methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside | 118068-39-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside
• 英文别名: (2S,3S,4R,5S,6S)-2-(iodomethyl)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 118068-39-6
• 化学式: C₂₁H₂₅IO₅
• 分子量: 484.331
• InChiKey: GHZVXYINUSPEPM-XKRYSZRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside 在 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 吡啶 、 甲苯 为溶剂， 反应 6.25h， 生成 2L-(2,3/4)-2-O-acetyl-3,4-di-O-benzyl-2,3,4-trihydroxy-5-cyclohexen-1-one
  参考文献：
  名称：

  通过催化费里尔重排从碳水化合物合成光学活性取代的环己酮

  摘要：

  发现在室温下，在中性溶剂系统中，使用催化量的各种汞 (II) 盐可以有效地将 hex-5-enopyranosides 转化为取代的环己酮（Ferrier 重排）。在测试的汞 (II) 盐中，三氟乙酸汞 (II) 显示出最高的活性。使用该方法从 hex-5-enopyranosides 制备了四种光学活性环己烯酮。

  DOI：

  10.1246/bcsj.64.2118
• 作为产物：
  描述：

  (4aR,6S,7S,8S,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 在 咪唑 、 氢氧化钾 、 碘 、 三苯基膦 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 6.25h， 生成 methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside
  参考文献：
  名称：

  Synthesis of A Novel Sialyl Lewis X Analogue Containing A Pyrrolidine in Place ofN-Acetyl Glucosamine

  摘要：

  The synthesis of the new sialyl Lewis X analogue, 4-O-(alpha-L-fucopyranosyl)-3-O-(3-O-sodium sulfonato-beta-D-galactopyranosyl)-(2S,3R, 4R)-2-ethyl-3,4-dihydroxypyrrolidine 2 has been achieved. The N-acetyl glucosamine unit of natural Lewis X has been replaced by a rigid 3R/4R-dihydroxylated pyrrolidine 12. This one has been synthezised from the methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-alpha-D-altropyranoside sugar precursor 10 using the Ganem/Bernotas one-pot elimination-reductive amination ring contraction reaction. The (2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine 12 obtained was subsequently regioselectively glycosylated, using 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl fluoride and 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl bromide as glycosyl donors. Disaccharide containing pyrrolidine 21 was finally transformed into the target O-sulfated analog 2, after regioselective sulfation and usual deprotection.

  DOI：

  10.1080/07328300008544095

文献信息

• Synthesis of 2-Acetoxy-4-formylphenyl 2,3-Di-<i>O</i>-acetyl-6-deoxy-β-D-arabino-5-hexulofuranoside, Structure Confirmation of the Anomeric Configuration of Antibiotic Hygromycin A
  作者：Noritaka Chida、Masami Ohtsuka、Seiichiro Ogawa

  DOI：10.1246/cl.1988.969

  日期：1988.6.5

  2-Acetoxy-4-formylphenyl 2,3-di-O-acetyl-6-deoxy-β-D-arabino-5-hexulofuranoside, one of the degradation products of antibiotic hygromycin A, was synthesized. The present study confirmed the anomeric configuration of the antibiotic to be “β”.

  合成了 2-Acetoxy-4-formylphenyl 2,3-di-O-acetyl-6-deoxy-β-D-arabino-5-hexulofuranoside，它是抗生素潮霉素 A 的降解产物之一。本研究证实抗生素的异头构型为“β”。
• Total synthesis of antibiotic hygromycin A
  作者：Noritaka Chida、Masami Ohtsuka、Keiichi Nakazawa、Seiichiro Ogawa

  DOI：10.1021/jo00009a009

  日期：1991.4

  The first total synthesis of the antibiotic (-)-hygromycin A (1) has been achieved by a coupling reaction of the sugar moiety (2) and the cyclitol moiety (3). Both components were synthesized in homochiral forms starting from D-glucose. This synthesis fully confirmed the unique structure of 1, which is much different from other usual aminocyclitol antibiotics.
• CHIDA, NORITAKA;OHTSUKA, MASAMI;NAKAZAWA, KEIICHI;OGAWA, SEIICHIRO, J. ORG. CHEM., 56,(1991) N, C. 2976-2983
  作者：CHIDA, NORITAKA、OHTSUKA, MASAMI、NAKAZAWA, KEIICHI、OGAWA, SEIICHIRO

  DOI：——

  日期：——
• CHIDA, NORITAKA;OHTSUKA, MASAMI;OGAWA, SEIICHIRO, CHEM. LETT.,(1988) N 6, 969-972
  作者：CHIDA, NORITAKA、OHTSUKA, MASAMI、OGAWA, SEIICHIRO

  DOI：——

  日期：——