Benzoic acid (2S,3S,4S,5S,6S)-2-bromomethyl-5-hydroxy-6-methoxy-4-methyl-tetrahydro-pyran-3-yl ester | 79386-70-2

• 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: Benzoic acid (2S,3S,4S,5S,6S)-2-bromomethyl-5-hydroxy-6-methoxy-4-methyl-tetrahydro-pyran-3-yl ester
• 英文别名: [(2S,3S,4S,5S,6S)-2-(bromomethyl)-5-hydroxy-6-methoxy-4-methyloxan-3-yl] benzoate
• CAS: 79386-70-2
• 化学式: C₁₅H₁₉BrO₅
• 分子量: 359.217
• InChiKey: RXWWMOFWWRIJKJ-SMCRKZLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2S,3S,4S,5S,6S)-2-bromomethyl-5-hydroxy-6-methoxy-4-methyl-tetrahydro-pyran-3-yl ester 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 正丁基锂 、 三氟化硼乙醚 、 sodium cyanoborohydride 、 potassium carbonate 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 丙醇 、 二氯甲烷 、 水 为溶剂， 反应 0.75h， 生成 (3S,4S,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-methyloct-1-en-7-yne
  参考文献：
  名称：

  Synthesis and testing of 2α-Modified 1α,25-Dihydroxyvitamin D3 analogues with a double side chain: marked cell differentiation activity

  摘要：

  The 2alpha-methyl-, 2alpha-(3-hydroxypropyl)-, and 2alpha-(3-hydroxypropoxy)-derivatives of the 'double side chain' analogue of 1alpha,25-dihydroxyvitamin D-3 were synthesized using Trost A-ring/CD-ring connective strategy. Regarding the requisite A-ring building blocks, a new, high yield and stereoselective route to the 2alpha-methyl compound starting from D-glucose was developed. All three new analogues showed potent HL-60 cancer cell differentiation activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00722-9
• 作为产物：
  描述：

  methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 barium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 为溶剂， 反应 168.58h， 生成 Benzoic acid (2S,3S,4S,5S,6S)-2-bromomethyl-5-hydroxy-6-methoxy-4-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis and testing of 2α-Modified 1α,25-Dihydroxyvitamin D3 analogues with a double side chain: marked cell differentiation activity

  摘要：

  The 2alpha-methyl-, 2alpha-(3-hydroxypropyl)-, and 2alpha-(3-hydroxypropoxy)-derivatives of the 'double side chain' analogue of 1alpha,25-dihydroxyvitamin D-3 were synthesized using Trost A-ring/CD-ring connective strategy. Regarding the requisite A-ring building blocks, a new, high yield and stereoselective route to the 2alpha-methyl compound starting from D-glucose was developed. All three new analogues showed potent HL-60 cancer cell differentiation activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00722-9

文献信息

• Revision of the assignment of relative stereochemistry in sibirosamine: synthesis of methyl n-tosyl α-d-disirosaminopyranoside
  作者：Kathlyn A. Parker、Robert E. Babine

  DOI：10.1016/s0040-4039(00)86735-0

  日期：1982.1
• Synthesis and testing of 2α-Modified 1α,25-Dihydroxyvitamin D3 analogues with a double side chain: marked cell differentiation activity
  作者：Yoshitomo Suhara、Atsushi Kittaka、Seishi Kishimoto、Martin J. Calverley、Toshie Fujishima、Nozomi Saito、Takayuki Sugiura、Keizo Waku、Hiroaki Takayama

  DOI：10.1016/s0960-894x(02)00722-9

  日期：2002.11

  The 2alpha-methyl-, 2alpha-(3-hydroxypropyl)-, and 2alpha-(3-hydroxypropoxy)-derivatives of the 'double side chain' analogue of 1alpha,25-dihydroxyvitamin D-3 were synthesized using Trost A-ring/CD-ring connective strategy. Regarding the requisite A-ring building blocks, a new, high yield and stereoselective route to the 2alpha-methyl compound starting from D-glucose was developed. All three new analogues showed potent HL-60 cancer cell differentiation activity. (C) 2002 Elsevier Science Ltd. All rights reserved.