5-Benzyloxycarbonylamino-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranose | 84036-72-6

• 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-Benzyloxycarbonylamino-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranose
• 英文别名: 5-Benzyloxycarbonylamino-5-desoxy-1,2-O-isopropyliden-α-D-glucofuranose；5-benzyloxycarbonylamino-5-deoxy-1,2-O-isopropylidene-α-D-gluco-1,4-furanose；benzyl N-[(1R)-1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl]carbamate
• CAS: 84036-72-6
• 化学式: C₁₇H₂₃NO₇
• 分子量: 353.372
• InChiKey: URFZYULCFBUJND-XLWJZTARSA-N

物化性质

• 熔点：
  144-146 °C
• 沸点：
  564.9±50.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-Benzyloxycarbonylamino-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 在 platinum(IV) oxide 、 palladium on activated charcoal Dowex (OH^(1-)) 、 二氧化硫 、 氢气 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 25.0~40.0 ℃ 、100.0 kPa 条件下， 反应 138.75h， 生成 1-脱氧野尻霉素
  参考文献：
  名称：

  全合成冯诺吉霉素

  摘要：

  诺奇霉素的全合成

  DOI：

  10.1002/hlca.19820650403
• 作为产物：
  描述：

  5-Benzyloxycarbonylamino-5-desoxy-1,2-O-isopropyliden-α-D-glucofuranuronsaeure(t-butyl)ester 在 锂硼氢 、 氯丁烷 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 5-Benzyloxycarbonylamino-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  全合成冯诺吉霉素

  摘要：

  诺奇霉素的全合成

  DOI：

  10.1002/hlca.19820650403

文献信息

• Synthesis of 8-epi-Kifunensine.
  作者：Hiroshi KAYAKIRI、Teruo OKU、Masashi HASHIMOTO

  DOI：10.1248/cpb.39.1397

  日期：——

  A synthesis of 8-epi-kifunensine (2) in optically active form was achieved starting from D-glucose via a modified double cyclization of the oxamide-hemiacetal precursor 9 with 2, 4-dimethoxybenzylamine as a key step.

  以D-葡萄糖为起始原料，通过将肟-半缩醛前体9与2,4-二甲氧基苄胺进行改良的双环化反应，实现了光学活性形式的8-表-基夫宁辛（2）的合成，这是该反应的关键步骤。
• Synthesis of 8-epi-kifunensine.
  作者：Hiroshi KAYAKIRI、Teruo OKU、Masashi HASHIMOTO

  DOI：10.1248/cpb.38.293

  日期：——

  8-epi-Kifunensine(2__-) has been synthesized from D-glucose by a route involving a double cyclization of 7__- as a key step.

  8-epi-Kifunensine(2__-) 是以 D-葡萄糖为原料，通过 7__- 的双环化作为关键步骤合成的。
• Synthesis of azepane and nojirimycin iminosugars: the Sharpless asymmetric epoxidation of d-glucose-derived allyl alcohol and highly regioselective epoxide ring opening using sodium azide
  作者：Vrushali H. Jadhav、Omprakash P. Bande、Vedavati G. Puranik、Dilip D. Dhavale

  DOI：10.1016/j.tetasy.2010.01.007

  日期：2010.2

  The Sharp less asymmetric epoxidation of D-glucose-derived ally! alcohol 4 afforded alpha- and beta-epoxides 5a and 5b in high stereoselectivity. The epoxide ring opening in 5a/5b was studied with different nucleophilic azido reagents, under various reaction conditions, and was found to be highly regioselective to give the preferential formation of 6-azido diol 6a/6b over 5-azido-diol 7a/7b. The 6-azido diol 6a/6b and 5-azido dial 7a/7b thus obtained were converted to the corresponding seven- and six-membered iminosugar, namely, azepane 1a/1b and 1-deoxy-nojirimycin 2a/2b. (C) 2010 Elsevier Ltd. All rights reserved.
• 5-Amino-5-Deoxy-1-Thioglucopyranosides-Synthesis of Thioglycoside Derivatives of Nojirimycin
  作者：Thomas Fuchss、Richard R. Schmidt

  DOI：10.1080/07328300008544110

  日期：2000.1

  N-Benzyloxycarbonyl-protected 5-amino-5-deoxyglucofuranose derivative 1 could be readily transformed into 6-O, N-carbonylidene nojirimycin 3 which afforded the corresponding piperidinosyl trichloroacetimidate 6. This compound turned out to be a versatile piperidinosyl donor. Reaction with various mercaptans as accepters in the presence of TMSOTf as catalyst gave 5-aza-1-thioglucopyranosides 7a-c, 9, and 13 which were successfully deprotected.
• KAYAKIRI, HIROSHI;OKU, TERUO;HASHIMOTO, MASASHI, CHEM. AND PHARM. BULL., 38,(1990) N, C. 293-295
  作者：KAYAKIRI, HIROSHI、OKU, TERUO、HASHIMOTO, MASASHI

  DOI：——

  日期：——