Methanol → HCID 13080730, 화합물

HRID 1159588노트

반응식

HRID 1159588 반응식
[Si:1]([O:8][CH2:9][C@@H:10]1[C@@H:17]2[C@@H:13]([O:14][C:15](=[O:18])[CH2:16]2)[CH2:12][C@H:11]1[O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.CO.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C(OCC)C>[Si:1]([O:8][CH2:9][C@@H:10]1[C@@H:17]2[C@@H:13]([O:14][CH:15]([OH:18])[CH2:16]2)[CH2:12][C@H:11]1[O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 887MethanolHCID 9855836Potassium sodium tartarateHCID 13080724(3aR,4S,5R,6aS)-4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-5-[(oxan-2-yl)oxy]hexahydro-2H-cyclopenta[b]furan-2-oneHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 13080730HCID 13080730, 화합물

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3283Diethyl Ether용매

반응 조건

온도
-78 °C

실험 절차

A solution of (3aR,4S,5R,6aS) -4-(t-butyldimethylsilyloxymethyl)-5-(2-tetrahydropyranyloxy)hexahydrocyclopenta[b]furan-2-one (22) (96.7 g, 261 mmol) in toluene (600 ml) was cooled to −75° C. 1.5M-diisobutyl aluminum hydride (261 ml, 392 mmol) was added thereto drop wise and the mixture was stirred at −78° C. for approximately 2 hours. After adding methanol (69.0 ml, 1703 mmol) drop wise to the solution, the solution was warmed to room temperature. Saturated aqueous potassium sodium tartrate (800 ml) and diethyl ether (400 ml) were added thereto and the mixture was stirred for one hour, let to stand and then separated into two layers. The aqueous layer was extracted twice with diethyl ether (400 ml). The organic layers were combined, washed twice with saturated aqueous sodium chloride (800 ml) and then dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure to give (3aR,4S,5R,6aS)-4-(t-butyldimethylsilyloxymethyl)-5-(2-tetrahydropyranyloxy)hexahydrocyclopenta[b]furan-2-ol (23) (97.8 g, quantitatively) as a slightly yellow oil.

후처리

  1. temperaturethe solution was warmed to room temperature
  2. stirringthe mixture was stirred for one hour
  3. customseparated into two layers
  4. extractionThe aqueous layer was extracted twice with diethyl ether (400 ml)
  5. washwashed twice with saturated aqueous sodium chloride (800 ml)
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationThe solution was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4f22911b036240c3810ec086bf34231b
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812182B2

반응 노트

불러오는 중…