methyl 2-acetamido-2,6-dideoxy-α-D-glucopyranoside | 50286-18-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-2,6-dideoxy-α-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-2-methoxy-6-methyloxan-3-yl]acetamide
• CAS: 50286-18-5
• 化学式: C₉H₁₇NO₅
• 分子量: 219.238
• InChiKey: OHKVWIJIIUVQDR-BTZCVUIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 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-2,6-dideoxy-α-D-glucopyranoside 在 palladium on activated charcoal 吡啶 、 叠氮磷酸二苯酯 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 49.5h， 生成 methyl 2,4-diacetamido-2,4,6-trideoxy-α-D-galactopyranoside
  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
• 作为产物：
  描述：

  D-GlcNAc 在 Raney nickel W-2 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 Dowex 50W-X₈ cation exchange resin 、 氢气 、 三乙胺 、 barium carbonate 、 zinc(II) chloride 作用下， 以 甲醇 、 四氯化碳 为溶剂， 反应 71.5h， 生成 methyl 2-acetamido-2,6-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Preparative routes to methyl 2-acetamido-2,6-dideoxy-α-d-glucopyranoside

  摘要：

  DOI：

  10.1016/0008-6215(83)84058-0

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）。
• Synthesis of methyl 2-acetamido-2,6-dideoxy-α- and β-d-xylo-hexopyranosid-4-ulose, a keto sugar which misled the analytical chemists
  作者：Sabine Borowski、Dirk Michalik、Helmut Reinke、Christian Vogel、Anna Hanuszkiewicz、Katarzyna A. Duda、Otto Holst

  DOI：10.1016/j.carres.2008.02.001

  日期：2008.5

  To understand the contradictory results on the structure of the lipopolysaccharide isolated from a Yersinia enterocolitica O:3, both anomers of methyl 2-acetamido-2,6-dideoxy-D-xylo-hexopyranosid-4-ulose were prepared. The key steps of the synthetic pathway were the selective acetylation of the methyl 2-acetamido-2,6-dideoxy-alpha,beta-D-glucopyranosides, the oxidation of the 4-position to form the keto-sugars, and deacetylation to provide the target compound. Surprisingly, the last step was accompanied by a disproportionation to give methyl 2-acetamido-2,6-dideoxy-alpha- and beta-D-glucopyranosides and N-(5-hydroxy-6-methyl-4-oxo-4H-pyran-3-yl)acetamide as side-products. (c) 2008 Elsevier Ltd. All rights reserved.
• Roy, Abhijit; Ray, Asim K.; Mukherjee, Atryee, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 1165 - 1167
  作者：Roy, Abhijit、Ray, Asim K.、Mukherjee, Atryee、Roy, Nirmolendu

  DOI：——

  日期：——
• ROY, ABHIJIT;RAY, ASIM K.;MUKHERJEE, ATRYEE;ROY, NIRMOLENDU, INDIAN J. CHEM. B., 26,(1987) N2, C. 1165-1167
  作者：ROY, ABHIJIT、RAY, ASIM K.、MUKHERJEE, ATRYEE、ROY, NIRMOLENDU

  DOI：——

  日期：——
• 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.