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HRID461937

反应详情

EQUATION

反应方程式

HRID 461937 的结构方程式

REACTANTS

反应物

3
结构：O=S(=O)(O)O
HCID1118

Sulfuric acid

H2O4S

结构：[K+].[OH-]
HCID14797

Potassium hydroxide

HKO

结构：COC(=O)[C@@H]1c2cc3c(c(O)c2[C@@H](O[C@@H]2O[C@@H](C)[C@H](OC)[C@@](C)(OC)[C@H]2OC)C[C@]1(C)O)C(=O)c1c(O)cc2c(c1C3=O)O[C@@H]1O[C@@]2(C)[C@H](O)[C@@H](N(C)C)[C@@H]1O
HCID5289019

Nogalamycin

C39H49NO16

PRODUCTS

生成物

1
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

AUXILIARIES

试剂、催化剂与溶剂

4
结构：CCO
溶剂HCID702

Ethanol

C2H6O

结构：CO
溶剂HCID887

Methanol

CH4O

2 次

结构：O
溶剂HCID962

Water

H2O

2 次

结构：ClC(Cl)Cl
溶剂HCID6212

Chloroform

CHCl3

PROCEDURE

实验过程

Forty grams (0.05 mole) of nogalamycin was dissolved in 356 ml of 1 N KOH (0.36 mole), and 310 ml of water was added. The solution was stirred overnight at room temperature. The reaction mixture was acidified to pH 3.0 by adding 30% H2SO4 dropwise with stirring. The precipitate was collected by centrifugation and the precipitate was washed three times with water. The dried product weighted 28.5 g. Ten grams was dissolved in 125 ml of methanol and put on 500 g of silica packed in CHCl3 --MeOH (95:5). Developed with CHCl3 --MeOH (95:5) increasing gradually to CHCl3 --MeOH (4:1). Elution was continued with CHCl3 --MeOH (1:1) until nogalamycinic acid had been eluted as determined by thin layer chromatography (tlc) using CHCl3 --MeOH--H2O (78:20:2). Evaporation in vacuo of the fractions containing chromatographically pure material gave a red solid, wt. 2.3 g; mp 219°-229° C.; Rf (tlc, CHCl3 --MeOH--H2O; 78:20:2) 0.25; αD +456° (C 0.37, CH3OH); uv (EtOH) λmax nm 236 (ε 39,950), 269 (ε 21,350), 291 sh (ε 8,700), 482 (13,550); ir (Nujol) 3450, 1670, 1630, 1595, 1580, 1290, 1230, 1215, 1135, 1095, 1060, 1015, 980, 920, 855, 830, 780, 763 and 725 cm-1 ; mass spectrum m/e 729 (M- --CO2); 'H NMR (CDCl3 --CD3OD) δ 1.38 (m, 9 H, 3 CH3C), δ 1.80 (s, 3 H, CH3C), δ 3.15 (s, 6H, (CH3)2NH+), δ 3.38, 3.40, 3.68 (3 s, 9 H, 3 CH3O), δ 3.2-4.0 (m, CHO and CHN), δ 5.24 (d, 1 H, anomeric), δ 5.88 (d, 1 H, anomeric), δ 6.92 (s, 1 H, aromatic) and δ 7.47 (s, 1 H, aromatic); 13C NMR (CDCl3 --CD2OD) 16.4, 19.3, 24.6, 31.5 (4 CH3C), δ 42.5 [(CH3)2N], δ 49.9, 58.2, 60.3, 62.5, 67.8, 68.5, 70.6, 71.6, 74.0, 77.3, 79.6, 82.1 and 85.9 (CH3O, CHO and CHN), δ 97.3 and 100.2 (anomeric), δ 113.1, 114.1, 116.0, 120.7, 125.8, 131.0, 132.5, 137.2, 147.4, 147.8, 156.0 and 161.4 (aromatic), δ 178.9, 181.9, 181.6 and 191.4 (carbonyl).

WORKUP

后处理

  1. stirringwith stirring
  2. customThe precipitate was collected by centrifugation
  3. washthe precipitate was washed three times with water
  4. dissolutionTen grams was dissolved in 125 ml of methanol
  5. temperatureDeveloped with CHCl3 --MeOH (95:5) increasing gradually to CHCl3 --MeOH (4:1)
  6. washElution
  7. washhad been eluted
  8. customEvaporation in vacuo of the fractions
  9. additioncontaining chromatographically pure material
  10. customgave a red solid, wt. 2.3 g