allyl 2-<(3S)-3-(benzyloxy)tetradecanamido>-2-deoxy-4,6-O-isopropyliden-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranoside | 138527-86-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: allyl 2-<(3S)-3-(benzyloxy)tetradecanamido>-2-deoxy-4,6-O-isopropyliden-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranoside
• 英文别名: [(4aR,6S,7R,8R,8aS)-2,2-dimethyl-7-[[(3S)-3-phenylmethoxytetradecanoyl]amino]-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] (3R)-3-tetradecanoyloxytetradecanoate
• CAS: 138527-86-3
• 化学式: C₆₁H₁₀₅NO₁₀
• 分子量: 1012.51
• InChiKey: HSGDVRURDMKEKG-KKBKTFHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.8
• 重原子数：
  72
• 可旋转键数：
  47
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  allyl 2-<(3S)-3-(benzyloxy)tetradecanamido>-2-deoxy-4,6-O-isopropyliden-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranoside 在 N-[(2,4-二氯苯氧基)-甲氧基硫代膦酰]丙-2-胺 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 4.83h， 生成 allyl 2-<(3S)-3-(benzyloxy)tetradecanamido>-6-O-(tert-butyldimethylsilyl)-2-deoxy-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranoside
  参考文献：
  名称：

  2,6-二脱氧-6-氟-2-[（3R和3S）-3-羟基十四烷酰胺基] -3-O-[（3R）-3-（十四烷酰氧基）四癸酰基] -D-吡喃葡萄糖4-（磷酸二氢）和2-脱氧-2-[（（3R和3S）-3-羟基十四烷酰胺基] -3-O-[（3R）-3-（十四烷氧基）四癸酰基]-α-D-吡喃葡萄糖基氟化物4-（二氢磷酸盐）：GLA-60的氟糖类似物。

  摘要：

  Both 2,6-dideoxy-6-fluoro-2-[(3R)- and (3S)-3-hydroxytetradecanamido]-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glucopyranose 4-phosphate, 11 and 11' (6-fluoro GLA-60 and its 3'-epimer), and 2-deoxy-2[(3R)- and (3S)-(3-hydroxytetradecanamido]-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-alpha-D-glucopyranosyl fluoride 4-(dihydrogen phosphate), 18 and 18' (1-fluoro GLA-60 and its 3'-epimer), were synthesized from ally 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-alpha-D-glucopyranoside.

  DOI：

  10.1016/0008-6215(91)89008-4
• 作为产物：
  描述：

  (+/-)-3-(benzyloxy)tetradecanoic acid 在 N-[(2,4-二氯苯氧基)-甲氧基硫代膦酰]丙-2-胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 allyl 2-<(3S)-3-(benzyloxy)tetradecanamido>-2-deoxy-4,6-O-isopropyliden-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranoside
  参考文献：
  名称：

  2,6-二脱氧-6-氟-2-[（3R和3S）-3-羟基十四烷酰胺基] -3-O-[（3R）-3-（十四烷酰氧基）四癸酰基] -D-吡喃葡萄糖4-（磷酸二氢）和2-脱氧-2-[（（3R和3S）-3-羟基十四烷酰胺基] -3-O-[（3R）-3-（十四烷氧基）四癸酰基]-α-D-吡喃葡萄糖基氟化物4-（二氢磷酸盐）：GLA-60的氟糖类似物。

  摘要：

  Both 2,6-dideoxy-6-fluoro-2-[(3R)- and (3S)-3-hydroxytetradecanamido]-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glucopyranose 4-phosphate, 11 and 11' (6-fluoro GLA-60 and its 3'-epimer), and 2-deoxy-2[(3R)- and (3S)-(3-hydroxytetradecanamido]-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-alpha-D-glucopyranosyl fluoride 4-(dihydrogen phosphate), 18 and 18' (1-fluoro GLA-60 and its 3'-epimer), were synthesized from ally 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-alpha-D-glucopyranoside.

