1,2-Dichloroethane → 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl cyanide

HRID 2291145노트

반응식

HRID 2291145 반응식
C(O[C@@H:5]1[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:6]1[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.ClCCCl.[C:42]([Si](C)(C)C)#[N:43].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:8]([O:7][C@@H:6]1[C@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:27][C@H:5]1[C:42]#[N:43])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoateHCID 82115Trimethylsilyl cyanideHCID 516892Sodium Bicarbonate

생성물 1

HCID 27289142,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl cyanide

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A stirred solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (50.3 g, 80 mmol), 1,2-dichloroethane (100 ml), and cyanotrimethylsilane (15.84 g, 160 mmol) was treated in one portion via a syringe with anhydrous stannic chloride (20.8 g, 9.33 ml, 80 mmol). The darkening solution was stirred for two minutes then poured into saturated sodium hydrogen carbonate (800 ml), and stirred five minutes (pH 7). Chloroform (1 liter) was added and the emulsion was filtered through Celite®. The chloroform layer was separated, dried (MgSO4) and evaporated under reduced pressure (15 torr, 40° ) to a light orange syrup which was crystallized from ethanol (charcoal to afford 2 (30 g from two crops, 80%) as long white needles; mp 77°-78° after drying at 0.05 torr, 60° for two hours; [α]D25 +24.4° (0.5 CHCl3).

후처리

  1. stirringstirred five minutes (pH 7)
  2. filtrationthe emulsion was filtered through Celite®
  3. customThe chloroform layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure (15 torr, 40° ) to a light orange syrup which
  6. customwas crystallized from ethanol (charcoal
  7. customto afford 2 (30 g from two crops, 80%) as long white needles
  8. custommp 77°-78° after drying at 0.05 torr, 60° for two hours

출처 및 근거

ORD 기록
ord-17a3785a33784a0cae2171fba7a1a85b
출처 데이터셋
uspto-grants-1986_10
특허 번호
US04619996

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