access to l-sugar chirons

  摘要：

  1,2-O-Isopropylidene-alpha-L-glucurono-3,6-lactone may be synthesized on a 100-200 g scale from cheaply available D-glucoheptonolactone in an overall yield of 94% in four steps Via L-glucuronolactone. Subsequent elaboration to L-glucose, diacetone-L-glucose (1,2:5,6-di-O-isopropylidene-alpha-L-glucofuranose), and monoacetone-L-glucose (1,2-O-isopropylidene-alpha-L-glucofuranose) allows easy access to a range of L-sugar chirons. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.124
• 作为产物：
  描述：

  D-glycero-D-galacto-heptono-1,4-lactone 在 盐酸 、 硫酸 、 苯甲醛 作用下， 以 水 为溶剂， 反应 7.0h， 生成 1,2-O-Isopropyliden-L-glucuron
  参考文献：
  名称：

  Design and synthesis by click triazole formation of paclitaxel mimics with simplified core and side-chain structures

  摘要：

  A library of paclitaxel (taxol) mimics was obtained by a straightforward strategy involving rational design and an efficient synthesis of a simplified taxane core substitute, together with a click-chemistry combinatorial search for phenylisoserine side-chain surrogates. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.081

文献信息

• Scalable Syntheses of Both Enantiomers of DNJNAc and DGJNAc from Glucuronolactone: The Effect of N-Alkylation on Hexosaminidase Inhibition
  作者：Andreas F. G. Glawar、Daniel Best、Benjamin J. Ayers、Saori Miyauchi、Shinpei Nakagawa、Matilde Aguilar-Moncayo、José M. García Fernández、Carmen Ortiz Mellet、Elizabeth V. Crabtree、Terry D. Butters、Francis X. Wilson、Atsushi Kato、George W. J. Fleet

  DOI：10.1002/chem.201200110

  日期：2012.7.23

  The efficient scalable syntheses of 2‐acetamido‐1,2‐dideoxy‐D‐galacto‐nojirimycin (DGJNAc) and 2‐acetamido‐1,2‐dideoxy‐D‐gluco‐nojirimycin (DNJNAc) from D‐glucuronolactone, as well as of their enantiomers from L‐glucuronolactone, are reported. The evaluation of both enantiomers of DNJNAc and DGJNAc, along with their N‐alkyl derivatives, as glycosidase inhibitors showed that DGJNAc and its N‐alkyl derivatives

  2-乙酰氨基-1,2-双脱氧-D-半乳糖-野尻霉素（DGJNAc）和2-乙酰氨基-1,2-双脱氧-D-葡萄糖-野尻霉素（DNJNAc ）的高效可扩展合成，以及据报道，它们的对映异构体来自L-葡糖醛酸内酯。DNJNAc 和 DGJNAc 的两种对映异构体及其N-烷基衍生物作为糖苷酶抑制剂的评估表明，DGJNAc 及其N-烷基衍生物都是 α-GalNAcase 的抑制剂，但没有一种差向异构 DNJNAc 衍生物抑制这种酶。相比之下，DGJNAc 和 DNJNAc 以及它们的烷基衍生物都是 β-GlcNAcases 和 β-GalNAcases 的有效抑制剂。两种L-对映异构体均未显示出对所测试的任何酶的任何显着抑制。通过对溶酶体酶抑制的游离寡糖分析，体外抑制与细胞数据的相关性揭示了以下结构-性质关系：疏水侧链优先促进亚氨基糖在细胞内接近那些具有更多亲水性的抑制剂- 链特征。
• Looking glass inhibitors: scalable syntheses of DNJ, DMDP, and (3R)-3-hydroxy-l-bulgecinine from d-glucuronolactone and of l-DNJ, l-DMDP, and (3S)-3-hydroxy-d-bulgecinine from l-glucuronolactone. DMDP inhibits β-glucosidases and β-galactosidases whereas l-DMDP is a potent and specific inhibitor of α-glucosidases
  作者：Daniel Best、Chen Wang、Alexander C. Weymouth-Wilson、Robert A. Clarkson、Francis X. Wilson、Robert J. Nash、Saori Miyauchi、Atsushi Kato、George W.J. Fleet

  DOI：10.1016/j.tetasy.2010.01.017

  日期：2010.3

  A convenient large-scale synthesis of 1-deoxynojirimyin (DNJ) from D-glucuronolactone involves introduction of azide at C-5 with retention of configuration to give 5-azido-5-deoxy-1,2-O-isopropylidene-alpha-D-glucofuranose as a key intermediate in an overall yield of up to 72%; the same intermediate can be transformed into DMDP (2R,3R,4R,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol] and (3R)-3-hydroxy-L-bulgecinine [(2S,3R,4R,5R)-3,4-dihydroxy-5-hydroxymethyl-L-proline]. L-Glucuronolactone, a readily available L-sugar chiron, may similarly be used to access the enantiomers L-DNJ, L-DMDP, and (3S)-3-hydroxy-D-bulgecinine. A comparison of glycosidase inhibition by DMDP (an inhibitor of beta-glucosidases and beta-galactosidases) and L-DMDP (a potent and specific alpha-glucosidase inhibitor) with the corresponding enantiomeric hydroxybulgecinines is reported; DMDP and (3R)-3-hydroxy-L-bulgecinine show weak inhibition of glycogen phosphorylase. (C) 2010 Elsevier Ltd. All rights reserved.