methyl 3,4-di-O-acetyl-6-S-acetyl-2-benzamido-2-deoxy-6-thio-α-D-glucopyranoside | 153527-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-acetyl-6-S-acetyl-2-benzamido-2-deoxy-6-thio-α-D-glucopyranoside
• 英文别名: [(2S,3S,4R,5R,6S)-4-acetyloxy-2-(acetylsulfanylmethyl)-5-benzamido-6-methoxyoxan-3-yl] acetate
• CAS: 153527-38-9
• 化学式: C₂₀H₂₅NO₈S
• 分子量: 439.486
• InChiKey: QUNKGTDPHXTZGX-VBEQINLCSA-N

物化性质

• 沸点：
  602.8±55.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 3,4-di-O-acetyl-6-S-acetyl-2-benzamido-2-deoxy-6-thio-α-D-glucopyranoside 在 磺酰氯 、 4 A molecular sieve 、 双氧水 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 16.0h， 生成 methyl 3,4-di-O-acetyl-2-benzamido-2,6-dideoxy-α-D-glucopyranoside-6-N-butylsulfonamide
  参考文献：
  名称：

  New N-alkylsulfonamides and alkyl sulfonates derived from 6-C-sulfosugars

  摘要：

  Protected 6-C-sulfosugars have been transformed into alkyl sulfonates and N-alkylsulfonamides, including a pseudo-disaccharide with a 6 to 6'-sulfonamide linkage. The method involves the oxidation of 6-thioacetate sugar derivatives to 6-C-sulfosugars, and their transformation into sulfonyl chlorides using SO2O2 in anhydrous CH2O2 followed by in situ coupling with nucleophiles in the presence of an excess of base. Sulfonylation through phase-transfer conditions has proved to be suitable for the synthesis of the pseudo-disaccharide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00874-8
• 作为产物：
  描述：

  Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-5-benzoylamino-6-methoxy-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester 、 钠硫代乙酸盐 以 丁酮 为溶剂， 反应 4.0h， 以90%的产率得到methyl 3,4-di-O-acetyl-6-S-acetyl-2-benzamido-2-deoxy-6-thio-α-D-glucopyranoside
  参考文献：
  名称：

  甲基2-氨基-2,6-二脱氧-α-d-吡喃葡萄糖苷-6-磺酸的合成及晶体结构

  摘要：

  摘要通过甲基3,4-二-O-乙酰基-6-S-乙酰基-2-苯甲酰胺基-2的氧化反应制得2-氨基-2-6-二脱氧-α-d-吡喃葡萄糖苷-磺酸（8） -在乙酸中用过氧化氢与-deoxy-6-thio-α-d-吡喃葡萄糖苷，然后用氢氧化钠水溶液进行N-和O-脱酰。化合物8也通过对3,4-二-O-乙酰基-6-S-乙酰基-2-脱氧-2 [（2,2-二甲氧基羰基-乙烯基）氨基] -6-硫代-α-d甲基进行氧化制得。 -吡喃葡萄糖苷，然后用Amberlite IR-120（H +）树脂脱乙酰化。对结晶为二水合物的8进行X射线分析。

  DOI：

  10.1016/0008-6215(93)84112-j

文献信息

• Synthesis and crystal structure of methyl 2-amino-2,6-dideoxy-α-d-glucopyranoside-6-sulfonic acid
  作者：José G. Fernández-Bolanos、Joaquín Morales、Salud García、M. Jesús Diánez、M. Dolores Estrada、Amparo López-Castro、Simeón Pérez

  DOI：10.1016/0008-6215(93)84112-j

  日期：1993.10

  Abstract Methyl 2-amino-2-6-dideoxy-α- d -glucopyranoside-sulfonic acid (8) was prepared by oxidation of methyl 3,4-di-O-acetyl-6-S-acetyl-2-benzamido-2-deoxy-6-thio-α- d -glucopyranoside with hydrogen peroxide in acetic acid followed by N- and O-deacylation with aqueous sodium hydroxide. Compound 8 was also obtained by oxudation of methyl 3,4-di-O-acetyl-6-S-acetyl-2-deoxy-2[(2,2-dimethoxycarbonyl-vinyl)

  摘要通过甲基3,4-二-O-乙酰基-6-S-乙酰基-2-苯甲酰胺基-2的氧化反应制得2-氨基-2-6-二脱氧-α-d-吡喃葡萄糖苷-磺酸（8） -在乙酸中用过氧化氢与-deoxy-6-thio-α-d-吡喃葡萄糖苷，然后用氢氧化钠水溶液进行N-和O-脱酰。化合物8也通过对3,4-二-O-乙酰基-6-S-乙酰基-2-脱氧-2 [（2,2-二甲氧基羰基-乙烯基）氨基] -6-硫代-α-d甲基进行氧化制得。 -吡喃葡萄糖苷，然后用Amberlite IR-120（H +）树脂脱乙酰化。对结晶为二水合物的8进行X射线分析。
• New N-alkylsulfonamides and alkyl sulfonates derived from 6-C-sulfosugars
  作者：Vı́ctor Ulgar、Inés Maya、José Fuentes、José G Fernández-Bolaños

  DOI：10.1016/s0040-4020(02)00874-8

  日期：2002.9

  Protected 6-C-sulfosugars have been transformed into alkyl sulfonates and N-alkylsulfonamides, including a pseudo-disaccharide with a 6 to 6'-sulfonamide linkage. The method involves the oxidation of 6-thioacetate sugar derivatives to 6-C-sulfosugars, and their transformation into sulfonyl chlorides using SO2O2 in anhydrous CH2O2 followed by in situ coupling with nucleophiles in the presence of an excess of base. Sulfonylation through phase-transfer conditions has proved to be suitable for the synthesis of the pseudo-disaccharide. (C) 2002 Elsevier Science Ltd. All rights reserved.