methyl 2,3-O-isopropylidene-α-D-mannofuranoside | 27954-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-O-isopropylidene-α-D-mannofuranoside
• 英文别名: (1R)-1-[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]ethane-1,2-diol
• CAS: 27954-10-5
• 化学式: C₁₀H₁₈O₆
• 分子量: 234.249
• InChiKey: IKOWBTZQUCUCHP-DFTQBPQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3-O-isopropylidene-α-D-mannofuranoside 在 palladium dihydroxide Dowex 50W-X₈ 、 氢气 、 溴 、 二正丁基氧化锡 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， -78.0~25.0 ℃ 、344.73 kPa 条件下， 反应 104.67h， 生成 1-脱氧甘露伊霉素
  参考文献：
  名称：

  Expeditious Synthesis of Aza sugars by the Double Reductive Amination of Dicarbonyl Sugars

  摘要：

  Polyhydroxylated pyrrolidines and piperidines were prepared by the double reductive amination of dicarbonyl, sugars with primary amines and NaCNBH3 in MeOH. Stereocontrol in these reactions depended on the nature of the amine and dicarbonyl sugar. For example, 5-keto-D-fructose (7) gave three pyrrolidine stereoisomers, with the N-alkylated 2,5-anhydro-2,5-imino-D-glucitol predominating. Under similar reaction conditions with benzhydrylamine, 5-keto-D-glucose (20) afforded a 96:4 mixture of piperidines favoring D-gluco 25A, whereas 5-keto-D-mannose (6) produced a 67:33 mixture enriched in D-manno isomer 40. This method allowed for the direct and relatively short synthesis of 1-deoxynojirimycin (DNJ, 1) and 1-deoxymannojirimycin (DMJ, 5) and N-alkylated derivatives thereof. Similar reactions with O-protected 5-keto-D-glucose derivatives 21 and 22 were less stereoselective and lower yielding.

  DOI：

  10.1021/jo00090a040
• 作为产物：
  描述：

  4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 在 溶剂黄146 作用下， 反应 0.75h， 以95%的产率得到methyl 2,3-O-isopropylidene-α-D-mannofuranoside
  参考文献：
  名称：

  制备 5,6-Dideoxy-5-dimethylphosphinyl-D-和-L-hexofuranoses 的立体选择性，以及 5,6-Dideoxy-5-hydroxyphosphinyl-L-galactopyranose（P-in-the-Ring）的有效合成L-岩藻糖类似物）

  摘要：

  将膦酸二甲酯添加到 5 种 6-O-tosyl-hexofuranos-5-uloses 3a-e（α-D-xylo、α-D-ribo、β-D-arabino、α-D-lyxo 和 β -D-ribo) 在 DBU 存在下，然后在 Raney-Ni (W-4) 存在下催化氢解，得到 (5S)- 和 (5R)-5,6- 二脱氧-己呋喃糖衍生物1:0-2:1，取决于中间体5,6-二脱氧-己-5-烯呋喃糖的呋喃糖环的β-侧上的取代基种类。由 3-O-benzyl-5,6-dideoxy-1,2- 有效地制备了 L-岩藻糖类型的 P-in-the-ring 糖类似物 5,6-dideoxy-5-hydroxyphosphinyl-L-galactopyranoses O-异亚丙基-5-二甲氧基膦基-α-L-呋喃半乳糖很容易通过上述选择性制备得到。

  DOI：

  10.1246/bcsj.66.2315

文献信息

• Orientation of the Addition of Dimethyl Phosphonate to 5,6-Dideoxy-6-nitro-D-hex-5-enofuranoses
  作者：Tadashi Hanaya、Hiroshi Yamamoto、Hiroshi Yamamoto

  DOI：10.1246/bcsj.65.1154

  日期：1992.4

  The addition of dimethyl phosphonate to six 5,6-dideoxy-6-nitro-D-hex-5-enofuranoses at 25 °C in the presence of triethylamine preponderantly gave (5R)-adducts, whereas the same reaction at 100 °C without a base yielded (5S)-adducts as the main products.

  在三乙胺存在下，在 25 °C 下将膦酸二甲酯添加到六个 5,6-二脱氧-6-硝基-D-己基-5-烯呋喃糖中，主要产生 (5R)-加合物，而在 100 °C 下的反应相同a 碱以 (5S)-加合物为主要产物。
• Application of cyclic sulfates in the synthesis of 6-deoxy-d-manno-heptopyranose derivatives
  作者：Pieter A.M. van der Klein、Jacques H. van Boom

  DOI：10.1016/0008-6215(92)84105-2

  日期：1992.2

  6-Deoxy- d -manno-heptopyranose was prepared in five steps starting from methyl 2,3-O-isopropylidene-α- d -mannopyranoside 4,6-sulfate or methyl 2,3-O-isopropylidene-α- d -mannofuranoside 5,6-sulfate. The glycosyl donor ethyl 2,3,4,7-tetra-O-benzoyl-6-deoxyl-1-thio-α,β- d -manno-heptopyranoside was used to synthesise methyl 4-O-(6-deoxy-α- d -manno-heptopyranosyl)-β- d -galactopyranoside.

