Tin tetrachloride → 1-o-Methyl-3,5-bis-o-(2,4-dichlorobenzyl)-beta-d-ribofuranose

HRID 10159

반응식

HRID 10159 반응식
[CH3:1][O:2][C@@H:3]1[O:27][C@H:26]([CH2:28][O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=2[Cl:38])[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[C@H:4]1[O:5]CC1C=CC(Cl)=CC=1Cl.Cl[Sn](Cl)(Cl)Cl>C(Cl)Cl>[CH3:1][O:2][C@@H:3]1[O:27][C@H:26]([CH2:28][O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=2[Cl:38])[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[C@H:4]1[OH:5]

참가 물질

4

반응물 2

HCID 24287Tin tetrachlorideHCID 11767425beta-D-Ribofuranoside, methyl 2,3,5-tris-O-[(2,4-dichlorophenyl)methyl]-

생성물 1

HCID 674350681-o-Methyl-3,5-bis-o-(2,4-dichlorobenzyl)-beta-d-ribofuranose

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of the product of Step 1 (171.60 g, 0.2676 mol) in 1.8 L CH2Cl2 that was cooled to 0° C., was added dropwise a solution of stannous chloride (31.522 mL, 0.2676 mol) in 134 mL CH2Cl2 while stirring. After the solution was kept at 3° C. for 27 hours, another 5.031 ml of SnCl4 (0.04282 mol) was added and the solution was kept at 3° C. overnight. After 43 hours the reaction was quenched by carefully adding the solution to 1.9 L saturated NaHCO3 solution. Tin salts were removed via filtration through celite after which the organic phace was isolated, dried with MgSO4 and evaporated in vacuo. The yield of raw, dark yellow oil was 173.6 g, which contains 2,4-dibenzoyl chloride. The crude oil was used directly in the next step without further purification.

후처리

  1. waitthe solution was kept at 3° C. overnight
  2. customAfter 43 hours the reaction was quenched
  3. additionby carefully adding the solution to 1.9 L saturated NaHCO3 solution
  4. customTin salts were removed via filtration through celite after which the organic phace
  5. customwas isolated
  6. dry with materialdried with MgSO4
  7. customevaporated in vacuo
  8. customThe crude oil was used directly in the next step without further purification

출처 및 근거

ORD 기록
ord-72933cad450b4014b6b24b165b8c5239
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094768B2

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