(3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-[(S)-((1R,2S,4S,5R,6R)-5-chloro-3-oxo-6-phenylselanyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-hydroxy-methyl]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester | 193409-79-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-[(S)-((1R,2S,4S,5R,6R)-5-chloro-3-oxo-6-phenylselanyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-hydroxy-methyl]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester
• 英文别名: benzyl (3aS,4R,6S,7S,7aR)-6-[(S)-[(1R,2S,4S,5R,6R)-5-chloro-3-oxo-6-phenylselanyl-7-oxabicyclo[2.2.1]heptan-2-yl]-hydroxymethyl]-2,2,4-trimethyl-7-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridine-5-carboxylate
• CAS: 193409-79-9
• 化学式: C₃₇H₄₀ClNO₈Se
• 分子量: 741.139
• InChiKey: LMDNTZCSACZFKO-IEPVGKILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  48
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-[(S)-((1R,2S,4S,5R,6R)-5-chloro-3-oxo-6-phenylselanyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-hydroxy-methyl]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 (3aS,4R,6R,7S,7aR)-7-Benzyloxy-6-((1S,2R,6S,7R,8R,9R,10R)-4,4-di-tert-butyl-10-chloro-9-phenylselanyl-3,5,11-trioxa-4-sila-tricyclo[6.2.1.0^2,7]undec-6-yl)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester
  参考文献：
  名称：

  Aza-C-disaccharides:  Synthesis of 6-Deoxygalactonojirimycin β-C(1→3) Linked with d-Altrofuranosides and d-Galactose

  摘要：

  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.

  DOI：

  10.1021/jo970151t
• 作为产物：
  描述：

  (3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-((S)-1,2-dihydroxy-ethyl)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester 在 sodium periodate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.58h， 生成 (3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-[(S)-((1R,2S,4S,5R,6R)-5-chloro-3-oxo-6-phenylselanyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-hydroxy-methyl]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester
  参考文献：
  名称：

  Aza-C-disaccharides:  Synthesis of 6-Deoxygalactonojirimycin β-C(1→3) Linked with d-Altrofuranosides and d-Galactose

  摘要：

  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.

  DOI：

  10.1021/jo970151t