1-[(tert-butoxycarbonyl)amino]-1-deoxy-3,4:5,6-di-O-isopropylidene-D-glucitol | 160284-01-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-[(tert-butoxycarbonyl)amino]-1-deoxy-3,4:5,6-di-O-isopropylidene-D-glucitol
• 英文别名: 1-(N-tert-butoxycarbonyl)amino-1-deoxy-3,4;5,6-di-O-isopropylidene-D-glucitol；tert-butyl N-[(2S)-2-[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethyl]carbamate
• CAS: 160284-01-5
• 化学式: C₁₇H₃₁NO₇
• 分子量: 361.436
• InChiKey: BCRMXKRDIIVLNC-UMSGYPCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  95.48
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-[(tert-butoxycarbonyl)amino]-1-deoxy-3,4:5,6-di-O-isopropylidene-D-glucitol 在 sodium periodate 、 甲酸 、 4-甲基苯磺酸吡啶 、 sodium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 5.25h， 生成 methyl 6-O-tert-butyldimethylsilyl-2,3,7-trideoxy-3,7-imino-4,5-O-isopropylidene-D-gluco-heptonate
  参考文献：
  名称：

  The synthesis of ester and ketone analogues of 1-deoxynojirimycin and castanospermine

  摘要：

  1-Amino-1-deoxy-D-glucitol (3) was converted into the 3,4;5,6-di-O-isopropylidene protected ammonium salt 17 which was transformed further into the trans-fused piperidine acetonides 4-8 in six steps and 23-32% overall yield. In the final step, ring closure was effected via cleavage of the N-Boc group of intermediates 27-29 with trimethylsilyl iodide: this enabled internal, face selective 1,4-addition of the free amino group to the (5,6)-alpha,beta-unsaturated carbonyl moiety. Further modification and (or) deprotection of compounds 4-8 afforded the piperidine and indolizidine imino sugars 9-12 and 14-15. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00794-1
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 1-amino-1-deoxy-3,4;5,6-di-O-isopropylidene-D-glucitol p-toluenesulfonate 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.42h， 以95%的产率得到1-[(tert-butoxycarbonyl)amino]-1-deoxy-3,4:5,6-di-O-isopropylidene-D-glucitol
  参考文献：
  名称：

  The synthesis of ester and ketone analogues of 1-deoxynojirimycin and castanospermine

  摘要：

  1-Amino-1-deoxy-D-glucitol (3) was converted into the 3,4;5,6-di-O-isopropylidene protected ammonium salt 17 which was transformed further into the trans-fused piperidine acetonides 4-8 in six steps and 23-32% overall yield. In the final step, ring closure was effected via cleavage of the N-Boc group of intermediates 27-29 with trimethylsilyl iodide: this enabled internal, face selective 1,4-addition of the free amino group to the (5,6)-alpha,beta-unsaturated carbonyl moiety. Further modification and (or) deprotection of compounds 4-8 afforded the piperidine and indolizidine imino sugars 9-12 and 14-15. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00794-1

文献信息

• The synthesis of 7-carbonyl homologues of 1-deoxynojirimycin
  作者：Amuri Kilonda、Frans Compernolle、Suzanne Toppet、Georges J. Hoornaert

  DOI：10.1016/0040-4039(94)88424-2

  日期：1994.11

  A 3,4;5,6-di-O-isopropylidene salt derivative of 1-amino-1-deoxy-D-glucitol was transformed to N-Boc protected (5,6)-α,β-unsaturated 7-carbonyl compounds. Conversion to the title piperidine products proceeded via deprotection and intramolecular 1,4-addition of the amino group.

  将1-氨基-1-脱氧-D-葡萄糖醇的3,4; 5,6-二-O-异亚丙基盐衍生物转化为N- Boc保护的（5,6）-α，β-不饱和7-羰基化合物。通过脱保护和分子内1，4-加成氨基进行向标题哌啶产物的转化。
• The Synthesis of 6-Azido and 6-Amino Analogues of 1-Deoxynojirimycin and their Conversion to Bicyclic Derivatives
  作者：Amuri Kilonda、Frans Compernolle、Koen Peeters、Gert J Joly、Suzanne Toppet、Georges J Hoornaert

  DOI：10.1016/s0040-4020(00)00020-x

  日期：2000.2

  1-Amino-1-deoxy-d-glucitol (14) was converted to the N-Boc-2,3;5,6-di-O-isopropylidene derivative 16 which was transformed further into the selectively protected 2,3-O-isopropylidene 6-azido piperidine 3. The synthesis proceeded via a double inversion at C-5 involving internal attack of 4-OH to form the 4,5-epoxide 28, and ring opening of this epoxide by 1-NH2 to generate the piperidine 3. This served

  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。
• 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。
• Synthesis of 2-azido-6-amino and 2-fluoro-6-amino analogs of 1-deoxynojirimycin
  作者：Amuri Kilonda、Frans Compernolle、Georges J. Hoornaert

  DOI：10.1021/jo00123a017

  日期：1995.9

  1-Aminoglucitol (3) was transformed into iminosugars 5-8, piperidine analogues of manno- ana glucopyranose, by using a reversed-chain strategy in which the 1-amino group of 3 is retained as the 6-substituent of the iminosugars and the ring nitrogen is derived fi om an azido group introduced at C-2 of the N-Boc-3,4:5,6-O-diisopropylidene protected derivative 9. Successive deprotection of the 5,6-diol moiety, reduction of the azido group, and displacement of 6-OH with a bromo substituent result in generation of the iminosugar synthon 4. This can be deprotected directly or following inversion at the C-2 position to afford 6-amino-1,6-dideoxymannojirimycin (5) or 2-azido- and, 2-fluoro-6-amino-1,6-dideoxynojirimycin 7 and 8.