| Identification | Back Directory | [Name]
[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate | [CAS]
253265-97-3 | [Synonyms]
[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate
[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-b]furanyl Succinimidyl Carbonate
(3R,3aS,6aR)-3-Hydroxyhexahydrofuro[2,3-b]furanyl Succinimidyl Carbonate
(3R,3AS,6AR)-3-HYDROXYHEXAHYDROFURO(2,3-B)FURANYL SUCCICINAMIDYL CARBONATE
2,5-Dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate
1-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}oxy)pyrrolidine-2,5-dione
1-[[[[(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]oxy]-2,5-pyrrolidinedione
1-[[[[(3R,3aS,6aR)-Hexahydrofuro[2,3-β]furan-3-yl]oxy]carbonyl]oxy]-2,5-pyrrolidinedione
Carbonic Acid 2,5-Dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-Hexahydrofuro[2,3-β]furan-3-yl] Ester
Carbonic Acid 2,5-Dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl] Ester | [EINECS(EC#)]
813-811-7 | [Molecular Formula]
C11H13NO7 | [MDL Number]
MFCD12031467 | [MOL File]
253265-97-3.mol | [Molecular Weight]
271.22 |
| Chemical Properties | Back Directory | [Appearance]
Pale-Yellow Solid | [Melting point ]
122-125℃ | [Boiling point ]
391.8±52.0 °C(Predicted) | [density ]
1.51 | [vapor pressure ]
0-0Pa at 20-25℃ | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly) | [form ]
Solid | [color ]
White | [InChI]
InChI=1S/C11H13NO7/c13-8-1-2-9(14)12(8)19-11(15)18-7-5-17-10-6(7)3-4-16-10/h6-7,10H,1-5H2/t6-,7-,10+/m0/s1 | [InChIKey]
VCFNCYVHQSHFRH-MHYGZLNHSA-N | [SMILES]
C(O[C@H]1CO[C@@]2([H])OCC[C@]21[H])(=O)ON1C(=O)CCC1=O | [LogP]
0.3 at pH7 |
| Hazard Information | Back Directory | [Chemical Properties]
Pale-Yellow Solid | [Uses]
Darunavir intermediate | [Synthesis]
1. 26.3 g of tert-butyl methyl ether, 35.09 g (135 mmol) of N,N'-disuccinimidyl carbonate, and 20.00 g (73.0% content) of (3R,3aS,6aR)-hexahydrofuro[2,3-B]furan-3-ol were mixed at room temperature, and the mixture was heated to 40 °C.
2. 11.89 g (150 mmol) of pyridine was added slowly and dropwise to the reaction mixture at 40 °C.
3. the reaction mixture was stirred at 40 °C for 22 hours.
4. Upon completion of the reaction, the reaction solution was cooled to 20 °C and 73.0 g of 2-propanol was slowly added dropwise at 20 °C to precipitate the target product 2,5-dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate.
5. The mixture was further cooled to 0-5°C and stirred at that temperature for 19 hours.
6. The precipitated target product was collected by filtration and washed with an appropriate solvent to give 27.83 g of product (97.8% content, 90% yield, enantiomeric excess >99.9% ee).
7. for the isolation of diastereoisomers, 30.0 g of tert-butyl methyl ether, 11.87 g of (3R,3aS,6aR)-hexahydrofuro[2,3-B]furan-3-ol containing 84.3% of the diastereoisomers, and the enzyme (CHIRAZYME L-2c, -flyo, Roche Diagnostics) were mixed at 25°C.
8. 3.31 g (38.4 mmol) of ethyl acetate was added dropwise to the mixture and the insoluble material was removed by filtration after stirring at 25 °C for 40 hours.
9. The filtrate was concentrated to give 12.73 g of a mixture containing (3R,3aS,6aR)-hexahydrofuro[2,3-B]furan-3-ol and its 3S,3aS,6aR isomer (90% yield, diastereoisomer ratio 100.0/0.0). | [References]
[1] Patent: JP2016/150901, 2016, A. Location in patent: Paragraph 0016; 0017; 0023; 0024
[2] Journal of Organic Chemistry, 2004, vol. 69, # 23, p. 7822 - 7829
[3] European Journal of Organic Chemistry, 2016, vol. 2016, # 10, p. 1874 - 1880
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 1813 - 1822
[5] Patent: WO2010/23322, 2010, A1. Location in patent: Page/Page column 29 |
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