1,2,3,4,6-penta-O-acetyl-5a-carba-β-D-mannopyranose | 90694-06-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,4,6-penta-O-acetyl-5a-carba-β-D-mannopyranose
• 英文别名: (1R,2R,3S,4R,5R)-1,2,3,4-tetra-acetoxy-5-(acetoxymethyl)cyclohexane；Pseudo-β-D-mannopyranose pentaacetate；Pseudo-β-D-mannopyranose-pentaacetat；5a-carba-β-D-mannopyranose penta-acetate；[(1R,2R,3S,4R,5R)-2,3,4,5-tetraacetyloxycyclohexyl]methyl acetate
• CAS: 90694-06-7
• 化学式: C₁₇H₂₄O₁₀
• 分子量: 388.372
• InChiKey: NHQQATCRVHXHKV-HHARLNAUSA-N

物化性质

• 熔点：
  116-118 °C
• 沸点：
  420.2±38.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2,3,4,6-penta-O-acetyl-5a-carba-β-D-mannopyranose 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以86%的产率得到Pseudo-β-D-mannopyranose
  参考文献：
  名称：

  Paulsen, Hans; Deyn, Wolfgang von; Roeben, Wolfgang, Liebigs Annalen der Chemie, 1984, # 3, p. 433 - 449

  摘要：

  DOI：
• 作为产物：
  描述：

  1-phenyl-1,2-dideoxy-7-O-(phenoxythiocrbonyl)-4,5:6,8-di-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-D-talo-D-glycero-oct-1-yne 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 偶氮二异丁腈 、 四丁基氟化铵 、 氢气 、 三正丁基氢锡 、 sodium hydride 、 臭氧 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， -78.0~85.0 ℃ 、241.32 kPa 条件下， 反应 22.0h， 生成 1,2,3,4,6-penta-O-acetyl-5a-carba-β-D-mannopyranose
  参考文献：
  名称：

  Stereodivergent synthesis of 5a-carba-hexopyranoses from carbohydrates via 6-exo-dig radical cyclization: preparation of 5a-carba-β-d-manno-, α-d-allo-, β-l-talo- and α-l-gulopyranose pentaacetates from d-mannose

  摘要：

  Four carbasugars. 5a-carba-beta-D-manno-, alpha-D-allo-, beta-L-talo- and alpha-L-gulopyranose pentaacetates, have been prepared in a stereodivergent manner from D-mannose. Alkynyl derivatives of 2,3:4,6-di-O-isopropylidene-D-mannopyranose, which are prepared by homologation at C-1. by reaction with phenyl acetylide, undergo a 6-exo-dig radical cyclization, from a radical located at C-5. to yield a mixture of highly functionalized cyclohexanes. Some of these compounds, after transformation of their exocyclic double bond in a hydroxy function, were correlated with polyhydroxylated cyclohexanes, which were then selectively deoxygenated either at position C-4 or C-5a (carbohydrate numbering) to afford carbasugars of the D- Or L- series. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00532-9

文献信息

• A novel entry to 5a-carba-hexopyranoses from carbohydrates based on a 6-exo-dig radical cyclization: synthesis of 5a-carba-β-d-mannopyranose pentaacetate
  作者：Ana M. Gómez、Gerardo O. Danelón、Eduardo Moreno、Serafín Valverde、J. Cristóbal López

  DOI：10.1039/a808848i

  日期：——

  Carbohydrate-derived 2,3:4,6-diacetonides which are homologated at C-1 by reaction with phenyl acetylide undergo a 6-exo-dig radical cyclization, from a radical located at C-5, to yield highly functionalized cyclohexanes that are correlated with carba-sugars.

  来源于碳水化合物的2,3:4,6-二乙酰酮在C-1位置通过与苯乙炔反应进行 homologation，发生以C-5位置的自由基为中心的6-exo-dig自由基环化反应，生成与碳糖相关的高度功能化的环己烷。
• (−)-Quinic acid in organic synthesis. 2. Facile syntheses of pseudo-β-D-mannopyranose and pseudo-β-D-fructopyranose.
  作者：Tony K.M. Shing、Ying Tang

  DOI：10.1016/s0040-4020(01)86463-2

  日期：1991.1

  Pseudo-beta-D-mannopyranose (1) and pseudo-beta-D-fructopyranose (2) have been obtained from quinic acid in seven and twelve steps respectively.
• Cyclohexane polyols: Enantioselective synthesis of (+)-fortamine and of pseudosugars
  作者：Liu Pingli、Maurits Vandewalle

  DOI：10.1016/s0040-4020(01)85234-0

  日期：1994.1
• Takahashi, Tamiko; Kotsubo, Hironori; Iyobe, Akira, Journal of the Chemical Society. Perkin transactions I, 1990, # 11, p. 3065 - 3072
  作者：Takahashi, Tamiko、Kotsubo, Hironori、Iyobe, Akira、Namiki, Toshie、Koizumi, Toru

  DOI：——

  日期：——
• OGAWA, SEIICHIRO;UEMURA, MASAKI;FUJITA, TOICHI, CARBOHYDR. RES., 177,(1988) 213-221
  作者：OGAWA, SEIICHIRO、UEMURA, MASAKI、FUJITA, TOICHI

  DOI：——

  日期：——