  摘要从2,3-O-异亚丙基-α-d-甘露吡喃糖苷4,6-硫酸甲酯或2,3-O-异亚丙基-α-d-甲基开始，分五步制备6-脱氧-d-甘露聚糖-七吡喃糖。 5，6-硫酸甘露呋喃糖苷。使用糖基供体乙基2,3,4,7-四-O-苯甲酰基-6-脱氧-1-硫代-α，β-d-甘露聚糖-七吡喃糖苷合成甲基4-O-（6-脱氧-α -d-甘露聚糖-七吡喃糖基）-β-d-吡喃半乳糖苷。
• Bicyclic diazasugars. Part 3: β-d-Mannose and 6-deoxy-β-l-gulose analogues
  作者：David A Berges、Jianmei Fan、Nannan Liu、N Kent Dalley

  DOI：10.1016/s0040-4020(01)01011-0

  日期：2001.12

  nitrogen atoms replacing the ring and glycosidic oxygen atoms has been prepared in a single step from 5-O-mesyl-d-mannofuranose by a process that likely involves double displacement and an epoxide intermediate. A similar but protected bicyclic analogue of 6-deoxy-β-l-gulopyranose has been prepared by an electrophilic cyclization reaction.

  β-d-甘露吡喃糖的双环类似物，其中氮原子取代了环和糖苷氧原子，是通过5 - O-甲磺酰基-d-甘露糖呋喃糖通过一步法制备的，该过程可能涉及两次置换和环氧化物中间体。已经通过亲电环化反应制备了类似但受保护的6-脱氧-β-1-戊吡喃糖的双环类似物。
• The endocyclic oxygen atom of d-mannopyranose is involved in its binding to pradimicins
  作者：Yasunori Watanabe、Fumiya Yamaji、Makoto Ojika、Takahiro Sugawara、Dai Akase、Misako Aida、Yasuhiro Igarashi、Yukishige Ito、Yu Nakagawa

  DOI：10.1016/j.tetlet.2019.151530

  日期：2020.2

  Methyl 5-thio-α-D-mannopyranoside (1) and six inositols were evaluated for their ability to bind to pradimicins (PRMs) via molecular modeling and three binding assays. In all the experiments, the binding affinity of 1 was slightly lower than that of methyl α-D-mannopyranoside (Man-OMe) and inositols hardly bound to PRMs. These results indicate that the endocyclic oxygen atom of Man-OMe is involved

  通过分子建模和三种结合试验评估了甲基5-硫代-α-D-甘露吡喃糖苷（1）和6种肌醇与大黄素（PRM）结合的能力。在所有的实验中，结合亲和力1略低于该甲基α-d-D-吡喃甘露糖苷（曼-OME）和肌醇的几乎不结合的PRM。这些结果表明Man-OMe的环内氧原子参与了其与PRM的结合。
• Stereoselective Synthesis of β-<i>C</i>-Allyl- and β-<i>C</i>-Propargyl-<scp>d</scp>-arabino­furanosides
  作者：C. Ramana、Sachin Narute、Rajesh Gonnade、Rahul Patil

  DOI：10.1055/s-2008-1067016

  日期：2008.6

  The stereoselective synthesis of β-configured C-allyl- and C-propargyl-d-arabinofuranosides (4,7-anhydro-1,2,3-deoxy-d-gluco-oct-1-enitols and -oct-1-ynitols) was addressed by employing allylation/propargylation of a dialdofuranose under aqueous Barbier reaction conditions and acid-catalyzed furan ring transposition of 5-O-mesyl-manno-oct-7-eno- or 5-O-mesyl-manno-oct-7-ynofuranoside derivatives.

  通过在水溶液中采用烯丙基化/丙炔基化反应，立体选择性地合成了δ-构型的 C-烯丙基和 C-丙炔基-d-阿拉伯呋喃糖（4,7-脱水-1,2、在巴比耶水溶液反应条件下，通过对二呋喃糖进行烯丙基化/丙炔基化反应，以及酸催化 5-O-甲砜基-甘露-辛-7-烯或 5-O-甲砜基-甘露-辛-7-炔呋喃糖苷衍生物的呋喃环转位，解决了 4,7-脱水-1,2,3-脱氧-d-葡萄糖-辛-1-烯糖醇和辛-1-炔糖醇的立体选择性合成问题。