  DOI：

  10.1016/0008-6215(91)89008-4

文献信息

• Lipid A analogues having immunoactivating and anti-tumour activity
  申请人：Sankyo Company Limited

  公开号：EP0437016A2

  公开（公告）日：1991-07-17

  Compounds of formula (I): [in which: R1 is hydroxy, protected hydroxy, fluorine, or -OP(0)(OH)2; R2 and R3 are independently optionally substituted C6 - C20 aliphatic acyl; R4 is hydroxy, protected hydroxy, or -OP(O)(OH)2, where at least one of R1 and R4 is -OP(O)(OH)2; and R5 is hydroxy, protected hydroxy, or fluorine; provided that, except where at least one of R1 and R5 is fluorine, then at least one of R2 and R3 is a substituted C6 - C20 aliphatic acyl having (i) at least one halogen substituent and (ii) at least one of halogen, hydroxy and C6 - C20 aliphatic acyloxy or at least one of R2 and R3 is a substituted C6 - C20 aliphatic acyl which is substituted by at least one halogen-substituted C6 - C20 aliphatic carboxylic acyloxy]; have Lipid A-like activity and may be used for the treatment, prophylaxis, diagnosis and support of an animal suffering a disease or disorder arising from a deficiency in the immune system or from a tumor. They may be prepared by phosphorylation of corresponding compounds lacking a phosphoryl group.

  式(I)化合物： 其中R1 是羟基、受保护的羟基、氟或-OP(0)(OH)2；R2 和 R3 独立地是任选取代的 C6 - C20 脂肪族酰基；R4 是羟基、受保护的羟基或-OP(O)(OH)2，其中 R1 和 R4 中至少有一个是-OP(O)(OH)2；R5 是羟基、受保护的羟基或氟；条件是，除非 R1 和 R5 中至少有一个是氟，否则 R2 和 R3 中至少有一个是被取代的 C6 - C20 脂肪族酰基，该酰基具有 (i) 至少一个卤素取代基和 (ii) 卤素、羟基和 C6 - C20 脂肪族酰氧基中的至少一个，或者 R2 和 R3 中至少有一个是被至少一个卤素取代的 C6 - C20 脂肪族羧基酰氧基取代的 C6 - C20 脂肪族酰基]；具有类似脂质 A 的活性，可用于治疗、预防、诊断和支持因免疫系统缺陷或肿瘤引起的疾病或紊乱的动物。它们可以通过对缺乏磷酸基团的相应化合物进行磷酸化来制备。
• Syntheses of 2,6-dideoxy-6-fluoro-2-[(3R and 3S)-3- hydroxytetradecanamido]-3-O-[(3R)-3-(tetradecanoyloxy)- tetradecanoyl]-d-glucopyranose 4-(dihydrogen phosphate) and 2-deoxy-2-[(3R and 3S)-3-hydroxytetradecanamido]- 3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-α-d-glucopyranosyl fluoride 4-(dihydrogen phosphate): fluorosugar analogues of GLA-60
  作者：Yoshiyuki Kobayashi、Nobory Ishida、Masami Arai、Masao Shiozaki、Tetsuo Hiraoka、Masahiro Nishijima、Sayuri Kuge、Toshiaki Otsuka、Yuzuru Akamatsu

  DOI：10.1016/0008-6215(91)89008-4

  日期：1991.12

  Both 2,6-dideoxy-6-fluoro-2-[(3R)- and (3S)-3-hydroxytetradecanamido]-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glucopyranose 4-phosphate, 11 and 11' (6-fluoro GLA-60 and its 3'-epimer), and 2-deoxy-2[(3R)- and (3S)-(3-hydroxytetradecanamido]-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-alpha-D-glucopyranosyl fluoride 4-(dihydrogen phosphate), 18 and 18' (1-fluoro GLA-60 and its 3'-epimer), were synthesized from ally 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-alpha-D-glucopyranoside.