(3aS,4R,6S,7S,7aR)-6-[(R)-Acetoxy-((1S,2S,3S,4R,5S,6S)-3-acetoxy-5-chloro-6-phenylselanyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-methyl]-7-benzyloxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester | 174782-46-8

• 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: (3aS,4R,6S,7S,7aR)-6-[(R)-Acetoxy-((1S,2S,3S,4R,5S,6S)-3-acetoxy-5-chloro-6-phenylselanyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-methyl]-7-benzyloxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester
• CAS: 174782-46-8
• 化学式: C₄₁H₄₆ClNO₁₀Se
• 分子量: 827.23
• InChiKey: WWKLJCXQXKWCGF-KXALBDAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  54.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  119.06
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6S,7S,7aR)-6-[(R)-Acetoxy-((1S,2S,3S,4R,5S,6S)-3-acetoxy-5-chloro-6-phenylselanyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-methyl]-7-benzyloxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(3aS,4R,6S,7S,7aR)-6-[(R)-Acetoxy-((1S,2S,3S,4R)-3-acetoxy-5-chloro-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-methyl]-7-benzyloxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester
  参考文献：
  名称：

  D-altrose衍生物的β-D-（1→3）-C键合的1,5,6-三苯氧基-1,5-亚氨基半乳糖苷的合成

  摘要：

  标题氮杂-C-二糖是通过2,6,7-三苯氧基-2,6-亚氨基-D-甘油-L-甘露糖和7-氧杂草烷酮衍生物的高度立体选择性交叉醛缩醛化获得的。

  DOI：

  10.1016/0040-4039(95)02214-7
• 作为产物：
  描述：

  (3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2,4-trimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 碳酸氢钠 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 33.5h， 生成 (3aS,4R,6S,7S,7aR)-6-[(R)-Acetoxy-((1S,2S,3S,4R,5S,6S)-3-acetoxy-5-chloro-6-phenylselanyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-methyl]-7-benzyloxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester
  参考文献：
  名称：

  D-altrose衍生物的β-D-（1→3）-C键合的1,5,6-三苯氧基-1,5-亚氨基半乳糖苷的合成

  摘要：

  标题氮杂-C-二糖是通过2,6,7-三苯氧基-2,6-亚氨基-D-甘油-L-甘露糖和7-氧杂草烷酮衍生物的高度立体选择性交叉醛缩醛化获得的。

  DOI：

  10.1016/0040-4039(95)02214-7

文献信息

• Aza-<i>C</i>-disaccharides:  Synthesis of 6-Deoxygalactonojirimycin β-C(1→3) Linked with <scp>d</scp>-Altrofuranosides and <scp>d</scp>-Galactose
  作者：Alain Baudat、Pierre Vogel

  DOI：10.1021/jo970151t

  日期：1997.9.1

  Cross-aldolization of 3-O-benzyl-N-(benzyloxycarbonyl)-2,6,7-trideoxy-2,6-imino-4,5-O-isopropylidene-beta-D-glycero-L-mannoheptose ((-)- 12, derived from D-glycero-D-gulo-heptono-1,4-lactone in eight steps with (+)-(1R,4S,5S,6S)- and (-)-(1S,4R,5R,6R)-6-chloro-5-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-one (obtained in one step from the ''naked sugars'' (-)- and (+)-7-oxabicyclo[2,2.1]hept-5-en-2-one) were highly stereoselective (lithium enolates, like modes, giving aldols (-)- 14 and (+)- 16, respectively. Stereoselective methods were developed for the conversion of(-)- 14 into methyl -imino-beta-D-glycero-L-manno-heptitol-1'-yl]-alpha and -beta-D-altro-furanoside ((+)-1 alpha,beta). The aza-C-disaccharide 1 alpha prefers a anti conformation (bonds C(2')-C(3') and C(1')-C(3) are antiperiplanar) for the beta-D-galactoside moiety ((3)J(H,H) coupling constants, NOEs). Aldol(+)- 16 was converted stereoselectively into 3-deoxy-3-C-[(1'S)-2',6',7'-trideoxy -2 D-glycero-L-manno-heptitol-1'-yl]-beta-D-galactose trifluoroacetate.