3,5-di-O-benzyl-D-xylono-γ-lactone | 131139-04-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-di-O-benzyl-D-xylono-γ-lactone
• 英文别名: 3,5-di-O-benzyl-D-xylopenta-1,4-lactone；(3R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxydihydrofuran-2(3H)-one；3,5-di-O-benzyl-D-xylono-1,4-lactone；3,5-dibenzyl xylolactone；(3R,4R,5R)-3-hydroxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-one
• CAS: 131139-04-3
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: QPXJSNKRFKGBHM-KURKYZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-di-O-benzyl-D-xylono-γ-lactone 在 palladium on activated charcoal 吡啶 、 4 A molecular sieve 、 氢气 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.67h， 生成 (2S,3S,4R)-3-Hydroxy-4-trifluoromethanesulfonyloxymethyl-oxetane-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Oxetane δ‐Amino Acids: Chemoenzymatic Synthesis of 2,4‐Anhydro‐5‐N‐(t‐butoxycarbonyl)amino‐D‐lyxonic Acid

  摘要：

  Starting from 1,2-O-isopropylidene-D-xylose, methyl 2,4-anhydro-3,5-di-O-benzyl-D-lyxonate ( 4) was synthesized. Debenzylation and transformation of the primary hydroxyl group yielded methyl 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonate (9). While transesterification of 4 under basic reaction conditions was straightforward, an analogous reaction with 9 was not successful. After screening of several lipases, the enzymatic transesterification of 9 was achieved with lipase L2 from Candida antarctica to furnish the title compound 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonic acid in excellent yield. The stereochemistry at the oxetane ring was proven by an x-ray structure of the intermediate methyl 2,4-anhydro-5-azido-D-lyxonate.[GRAPHICS]

  DOI：

  10.1080/07328300600732485
• 作为产物：
  描述：

  3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 在 溴 、 barium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 3,5-di-O-benzyl-D-xylono-γ-lactone
  参考文献：
  名称：

  Ring contraction of 2-o-trifluoromethanesulphonates of α-hydroxy-γ-lactones to oxetane carboxylic esters

  摘要：

  DOI：

  10.1016/s0040-4039(00)97734-7

文献信息

• Metal-Free Iodine-Mediated Deoxygenation of Alcohols in the Position α to Electron-Withdrawing Groups
  作者：Maëva M. Pichon、Fabien Stauffert、Luis G. Addante-Moya、Anne Bodlenner、Philippe Compain

  DOI：10.1002/ejoc.201800051

  日期：2018.4.9

  The use of a substoichiometric amount of molecular iodine in the presence of PPh3 and pyridine effects a direct deoxygenation of primary and secondary alcohols in positions α to a variety of activating electron‐withdrawing groups, including ketones, esters, amides, imides and nitrile groups.

  在 PPh3 和吡啶的存在下，使用亚化学计量的分子碘可将 α 位的伯醇和仲醇直接脱氧为各种活化的吸电子基团，包括酮、酯、酰胺、酰亚胺和腈基。
• [EN] PROCESSES FOR PREPARING 2-DIHALO RIBOLACTONES<br/>[FR] PROCÉDÉS DE PRÉPARATION DE 2-DIHALO-RIBOLACTONES
  申请人：COCRYSTAL PHARMA INC

  公开号：WO2017075590A3

  公开（公告）日：2017-07-20
• Synthesis and epimerisation studies on carbohydrate derived bicyclic tetronate esters: The synthesis of furanofurans related to the cytotoxic metabolite goniofufurone
  作者：Cristiano Cagnolini、Marina Ferri、Peter R. Jones、Patrick J. Murphy、Barry Ayres、Brian Cox

  DOI：10.1016/s0040-4020(97)00164-6

  日期：1997.3

  The synthesis of the D-xylo- 12, D-lyxo- 13, D-ribo- 14 and D-arabino-furanofurans 15 was accomplished from the readily available butyrolactones 4 and 5 via a non-classical Wittig cyclisation/hydrogenation sequence; these compounds are analogues of the cytotoxic natural product goniofufurone. (C) 1997 Elsevier Science Ltd.
• WITTY, D. R.;FLECT, G. W. J.;VOGT, K.;WILSON, F. X.;WANG, Y.;STORER, R.;M+, TETRAHEDRON LETT., 31,(1990) N3, C. 4787-4790
  作者：WITTY, D. R.、FLECT, G. W. J.、VOGT, K.、WILSON, F. X.、WANG, Y.、STORER, R.、M+

  DOI：——

  日期：——