Benzyl 2,6-Dideoxy-α-D-arabino-hexopyranoside | 75810-07-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzyl 2,6-Dideoxy-α-D-arabino-hexopyranoside
• 英文别名: Benzyl-2,6-didesoxy-α-D-arabino-hexopyranosid；benzyl 2,6-dideoxy-α-D-glucopyranoside；(2R,3S,4R,6S)-2-methyl-6-phenylmethoxyoxane-3,4-diol
• CAS: 75810-07-0
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: HKVKPOJNFRNEJA-FOUMNBMASA-N

物化性质

• 沸点：
  387.8±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Benzyl 2,6-Dideoxy-α-D-arabino-hexopyranoside 在 palladium on activated charcoal 吡啶 、 2,3,5-三甲基吡啶 、 氢氧化钾 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 四丁基溴化铵 、 氢气 、 溴 、 三正丁基氢锡 、 silver trifluoromethanesulfonate 、 溶剂黄146 、 barium carbonate 作用下， 以 硝基甲烷 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 197.0h， 生成 Bamflalactone Triacetate
  参考文献：
  名称：

  Preparation of .alpha.- and .beta.-linked disaccharides of 2,6-dideoxy-D-arabino-hexose. Synthesis of bamflalactone

  摘要：

  DOI：

  10.1021/jo00191a006
• 作为产物：
  描述：

  2-Deoxy-D-glucose 在 吡啶 、 四溴化碳 、 Dowex 50W-X₈ (H⁺ form) 、 三正丁基氢锡 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 44.0h， 生成 Benzyl 2,6-Dideoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Unusual stereoselectivity in sialic acid aldolase-catalyzed aldol condensations: synthesis of both enantiomers of high-carbon monosaccharides

  摘要：

  An inversion of stereoselectivity in aldol condensations catalyzed by sialic acid aldolase (from Escherichia coli, Shinko American Inc.) was observed when L-mannose, 6-deoxy-L-mannose, L-talose, 2-deoxy-L-glucose, 2-deoxy-L-rhamnose, N-acetyl-L-mannosamine, D-gulose, D-arabinose, and 2-azido-2-deoxy-L-mannose were used as acceptor substrates. In all substrates tested, except the last three, a complete inversion of stereoselectivity was observed; i.e., the C-nucleophile of pyruvate attacks the re face of the acceptor carbonyl instead of the si face as in the normal case for the enantiomeric substrates. Examination of the product distribution during the course of enzymatic reactions indicates that the stereoselectivity is thermodynamically controlled in nature; i.e., attack on the re face would take place if the resulting product would be more stable than the one from the si face attack. Both enantiomers of several high-carbon monosaccharides are now accessible via the aldolase reactions. A new practical procedure has also been developed for the preparation of the aldolase products where unreacted pyruvate (usually used in 7-fold excess to drive the reaction) is decomposed with pyruvate decarboxylase to simplify product isolation.

  DOI：

  10.1021/ja00052a008

文献信息

• 2-bromo-2-deoxy sugars as starting materials for the synthesis of α- or β-glycosides of 2-deoxy sugars
  作者：Klaus Bock、Inge Lundt、Christian Pedersen

  DOI：10.1016/0008-6215(84)85275-1

  日期：1984.7

  -acetyl-2,6-dibromo-2,6-dideoxy-α- d -gluco- ( 1 ) and - d -manno-pyranosyl bromide ( 18 ) gave, in glycosidation reactions, 1,2- trans -glycosides. β- d -Glycosides were formed as the main products from 1 in moderate yields, whereas 18 gave α- d -glycosides exclusively and in high yields. The 2,6-dibromo-2,6-dideoxy-β- d -glucosides were converted into the 2,6-dideoxy-β- d -glycosides by treatment with

