1-[(tert-butoxycarbonyl)amino]-1-deoxy-D-glucitol | 83441-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(tert-butoxycarbonyl)amino]-1-deoxy-D-glucitol
• 英文别名: 1-<(tert-butoxycarbonyl)amino>-1-deoxy-D-glucitol；N-Boc-D-glucamine；tert-butyl N-[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamate
• CAS: 83441-72-9
• 化学式: C₁₁H₂₃NO₇
• 分子量: 281.306
• InChiKey: XKJSZQQZQQPJIM-JQCXWYLXSA-N

物化性质

• 沸点：
  568.1±50.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(tert-butoxycarbonyl)amino]-1-deoxy-D-glucitol 生成 tert-butyl N-[(2S,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]carbamate
  参考文献：
  名称：

  KINAST, G.;SCHEDEL, M.;KOEBERNICK, W.

  摘要：

  DOI：
• 作为产物：
  描述：

  D-萄糖胺 、 二碳酸二叔丁酯 以 甲醇 、 水 为溶剂， 反应 4.0h， 以96%的产率得到1-[(tert-butoxycarbonyl)amino]-1-deoxy-D-glucitol
  参考文献：
  名称：

  1-脱氧野oji霉素的6-叠氮基和6-氨基类似物的合成及其向双环衍生物的转化

  摘要：

  将1-氨基-1-脱氧-d-葡萄糖醇（14）转化为N -Boc-2,3; 5,6-二-O-异亚丙基衍生物16，其进一步转化为被选择性保护的2,3- O -异亚丙基6-叠氮基哌啶3。合成过程通过C-5的两次转化进行，其中涉及4-OH的内部侵蚀，从而形成4,5-环氧化合物28，并且该环氧化物被1-NH 2开环生成哌啶3。这是各种目标化合物（即6-叠氮基和6-氨基-1,6-二脱氧野n霉素4和5以及单环和双环衍生物）的宝贵前体6 - 12。

  DOI：

  10.1016/s0040-4020(00)00020-x

文献信息

• Novel glucose-dependent insulins
  申请人：——

  公开号：US20030186846A1

  公开（公告）日：2003-10-02

  The present invention relates to insulin derivatives having a built-in glucose sensor and a polyol moiety, capable to deliver insulin from an injected depot of an insulin derivative according to the invention as a function of the glucose concentration in the surrounding tissue.

  本发明涉及一种具有内置葡萄糖传感器和多元醇基团的胰岛素衍生物，能够根据周围组织中的葡萄糖浓度从注射的胰岛素衍生物储存库中释放胰岛素。
• Glucose-dependent insulins
  申请人：Novo Nordisk A/S

  公开号：US07317000B2

  公开（公告）日：2008-01-08

  The present invention relates to insulin derivatives having a built-in glucose sensor and a polyol moiety, capable to deliver insulin from an injected depot of an insulin derivative according to the invention as a function of the glucose concentration in the surrounding tissue.

  本发明涉及一种具有内置葡萄糖传感器和多元醇基团的胰岛素衍生物，能够根据周围组织中的葡萄糖浓度，从注射的胰岛素衍生物储存库中释放胰岛素。
• Synthesis of 6-azido and 6-amino analogues of 1-deoxynojirimycin
  作者：Amuri Kilonda、Frans Compernolle、Suzanne Toppet、Georges J. Hoornaert

  DOI：10.1039/c39940002147

  日期：——

  Selective isopropylidenation of the 2,3- and 5,6-hydroxy groups of 1-[(tert-butoxycarbonyl)amino]-1-deoxy-D-glucitol 5b led to the diacetonide 6 which was converted in seven steps to the selectively protected 6-azido compound 3, a valuable precursor of various derivatives of 6-amino-1,6-dideoxynojirimycin 4b.

  对 1-[（叔丁氧羰基）氨基]-1-脱氧-D-葡萄糖醇 5b 的 2,3- 和 5,6- 羟基进行选择性异亚丙基化，可得到二丙酮 6，再经过七个步骤转化为选择性保护的 6-叠氮化合物 3，这是 6-氨基-1,6-二脱氧尻霉素 4b 各种衍生物的重要前体。
• Development of chemically stable solid phases for the target isolation with reduced nonspecific binding proteins
  作者：Teruki Takahashi、Takaaki Shiyama、Ken Hosoya、Akito Tanaka

  DOI：10.1016/j.bmcl.2005.09.011

  日期：2006.1

  Poly(methacrylate) matrices for affinity resins were designed and synthesized based on our previous results that nonspecific protein absorption on affinity resins strongly depended on their hydrophobic property. The novel affinity resins bearing FK506 (6a, 6b) captured specific binding protein, FKBP12, with a small amount of nonspecific binding proteins. The amount of nonspecific binding proteins on 6a-6b was much reduced compared to that on commercially available poly(methacrylate) resins, Toyopearl(TM) (8), and was almost the same as that on one of the most popular resins, Affigel(TM) (9). Interestingly, 6a and 6b could isolate FKBP52 as a specific binding protein as well, although 8 and 9 could not. (c) 2005 Elsevier Ltd. All rights reserved.
• Reversible Insulin Self-Assembly under Carbohydrate Control
  作者：Thomas Hoeg-Jensen、Svend Havelund、Peter K. Nielsen、Jan Markussen

  DOI：10.1021/ja051038k

  日期：2005.5.1

  Insulin with built-in pairs of boronates and polyols can produce soluble high molecular weight self-assemblies under control by carbohydrates. The illustrated principle has potential utility for general protein and peptide protraction and controlled drug release.