beta-D-Ribofuranoside, methyl 2,3,5-tris-O-[(2,4-dichlorophenyl)methyl]- → 1-o-Methyl-3,5-bis-o-(2,4-dichlorobenzyl)-beta-d-ribofuranose

HRID 1270049

반응식

HRID 1270049 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>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

3

반응물 1

HCID 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

반응 조건

온도
3 °C

실험 절차

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

후처리

  1. customAfter a total reaction time of approximately 43 hours, the reaction was quenched
  2. additionby carefully adding the solution to 1.9 L of a saturated NaHCO3 solution
  3. customTin salts were removed via filtration through Celite after which the organic phase
  4. customwas isolated
  5. dry with materialdried with MgSO4
  6. customevaporated in vacuo
  7. customThe crude oil was used directly in the next step without further purification

출처 및 근거

ORD 기록
ord-0218ea5a44084fdabfd7e4f77d0ae961
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202223B2

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