173192-39-7Relevant articles and documents
Ru-catalyzed asymmetric transfer hydrogenation of α-acyl butyrolactone via dynamic kinetic resolution: Asymmetric synthesis of bis-THF alcohol intermediate of darunavir
More, Ganesh V.,Malekar, Pushpa V.,Kalshetti, Rupali G.,Shinde, Mahesh H.,Ramana, Chepuri V.
, (2021)
The Ru-catalyzed enantio- and diastereoselective dynamic kinetic resolution of α-(benzyloxy/benzoyloxy)acyl-γ-butyrolactones has been examined via transfer hydrogenation. Employing the in situ prepared (R,R)-Ru-FsDPEN catalyst, the transfer hydrogenation of using formic acid/triethylamine at rt gave the corresponding (S)-3-((S)-2-(benzyloxy/benzoyloxy)-1-hydroxyethyl)dihydrofuran-2(3H)-one with good to excellent diastereo- and enantioselectivity. One of the resulting hydrogenation product prepared on gram scales was utilized for the synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3–b]furan-3-ol (1), a key synthetic intermediate of various HIV protease inhibitors such as darunavir with excellent enantio- (95% ee) and diastereoselectivities (dr 95:5).
Synthesis of hexahydro furo [2, 3 - b] furan - 3 - ol and its enantiomer
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Paragraph 0027-0029, (2017/08/03)
The invention discloses synthetic methods of hexahydrofuro[2,3-b]furan-3-ol and an enantiomer thereof. The synthetic method of hexahydrofuro[2,3-b]furan-3-ol comprises the step c or the step b to the step c or the step a to the step c in the following synthetic route as shown in the description. The synthetic method of the enantiomer (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-ol comprises the step c to the step f or the step b to the step f or the step a to the step f in the following synthetic route as shown in the description, wherein R1 is selected from C1 to C4 alkyl or aralkyl, and R2 is selected from C1 to C4 alkyl. The synthetic methods provided by the invention have the advantages of cheap and easily available raw materials, simple operation, low cost and the like, are suitable for large-scale production, and have practical value for realization of industrialized production of darunavir.
Enzymatic process for the preparation of butyrolactones
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, (2013/09/12)
The invention relates to a process for the preparation of a compound of formula wherein R1 is selected from the group consisting of hydrogen, C2-11-acyl, C4-9-cycloalkanoyl, aryl, aralkyl, aroyl, hetaryl, hetaralkyl and hetaroyl, comprising a biotransformation of a compound of formula wherein R1 is as defined above, wherein said biotransformation is carried out using a polypeptide having aldo-keto reductase activity or a microorganism containing same.
Production method of hexahydrofurofuranol derivative, intermediate therefor and production method thereof
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, (2008/06/13)
The present invention provides a method for producing compound (XIV) useful as an intermediate for pharmaceutical agents efficiently and economically on an industrial scale without using ozone oxidation and highly toxic reagent, and an intermediate used for this method. Particularly, the present invention provides a method for producing a compound having an absolute configuration represented by the formula (XV) and an enantiomer thereof without using a technique such as optical resolution and the like, and an intermediate used for this method. (1) Compound (XIII) as a starting material is led to compound (I), and after introducing a protecting group, subjected to reduction and cyclization to give compound (XIV). Particularly, compound (XIII) as a material is led to compound (I) via compound (XX) to produce compound (XIV). Using an optically active compound (XIII) as a starting material, a compound having an absolute configuration represented by the formula (XV) and the like are produced highly stereoselectively. (2) Compound (XXI) as a starting material is stereoselectively reduced to give compound (XXII), and by introduction of a protecting group, reduction and cyclization, compound (XXVI) is obtained, and by inverting hydroxyl group, compound (XV) is produced. wherein each symbol is as defined in the specification.
Pyrrolopyrazolopyrimidine compound and medicine comprising the same as active ingredient
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, (2008/06/13)
The invention relates to compounds represented by the following general formula (1): STR1 wherein R1 represents an alkyl group, R2 represents an amino group, alkyl group or the like, and R3 represents a nitro group, amino group, heterocyclic group, alkylsulfonylamino group or the like, or salts thereof, medicines comprising such a compound, a preparation process of the compounds, and intermediates useful for preparation thereof. The compounds (1) are useful for the prevention and treatment of a respiratory disease.