  摘要3,4-二-O-乙酰基-2,6-二溴-2,6-二脱氧-α-d-葡萄糖-（1）和-d-甘露聚糖-吡喃糖基溴（18）在糖苷化反应中得到1 ，2-反式-糖苷。β-d-糖苷是从1中以中等收率形成的主要产物，而18则以高收率专门提供了α-d-糖苷。通过用三丁基锡烷处理并从2,6-二溴中除去溴原子，将2,6-二溴-2,6-二脱氧-β-d-葡萄糖苷转化为2,6-二脱氧-β-d-糖苷。 -2，6-二脱氧-α-d-甘露糖苷也可通过催化氢解作用得到2，6-二脱氧-α-d-糖苷。
• Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 17: Synthesis and opening reactions of cis- and trans-oxides derived from (2S,6R)-2-benzyloxy-6-methyl-3,6-dihydro-2H-pyran, (2R,6R)- and (2S,6R)-2-methoxy-6-methyl-5,6-dihydro-2H-pyran
  作者：Paolo Crotti、Valeria Di Bussolo、Lucilla Favero、Franco Macchia、Mauro Pineschi

  DOI：10.1016/s0040-4020(02)00578-1

  日期：2002.7

  The regiochemical behavior of the title deoxy anhydrosugars, prepared in an enantioselective way starting from methyl α-d-glucopyranoside, was examined in opening reactions, both under standard and chelating conditions. The results clearly indicate the influence of the reaction conditions and the importance of the relative orientation of the methyl group with respect to the oxirane ring on the regiochemical

  在标准和螯合条件下，在开放反应中检查了以对映选择性方式从甲基α-d-吡喃葡萄糖苷开始制备的标题脱氧脱水糖的区域化学行为。结果清楚地表明了反应条件的影响以及甲基相对于环氧乙烷环的相对取向的重要性对这些环氧化物的区域化学结果的影响。在某些情况下，可以获得区域选择性的有效反转。
• Glycosidsynthesen nach dem <i>N</i> ‐Iodsuccinimid‐Verfahren mit <scp>L</scp> ‐Olivomycal. Darstellungen von ED‐Disaccharidglycosiden des Chromomycins A ₃
  作者：Joachim Thiem、Jürgen Elvers

  DOI：10.1002/cber.19801130919

  日期：1980.9

  AbstractMit unterschiedlichen Alkoholen reagiert 4‐O‐Acetyl‐L‐olivomycal (2) nach dem N‐Iodsuccinimid‐Verfahren glatt zu den α‐Glycosiden 3–6 der 2‐Iod‐L‐olivomycose. Mit N‐Brom‐ bzw. N‐Iodsuccinimid wird aus 2 und dem 2‐Desoxy‐D‐arabino‐Derivat 1 das 2′‐Brom‐Derivat 7 in geringer bzw. die 2′‐Iod‐Verbindung 8 in guter Ausbeute gewonnen. Die bromierende Benzylidenring‐öffnung von 8 gibt das labile 6‐Brom‐ 2′‐iod‐disaccharid 9, aus dem reduktiv das Methylglycosid 10 der ED‐Disaccharideinheit dargestellt wird. Die Reaktion von 2 mit dem 6‐Iod‐monosaccharid 13 führt zum Disaccharid 11 in nur mäßiger Ausbeute. Seine anschließende Reduktion mit Tri‐n‐butylstannan verläuft komplex wie auch mit der Modellverbindung 13 gezeigt wird. Dagegen erhält man nach der N‐Iodsuccinimid‐Methode aus 2 und dem Saccarid 15 glatt das Disaccharid 17, dessen Partialhydrogenolyse zum Benzylglycosid 18 der ED‐Disaccharideinheit verschiedener Saccharid‐Cytostatica führt.
• US6353095B1
  申请人：——

  公开号：US6353095B1

  公开（公告）日：2002-03-05
• [EN] KETOALDONIC ACIDS HAVING FORMED STEREOGENIC CENTERS OF R CONFIGURATION: METHODS AND COMPOSITIONS
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：WO1993006227A1

  公开（公告）日：1993-04-01

  (EN) The present invention provides a ketoaldonic acid such as an octulosonic or nonulosonic acid having formed stereogenic center of R configuration, as well as methods of synthesizing the same.(FR) L'invention se rapporte à un acide cétoaldonique tel qu'un acide octulosonique ou nonulosonique ayant un centre stéréogénique formé présentant une configuration en R, ainsi qu'à des procédés de synthèse d'un tel acide.