2-azido-3,4-di-O-acetyl-2-deoxy-α-L-fucopyranozyl nitrate | 70717-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-3,4-di-O-acetyl-2-deoxy-α-L-fucopyranozyl nitrate
• 英文别名: 3,4-Di-O-acetyl-2-azido-2,6-didesoxy-α-L-galactopyranosylnitrat；2-azido-3,4-di-O-acetyl-2-deoxy-α-L-fucopyranosyl nitrate；3,4-Di-O-acetyl-2-azido-2-deoxy-α-L-fucopyranosyl nitrate；3,4-di-O-acetyl-2-azido-2,6-dideoxy-α-L-galactopyranosyl nitrate；2-azido-1-O-nitro-3,4-di-O-acetyl-α-L-fucose；[(2S,3R,4S,5S,6S)-4-acetyloxy-5-azido-2-methyl-6-nitrooxyoxan-3-yl] acetate
• CAS: 70717-96-3
• 化学式: C₁₀H₁₄N₄O₈
• 分子量: 318.243
• InChiKey: BHDHWVFRBCKVRT-SGZWNVLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-azido-3,4-di-O-acetyl-2-deoxy-α-L-fucopyranozyl nitrate 在 4 A molecular sieve 、 三乙基硅基三氟甲磺酸酯 、 potassium carbonate 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 4-methoxyphenyl 2-azido-3,4-di-O-acetyl-2-deoxy-α-L-fucopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the Trisaccharide Repeating Unit of the O‐Antigen Related to the EnterohemorrhagicEscherichia coliType O26:H

  摘要：

  L-Fucose was converted to the 2-azido-2-deoxy-L-fucose derivative, which together with the monosaccharide synthons prepared from L-rhamnose and D-glucosamine hydrochloride were utilized for the synthesis of the p-ethoxyphenyl glycoside of the trisaccharide repeating unit of the antigen from enterohemorrhagic Escherichia coli type O26:H.

  DOI：

  10.1081/car-120020480
• 作为产物：
  描述：

  2,6-脱水-1,5-二脱氧-L-阿拉伯-己-5-烯糖二乙酸酯 在 sodium azide 、 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以52%的产率得到2-azido-3,4-di-O-acetyl-2-deoxy-α-L-fucopyranozyl nitrate
  参考文献：
  名称：

  Synthesis of the Trisaccharide Repeating Unit of the O‐Antigen Related to the EnterohemorrhagicEscherichia coliType O26:H

  摘要：

  L-Fucose was converted to the 2-azido-2-deoxy-L-fucose derivative, which together with the monosaccharide synthons prepared from L-rhamnose and D-glucosamine hydrochloride were utilized for the synthesis of the p-ethoxyphenyl glycoside of the trisaccharide repeating unit of the antigen from enterohemorrhagic Escherichia coli type O26:H.

  DOI：

  10.1081/car-120020480

文献信息

• The synthesis ofN-acetyl-β-l-fucosamine-1-phosphate and uridine 5′-diphospho-N-acetyl-β-l-fucosamine
  作者：P. A. Illarionov、V. I. Torgov、I. Hancock、V. N. Shibaev

  DOI：10.1007/bf02494930

  日期：2000.11

  Uridine 5′-(2-acetamido-2,6-dideoxy-β-l-galactopyranosyl) diphosphate (uridine 5′-diphospho-N-acetyl-β-l-fucosamine) was synthesized. The key intermediate, 3,4-di-O-acetyl-2-azido-2,6-dideoxy-β-l-galactopyranosyl dibenzyl phosphate, was prepared by a previously unknown reaction of cesium dibenzyl phosphate with the corresponding α-glycosyl nitrate and was then converted into theN-acetylated glycosyl

  合成了尿苷 5'-（2-乙酰氨基-2,6-二脱氧-β-1-吡喃半乳糖基）二磷酸（尿苷 5'-二磷酸-N-乙酰基-β-1-岩藻糖胺）。关键中间体 3,4-di-O-acetyl-2-azido-2,6-dideoxy-β-l-galactopyranosyl dibenzyl phosphate 是通过先前未知的磷酸二苄基铯与相应的 α-糖基硝酸酯反应制备的然后通过温和的N-乙酰化和O-脱乙酰作用，通过3,4-二-O-乙酰-2-氨基-2,6-二脱氧-β-1-吡喃半乳糖基磷酸酯转化为N-乙酰化磷酸糖和核苷二磷酸糖合成步骤。
• Synthesis of glycosyl phosphates from acetylated glycosyl nitrates
  作者：Petr A. Illarionov、Vladimir I. Torgov、Ian C. Hancock、Vladimir N. Shibaev

