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HRID2052226

反应详情

EQUATION

反应方程式

HRID 2052226 的结构方程式

REACTANTS

反应物

3
结构：CCO
HCID702

Ethanol

C2H6O

结构：ClC(Cl)Cl
HCID6212

Chloroform

CHCl3

结构：CO[C@H]1[C@H](O[C@H]2C[C@](C)(O)[C@H](C(=O)O)c3cc4c(c(O)c32)C(=O)c2c(O)cc3c(c2C4=O)O[C@@H]2O[C@@]3(C)[C@H](O)[C@@H](N(C)C)[C@@H]2O)O[C@@H](C)[C@H](OC)[C@@]1(C)OC
HCID152473

(2R,4R,5R,6R,11S,13S,14R)-11-[(6-Deoxy-3-C-methyl-2,3,4-tri-O-methyl-alpha-L-mannopyranosyl)oxy]-4-(dimethylamino)-3,5,8,10,13-pentahydroxy-6,13-dimethyl-9,16-dioxo-3,4,5,6,9,11,12,13,14,16-decahydro-2H-2,6-epoxytetraceno[1,2-b]oxocine-14-carboxylic acid (incorrect configuration definition!)

C38H47NO16

PRODUCTS

生成物

1
结构：CO[C@H]1[C@H](O[C@H]2C[C@](C)(O)Cc3cc4c(c(O)c32)C(=O)c2c(O)cc3c(c2C4=O)O[C@@H]2O[C@@]3(C)[C@H](O)[C@@H](N(C)C)[C@@H]2O)O[C@@H](C)[C@H](OC)[C@@]1(C)OC
HCID152474

4-(Dimethylamino)-3,5,8,10,13-pentahydroxy-6,13-dimethyl-9,16-dioxo-3,4,5,6,9,11,12,13,14,16-decahydro-2H-2,6-epoxytetraceno[1,2-b]oxocin-11-yl 6-deoxy-3-C-methyl-2,3,4-tri-O-methylhexopyranoside

C37H47NO14

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CO
溶剂HCID887

Methanol

CH4O

结构：CN(C)C=O
溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

A solution of 12.3 g of nogalamycinic acid in a mixture of 20 ml of DMF and 50 ml of CH3OH was prepared by heating. After the solution had stood at room temperature overnight, it was put on 500 g of silica and eluted with CHCl3 --MeOH starting with 99:1 and gradually increasing the concentration of CH3OH until a ratio of 4:1 was reached. The elution was followed by thin layer chromatography (tlc) (CHCl3 --MeOH--H2O; 78:20:2) and collecting those fractions containing only nogamycin (Rf 0.5). A total of 3.9 g was obtained. One and one-half grams was recrystallized from acetone-CH3OH (85:15). Obtained: 259 mg, mp 210°-215° C.; αD +273° (C 0.923, CHCl3); uv (EtOH) λmax nm 236 (ε51,700), 259 (ε25,850), 290 (ε10,050) and 478 (ε16,100); ir (Nujol) 3500, 1670, 1630, 1575, 1295, 1230, 1110, 1055, 1005, 920, 890, 838, 778, 762 and 724 cm-1 ; mass spectrum m/e 729; 'H NMR (d7 -DMF) 1.14, 1.23, 1.37, 1.69 (12 H, 4 CH3C), δ2.07-2.38, 2.83-3.0 (m, 4 H, 2 CH2), 2.42 [s, 6 H, (CH3)2N], δ3.13, 3.42, 3.52 (3 S, 9 H, 3 CH3O), 3.3-4.2 (m, CHO, CHN), 4.95 (m, 1 H, benzylic CHO), δ5.32 (d, 1 H, anomeric), δ5.68 (1 H, anomeric) δ7.16, 7.32 (2s, 2 H, aromatic); 13C NMR (CDCl3) δ15.2, 18.3, 24.2, 30.4 (4 CH3C), 30.8 (CH2), δ41.5 [(CH3)2N], δ44.1 (CH2) δ48.7, 59.0, 61.4 (3 CH3O), δ66.4-88.6 (CO and CN), δ96.79 and 99.81 (anomeric), δ113.1-161.4 (aromatic), δ179.7 and 190.8 (carbonyl). Anal. calcd. for C37H47NO14 : C, 60.96; H, 6.55; N, 1.92. Found: C, 58.55; H, 6.42; N, 1.94.

WORKUP

后处理

  1. customwas prepared
  2. temperatureby heating
  3. washeluted with CHCl3
  4. temperatureMeOH starting with 99:1 and gradually increasing the concentration of CH3OH until a ratio of 4:1
  5. washThe elution
  6. customcollecting those fractions
  7. additioncontaining only nogamycin (Rf 0.5)
  8. customA total of 3.9 g was obtained
  9. customOne and one-half grams was recrystallized from acetone-CH3OH (85:15)
  10. customObtained