2,6-Anhydro-D-glycero-D-gulo-heptonsaeure | 57129-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-Anhydro-D-glycero-D-gulo-heptonsaeure
• 英文别名: β-D-glucopyranonic acid；2,6-Anhydro-D-glycero-D-gulo-heptonic acid；(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-carboxylic acid
• CAS: 57129-89-2
• 化学式: C₇H₁₂O₇
• 分子量: 208.168
• InChiKey: MTNHERCZHBRCJQ-VFUOTHLCSA-N

物化性质

• 沸点：
  528.9±50.0 °C(Predicted)
• 密度：
  1.745±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,6-Anhydro-D-glycero-D-gulo-heptonsaeure 在 五氯化磷 、 zinc(II) chloride 作用下， 以 吡啶 为溶剂， 反应 24.0h， 生成 methyl 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-D-gulo-heptonate
  参考文献：
  名称：

  （Z）-3,7-脱水-1,2-二脱氧-2-氘-D-葡萄糖-辛-2-烯醇的合成，前手性底物用于探测葡糖基化酶的催化功能。

  摘要：

  标题化合物的合成提供了一种前手性的糖基供体底物，非常适合用作D-葡萄糖基动员酶催化功能的探针，因为酶反应在其双键的完全立体化学可以通过检查反应产物。合成的起始原料是2,6-脱水-D-甘油-D-古洛糖酸，从中得到3,7-脱水-4,5,6,8-四-O-苄基-1-脱氧-分八步制备D-甘油-D-gulo-2-辛糖。用氘化锂铝进行还原，并将所得非对映异构醇转化为（Z）-3,7-脱水-4,5,6,8-四-O-苄基-1,2-二脱氧-2-氘-D-葡萄糖-辛-2-烯醇（11）和3,7-脱水-4,5,6,8-四-O-苄基-1,2-二脱氧-2-氘-D-甘油-D-古洛辛进行了-1-烯醇（16）。副产品为3，7-脱水-2-O-苯甲酰基-4,5,6,8-四-O-苄基-1,2-二脱氧-2-氘-D-赤型-L-半乳糖辛醇和3,7-脱水-与化合物16一样，可以将2-O-苯甲酰基-4,5,6,8-四-O-苄基-1,2-二脱氧-

  DOI：

  10.1016/0008-6215(88)84081-3
• 作为产物：
  描述：

  (2R,3R,4S,5S,6R)-methyl tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-carboxylate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 生成 2,6-Anhydro-D-glycero-D-gulo-heptonsaeure
  参考文献：
  名称：

  由相应的脱水脱氧硝基醛糖醇（甘露糖基硝基甲烷）合成2，6-脱水醛糖酸并将其转化为甲酯，酰胺和醛糖醇

  摘要：

  摘要通过在碱性溶液中用过氧化氢氧化相应的脱水脱氧硝基醛糖醇（甘氨糖基硝基甲烷）得到了2,6-脱水醛糖酸。通过脱水醛酸甲基酯进行纯化。合成了5种2，6-脱水己酸和8种2，6-脱水庚酸，产率为44–81％。表征所有相应的未保护的和乙酰化的2，6-脱水醛酸甲基酯。前者的氨解以定量收率得到相应的酰胺。用硼氢化钠还原得到类似的脱水醛糖醇。

  DOI：

  10.1016/s0008-6215(98)00195-5

文献信息

• WEISER, WOLFGANG;LEHMANN, JOCHEN;BREWER, CURTIS F.;, HEHRE EDWARD J., CARBOHYDR. RES., 183,(1988) N 2, C. 287-299
  作者：WEISER, WOLFGANG、LEHMANN, JOCHEN、BREWER, CURTIS F.、, HEHRE EDWARD J.

  DOI：——

  日期：——
• PHARMACEUTICAL FORMULATIONS EMPLOYING SHORT-CHAIN SPHINGOLIPIDS AND THEIR USE
  申请人：HET NEDERLANDS KANKER INSTITUUT (The Netherlands Cancer Institute)

  公开号：EP1686959B1

  公开（公告）日：2009-06-24
• JPH05163300A
  申请人：——

  公开号：JPH05163300A

  公开（公告）日：1993-06-29
• Pharmaceutical formulations employing short-chain sphingolipids and their use
  申请人：Veldman J. Robert

  公开号：US20070082855A1

  公开（公告）日：2007-04-12

  This invention pertains to pharmaceutical formulations which comprise (i) a drug (e.g., an amphiphilic drug) (e.g., an anthracycline) (e.g., doxorubicin) and (ii) a short-chain sphingolipid (e.g., a short-chain glycosphingolipid or a short-chain sphingomyelin) (e.g., N-octanoyl-glucosylceramide, referred to as C 8 -GlcCer) (e.g., N-hexanoyl-sphingomyelin, referred to herein as C 6 -SM), and which provide improved drug delivery and efficacy. The short-chain sphingolipidis selected from compounds of the following formula: wherein: R 1 is independently: an O-linked saccharide group; or an O-linked polyhydric alcohol group; or: R 1 is independently: an O-linked (optionally N-(C 1-4 alkyl)-substituted amino)-C 1-6 alkyl-phosphate group; or an O-linked (polyhydric alcohol-substituted)-C 1-6 alkyl-phosphate group; R 2 is independently C 3-9 alkyl, and is independently unsubstituted or substituted; R 3 is independently C 7-19 alkyl, and is independently unsubstituted or substituted; R 4 is independently —H, —OH, or —O—C 1-4 alkyl; R N is independently —H or C 1-4 alkyl; the bond marked with an alpha (α) is independently a single bond or a double bond; if the bond marked with an alpha (α) is a double bond, then R 5 is —H; if the bond marked with an alpha (α) is a single bond, then R 5 is —H or —OH; the carbon atom marked (*) is independently in an R-configuration or an S-configuration; the carbon atom marked (**) is independently in an R-configuration or an S-configuration; and pharmaceutically acceptable salts, solvates, esters, ethers, chemically protected forms thereof. In one embodiment, the pharmaceutical formulation is a liposomal pharmaceutical formulation prepared using a mixture of lipids comprising, at least, vesicle-forming lipids (e.g., phospholipids) (e.g., phosphatidylcholines) (e.g., fully hydrogenated soy phosphatidylcholine (HSPC)) (e.g., dipalmitoyl-phosphatidylcholine (DPPC)) and said short-chain sphingolipid, and optionally cholesterol and optionally a vesicle-forming lipid which is derivatized with a polymer chain (e.g., a phosphatidylethanolamine (PE) which is derivatized with polyethyleneglycol (PEG)) (e.g., N-(carbonyl-methoxypolyethylene glycol 2000)-1,2-distearoyl-sn-glycero-3-phosphoethanolamine sodium salt (MPEG2000-DSPE). The present invention also pertains to methods for the preparation and use of such formulations.
• METHODS OF INCREASING THE BIOAVAILABILITY AND/OR CELLULAR UPDATE OF DRUGS
  申请人：VELDMAN Robert J.

  公开号：US20110150984A1

  公开（公告）日：2011-06-23

  This invention pertains to methods of increasing the bioavailability and/or cellular uptake of an amphiphilic drug when administered parenterally, which method comprises the step of parenterally co-administering the drug with a short-chain sphingolipid as described herein.