5-azido-3,6-di-O-benzyl-5-deoxy-D-glucono-1,4-lactone | 128984-73-6

• 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: 5-azido-3,6-di-O-benzyl-5-deoxy-D-glucono-1,4-lactone
• 英文别名: (3R,4R,5R)-5-[(1R)-1-azido-2-phenylmethoxyethyl]-3-hydroxy-4-phenylmethoxyoxolan-2-one
• CAS: 128984-73-6
• 化学式: C₂₀H₂₁N₃O₅
• 分子量: 383.404
• InChiKey: NONHJUCMCWXKTR-NCXUSEDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-azido-3,6-di-O-benzyl-5-deoxy-D-glucono-1,4-lactone 在 吡啶 、 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 38.5h， 生成 (2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-N-methylpyrrolidine-2-carboxamide
  参考文献：
  名称：

  Nine of 16 Stereoisomeric Polyhydroxylated Proline Amides Are Potent β-N-Acetylhexosaminidase Inhibitors

  摘要：

  All 16 stereoisomeric N-methyl 5-(hydroxymethyl)-3,4-dihydroxyproline amides have been synthesized from lactones accessible from the enantiomers of glucuronolactone. Nine stereoisomers, including all eight with a (3R)-hydroxyl configuration, are low to submicromolar inhibitors of beta-N-acetylhexosaminidases. A structural correlation between the proline amides is found with the ADMDP-acetamide analogues bearing an acetamidomethylpyrrolidine motif. The proline amides are generally more potent than their ADMDP-acetamide equivalents. beta-N-Acetylhexosaminidase inhibition by an azetidine ADMDP-acetamide analogue is compared to an azetidine carboxylic acid amide. None of the amides are good alpha-N-acetylgalactosaminidase inhibitors.

  DOI：

  10.1021/jo500157p
• 作为产物：
  描述：

  1,2-O-isopropylidene-3,6-di-O-benzyl-5-azido-5-deoxy-α-D-glucofuranose 在 溴 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 5-azido-3,6-di-O-benzyl-5-deoxy-D-glucono-1,4-lactone
  参考文献：
  名称：

  脱氧野oji霉素和野ji霉素δ-内酰胺的合成

  摘要：

  报道了从不同的偶氮呋喃糖中间体合成诺吉霉素δ-1内酰胺和脱氧诺吉霉素。

  DOI：

  10.1016/s0040-4039(00)94568-4

文献信息

• Glycosidase Inhibition by All 10 Stereoisomeric 2,5-Dideoxy-2,5-iminohexitols Prepared from the Enantiomers of Glucuronolactone
  作者：Benjamin J. Ayers、Nigel Ngo、Sarah F. Jenkinson、R. Fernando Martínez、Yousuke Shimada、Isao Adachi、Alexander C. Weymouth-Wilson、Atsushi Kato、George W. J. Fleet

  DOI：10.1021/jo301243s

  日期：2012.9.21

  glucuronolactone are excellent chirons for the synthesis of the 10 stereoisomeric 2,5-dideoxy-2,5-iminohexitols by formation of the pyrrolidine ring by nitrogen substitution at C2 and C5, with either retention or inversion of configuration; the stereochemistry at C3 may be adjusted during the synthesis to give seven stereoisomers from each enantiomer. A definitive side-by-side comparison of the glycosidase

  葡糖醛酸内酯的对映体是用于合成10个立体异构体2,5-二脱氧-2,5-亚氨基己糖醇的优秀的Chirons，通过在C2和C5处进行氮取代形成吡咯烷环，而保留或反转构型。在合成过程中，可以调节C3处的立体化学，以从每种对映异构体中产生7种立体异构体。对一组13种糖苷酶的糖苷酶抑制作用的确定性并排比较显示，这10种立体异构体中有8种对至少一种糖苷酶具有明显的抑制作用。
• Synthesis of nojirimycin derivatives
  申请人：Monsanto Company

  公开号：EP0423099A1

  公开（公告）日：1991-04-17

  Nojirimycin δ-lactam and deoxynojirimycin are each synthesized from 5,6-anhydro-3-O-benzyl-­1,2-O-isopropylidene-L-idofuranose as a divergent intermediate by a method which comprises formation of the piperidine ring by connection of nitrogen between C-1 and C-5 with inversion of configuration at C-5 to form nojirimycin δ-lactam or between C-2 and C-6 with inversion of configuration at C-2.

  Nojirimycin δ-内酰胺和 deoxynojirimycin 都是由 5,6-脱水-3-O-苄基-1,2-O-异亚丙基-L-异呋喃糖作为发散中间体合成的，合成方法包括通过在 C-1 和 C-5 之间连接氮并在 C-5 处反转构型形成哌啶环，从而形成 nojirimycin δ-内酰胺，或在 C-2 和 C-6 之间连接氮并在 C-2 处反转构型。
• 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.
• FLEET, GEORGE W. J.;CARPENTER, NEIL M.;PETURSSON, SIGTHOR;RAMSDEN, NIGEL +, TETRAHEDRON LETT., 31,(1990) N, C. 409-412
  作者：FLEET, GEORGE W. J.、CARPENTER, NEIL M.、PETURSSON, SIGTHOR、RAMSDEN, NIGEL +

  DOI：——

  日期：——
• US5200523A
  申请人：——

  公开号：US5200523A

  公开（公告）日：1993-04-06