  DOI：10.1016/s0040-4039(99)00698-x

  日期：1999.5

  Acetylated α-glycosyl nitrates were efficiently converted under mild conditions into protected β-glycosyl phosphates by treatment with cesium dibenzyl phosphate or into thermodynamically more stable α-glycosyl phosphate derivatives upon interaction with cesium diphenyl phosphate. These reactions were found to be applicable both to 2-azido-2,6-dideoxy- and 2-azido-2-deoxygalactopyranosyl nitrates as

  通过用磷酸二苄基铯处理，乙酰化的α-糖基硝酸酯在温和的条件下可以有效地转化为受保护的β-糖基磷酸酯，或者在与磷酸二苯酯铯相互作用时转化为热力学上更稳定的α-糖基磷酸酯衍生物。发现这些反应适用于2-叠氮基2，6-二脱氧-和2-叠氮基2-脱氧半乳糖吡喃糖基硝酸盐以及6-脱氧半乳糖吡喃糖基和半乳糖吡喃糖基的衍生物。
• Synthesis of ω-(methoxycarbonyl)alkyl and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides for the preparation of carbohydrate-protein conjugates
  作者：Tamio Sugawara、Kunihiko Irie、Hiroyuki Iwasawa、Takayoshi Yoshikawa、Satoshi Okuno、Hiroshi K. Watanabe、Takashi Kato、Mitsuru Shibukawa、Yukio Ito

  DOI：10.1016/s0008-6215(00)90517-2

  日期：1992.6

  Omega-(Methoxycarbonyl)alkyl glycopyranosides of D-mannose having C4, C-7, C-9, C-12, and C-15 carbon chains, L-fucose and 2-acetamido-2-deoxy-D-mannose having C-7 and C-9 carbon chains. D-xylose and 2-acetamido-2-deoxy-L-fucose having a C-9 carbon chian, and 9-(methoxycarbonyl)-3,6-dioxanoyl glycopyranosides of D-mannose. 2-acetamido-2-deoxy-D-mannose, and L-fucose were' synthesized as intermediates for coupling to human serum albumin in order to examine the effect of chain length and hydrophobicity of the spacer arm on the binding specificity of lectins. 8-(Methoxycarbonyl)octyl glycosides of beta-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-ManNAc-(1 --> 2)-alpha-D-Man, beta-D-GlcNAc-(1 --> 2)-alpha-D-Man, and their 6-O-positional isomers, beta-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-ManNAc-(1 --> 6)-alpha-D-Man, and beta-D-GlcNAc-(1 --> 6)-alpha-D-Man, were also synthesized.
• Horito, Shigeomi; Lorentzen, Jens Peter; Paulsen, Hans, Liebigs Annalen der Chemie, 1986, # 11, p. 1880 - 1890
  作者：Horito, Shigeomi、Lorentzen, Jens Peter、Paulsen, Hans

  DOI：——

  日期：——
• Azidonitration of Di-<i>O</i>-acetyl-<scp>L</scp>-fucal: X-Ray Crystal Structures of Intermediate Azidodeoxysugars and of the Bacterial Aminosugar <i>N</i>-Acetyl-<scp>L</scp>-fucosamine
  作者：Abdul-Basit Alhassan、David C. McCutcheon、Matthias Zeller、Peter Norris

  DOI：10.1080/07328303.2012.658125

  日期：2012.5.1

  The azidonitration of di-O-acetyl-L-fucal has previously been shown to be an efficient route to the bacterial aminosugar N-acetyl-L-fucosamine. Upon repeating this sequence, with updated versions of the glycal formation and amide installation steps, we have obtained X-ray crystal structures of several of the addition products, which are now reported along with the solid-state structure of N-acetyl-L-fucosamine itself.