3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-carbonate | 16895-86-6

• 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: 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-carbonate
• 英文别名: (4R)-4-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1,3-dioxolan-2-one
• CAS: 16895-86-6
• 化学式: C₁₇H₂₀O₇
• 分子量: 336.342
• InChiKey: GNEHYGCVTDFRPW-UXXRCYHCSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  493.3±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-carbonate 在 palladium dihydroxide 、 Dowex 50W-X₈ resin (H⁺ form) 、 sodium methylate 、 三氟乙酸 吡啶 、 甲醇 、 sodium tetrahydroborate 、 sodium azide 、 水 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.33h， 生成 1-脱氧甘露伊霉素
  参考文献：
  名称：

  D-葡萄糖合成脱氧甘露糖霉素，fagomine和2r，5r-二羟基甲基-3r，4r-二羟基吡咯烷的对映体特异性合成

  摘要：

  易于从D-葡萄糖获得的甲基2-叠氮基-3-O-苄基-2-脱氧-α-D-甘露呋喃糖苷（4）是脱氧甘露糖霉素[1,5-dideoxy-1， 5-亚氨基-D-甘露糖醇]（l），花青碱[1,2,5-三苯氧基-1,5-亚氨基-D-阿拉伯己糖醇]（2）和2R，5R-二羟基甲基-3R，4R-二羟基吡咯烷（3 ）; 这些合成建立了（2）和（3）的绝对构型。

  DOI：

  10.1016/s0040-4039(00)99073-7
• 作为产物：
  描述：

  溴甲苯 在 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-carbonate
  参考文献：
  名称：

  Chemoenzymatic synthesis of C8-modified sialic acids and related α2–3- and α2–6-linked sialosides

  摘要：

  Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized from corresponding 5-O-modified six-carbon monosaccharides and pyruvate using a sialic acid aldolase cloned from Pasteurella multocida strain P-1059 ( PmNanA). In addition, alpha 2-3- and alpha 2-6-linked sialyltrisaccharides containing Neu5Ac8Me and Kdn8Deoxy were also synthesized using a one-pot multienzyme approach. The strategy reported here provides an efficient approach to produce glycans containing various C8-modified sialic acids for biological evaluations. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.083

文献信息

• Jarosz; Szewczyk, Polish Journal of Chemistry, 2000, vol. 74, # 8, p. 1115 - 1122
  作者：Jarosz、Szewczyk

  DOI：——

  日期：——
• Synthesis of 1-(3-Azido-2,3-Dideoxy-Beta-D-Ribo-Hexofuranosyl)Thymine
  作者：Merrick R. Almond、Gregory T. Lowen、Gary E. Martin、Janet L. Rideout

  DOI：10.1080/07328319308018561

  日期：1993.11

  The nucleoside derivative 1-(3-azido-2,3-dideoxy-beta-D-ribo-hexofuranosyl)thymine has been synthesized from 3-O-benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose-5,6-carbonate in an overall yield of 16%. The key step in the synthesis involves the selective deacetylation of a nucleoside derivative having a cyclic carbonate moiety.
• Methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mamnofuranoside as a divergent intermediate for the synthesis of polyhydroxylated piperidines and pyrrolidines: synthesis of 2,5-dideoxy-2,5-imino-D-mannitol [2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine]
  作者：George W.J. Fleet、Paul W. Smith

  DOI：10.1016/s0040-4020(01)90034-1

  日期：1987.1
• Enantiospecific syntheses of deoxymannojirimycin, fagomine and 2r,5r-dihydroxymethyl-3r,4r-dihydroxypyrrolidine from D-glucose
  作者：George W.J. Fleet、Paul W. Smith

  DOI：10.1016/s0040-4039(00)99073-7

  日期：1985.1

  Methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mannofuranoside (4), readily available from D-glucose, is a common intermediate in the enantiospecific syntheses of deoxymannojirimycin [1,5-dideoxy-1,5-imino-D-mannitol](l), fagomine [1,2,5-trideoxy-1,5-imino-D- arabino hexitol] (2) and 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine (3); these syntheses establish the absolute configurations of (2) and (3).

  易于从D-葡萄糖获得的甲基2-叠氮基-3-O-苄基-2-脱氧-α-D-甘露呋喃糖苷（4）是脱氧甘露糖霉素[1,5-dideoxy-1， 5-亚氨基-D-甘露糖醇]（l），花青碱[1,2,5-三苯氧基-1,5-亚氨基-D-阿拉伯己糖醇]（2）和2R，5R-二羟基甲基-3R，4R-二羟基吡咯烷（3 ）; 这些合成建立了（2）和（3）的绝对构型。
• Chemoenzymatic synthesis of C8-modified sialic acids and related α2–3- and α2–6-linked sialosides
  作者：Hai Yu、Hongzhi Cao、Vinod Kumar Tiwari、Yanhong Li、Xi Chen

  DOI：10.1016/j.bmcl.2011.04.083

  日期：2011.9

  Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized from corresponding 5-O-modified six-carbon monosaccharides and pyruvate using a sialic acid aldolase cloned from Pasteurella multocida strain P-1059 ( PmNanA). In addition, alpha 2-3- and alpha 2-6-linked sialyltrisaccharides containing Neu5Ac8Me and Kdn8Deoxy were also synthesized using a one-pot multienzyme approach. The strategy reported here provides an efficient approach to produce glycans containing various C8-modified sialic acids for biological evaluations. (C) 2011 Elsevier Ltd. All rights reserved.

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