methyl 2-acetamido-6-bromo-2,6-dideoxy-α-D-glucopyranoside | 87236-56-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-6-bromo-2,6-dideoxy-α-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6S)-6-(bromomethyl)-4,5-dihydroxy-2-methoxyoxan-3-yl]acetamide
• CAS: 87236-56-4
• 化学式: C₉H₁₆BrNO₅
• 分子量: 298.134
• InChiKey: WQNNDXXOGYIMQB-OKNNCHMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-6-bromo-2,6-dideoxy-α-D-glucopyranoside 在 palladium on activated charcoal 、 4 A molecular sieve 氢气 作用下， 以 甲醇 为溶剂， 生成 methyl 2-acetamido-2,6-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  一种方便的制备2-乙酰氨基-2,6-二脱氧-d-葡萄糖，一些烷基糖苷和烯丙基2-乙酰氨基-2,6-二脱氧-α-d-吡喃半乳糖苷

  摘要：

  摘要用三苯基膦和N-溴丁二酰亚胺处理2-乙酰氨基-2-脱氧-d-吡喃葡萄糖的糖苷，形成6-溴-6-脱氧衍生物。这些在钯催化剂存在下的氢解作用下，产生2-乙酰氨基-2,6-二脱氧-d-吡喃葡萄糖（N-乙酰基-d-喹啉胺）的糖苷。当苄基β-d-糖苷为起始原料时，产物为游离的N-乙酰基-d-喹啉胺。在部分苯甲酰化后，烯丙基6-溴-6-脱氧-α-和-β-糖苷被氢化三丁基锡还原为烯丙基2-乙酰氨基-3-O-苯甲酰基-2,6-二脱氧-α-和-β -d-吡喃葡萄糖苷。通过连续的三氟甲基磺酰化，苯甲酸铯置换和O-去苯甲酰化，将α端基异构体转化为烯丙基2-乙酰氨基-2,6-二脱氧-α-d-吡喃半乳糖苷（N-乙酰基-d-岩藻糖胺的α糖苷）。

  DOI：

  10.1016/0008-6215(83)84057-9
• 作为产物：
  描述：

  methyl N-acetyl-D-glucosamine 在 吡啶 、 四溴化碳 、 三苯基膦 作用下， 反应 5.0h， 以60%的产率得到methyl 2-acetamido-6-bromo-2,6-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  An Efficient Synthesis of Derivatives of 2‐Acetamido‐4‐amino‐2,4,6‐trideoxy‐D‐galactopyranose

  摘要：

  Methyl 2-acetamido-4-amino-2,4,6-trideoxy-alpha-D-galactopyranoside (10) was synthesized from D-glucosamine hydrochloride in eight steps in an overall yield of 31%. Key steps include the selective benzoylation at O-3 of methyl 2-acetamido-2,6-dideoxy-alpha-D-glucopyranoside in 89% yield and the subsequent Mitsunobu reaction using diphenylphosphoryl azide as the azide source which proceeded in 92% yield. Di- and mono-benzyloxycarbonyl derivatives of 10 were also prepared.

  DOI：

  10.1081/car-120030468

文献信息

• A convenient preparation of 2-acetamido-2,6-dideoxy-d-glucose, some of its alkyl glycosides, and allyl 2-acetamido-2,6-dideoxy-α-d-galactopyranoside
  作者：Paula J. Burger、Mina A. Nashed、Laurens Anderson

  DOI：10.1016/0008-6215(83)84057-9

  日期：1983.8

  -glycoside was the starting material, the product was free N -acetyl- d -quinovosamine. The allyl 6-bromo-6-deoxy-α- and -β-glycosides, after partial benzoylation, were reduced by tributyltin hydride to allyl 2-acetamido-3- O -benzoyl-2,6-dideoxy-α- and -β- d -glucopyranoside. The α anomer was converted into allyl 2-acetamido-2,6-dideoxy-α- d -galactopyranoside (α glycoside of N -acetyl- d -fucosamine)

  摘要用三苯基膦和N-溴丁二酰亚胺处理2-乙酰氨基-2-脱氧-d-吡喃葡萄糖的糖苷，形成6-溴-6-脱氧衍生物。这些在钯催化剂存在下的氢解作用下，产生2-乙酰氨基-2,6-二脱氧-d-吡喃葡萄糖（N-乙酰基-d-喹啉胺）的糖苷。当苄基β-d-糖苷为起始原料时，产物为游离的N-乙酰基-d-喹啉胺。在部分苯甲酰化后，烯丙基6-溴-6-脱氧-α-和-β-糖苷被氢化三丁基锡还原为烯丙基2-乙酰氨基-3-O-苯甲酰基-2,6-二脱氧-α-和-β -d-吡喃葡萄糖苷。通过连续的三氟甲基磺酰化，苯甲酸铯置换和O-去苯甲酰化，将α端基异构体转化为烯丙基2-乙酰氨基-2,6-二脱氧-α-d-吡喃半乳糖苷（N-乙酰基-d-岩藻糖胺的α糖苷）。
• Preparative routes to methyl 2-acetamido-2,6-dideoxy-α-d-glucopyranoside
  作者：Robert A. Galemmo、Derek Horton

  DOI：10.1016/0008-6215(83)84058-0

  日期：1983.8
• An Efficient Synthesis of Derivatives of 2‐Acetamido‐4‐amino‐2,4,6‐trideoxy‐<scp>D</scp>‐galactopyranose
  作者：Hong Liang、T. Bruce Grindley

  DOI：10.1081/car-120030468

  日期：2004.12.26

  Methyl 2-acetamido-4-amino-2,4,6-trideoxy-alpha-D-galactopyranoside (10) was synthesized from D-glucosamine hydrochloride in eight steps in an overall yield of 31%. Key steps include the selective benzoylation at O-3 of methyl 2-acetamido-2,6-dideoxy-alpha-D-glucopyranoside in 89% yield and the subsequent Mitsunobu reaction using diphenylphosphoryl azide as the azide source which proceeded in 92% yield. Di- and mono-benzyloxycarbonyl derivatives of 10 were also prepared.