166337-67-3

Upstream product

• 501-53-1 benzyl chloroformate 
• 1709-44-0 m-aminobenzaldehyde 
• 1228657-98-4 C₁₉H₂₂N₂O₃ 
• 135429-73-1 3-(benzyloxycarbonyl)aminobenzyl alcohol 
• 1877-77-6 3-aminobenzenemethanol 

Downstream Products

• 166337-66-2 [3-(1-Hydroxy-2-methyl-propyl)-phenyl]-carbamic acid benzyl ester 
• 166337-92-4 [3-(1-Hydroxypentyl)phenyl]-carbamic acid, phenylmethyl ester 
• 166337-68-4 [3-(1-Hydroxybutyl)phenyl]-carbamic acid, phenylmethyl ester 
• 166336-69-2 {3-[1-(4-Hydroxy-2-oxo-5,6,7,8,9,10-hexahydro-2H-cycloocta[b]pyran-3-yl)-pentyl]-phenyl}-carbamic acid benzyl ester 
• 166336-73-8 {3-[1-(4-Hydroxy-2-oxo-5,6,7,8,9,10-hexahydro-2H-cycloocta[b]pyran-3-yl)-3-methyl-butyl]-phenyl}-carbamic acid benzyl ester 
• 166336-29-4 [3-[1-(5,6,7,8,9,10-Hexahydro-4-hydroxy-2-oxo-2H-cycloocta[b]pyran-3-yl)butyl]phenyl]-carbamic acid, phenylmethyl ester 
• 166336-24-9 [3-[1-(5,6,7,8,9,10-Hexahydro-4-hydroxy-2-oxo-2H-cycloocta[b]pyran-3-yl)-2-methylpropyl]phenyl]-carbamic acid, phenylmethyl ester 

Relevant academic research and scientific papers

Preparation of acetals from aldehydes and alcohols under basic conditions

A new, simple protocol for the synthesis of acetals under basic conditions from non-enolizable aldehydes and alcohols has been reported. Such reactivity is facilitated by a sodium alkoxide along with a corresponding trifluoroacetate ester, utilizing formation of sodium trifluoroacetate as a driving force for acetal formation. The usefulness of this protocol is demonstrated by its orthogonality with various acid-sensitive protecting groups and by good compatibility with functional groups, delivering synthetically useful acetals complementarily to the synthesis under acidic conditions from aldehydes and alcohols.

A practical in situ generation of the schwartz reagent. reduction of tertiary amides to aldehydes and hydrozirconation

A new, highly efficient in situ protocol (Cp2ZrCl2/LiAlH(OBu-t)3) is described for the generation of the Schwartz reagent which provides a convenient method for the amide to aldehyde reduction and the regioselective hydrozirconation-iodination of alkynes and alkenes. Highlighted are chemoselective reductions of benzamides derived by directed ortho metalation (DoM) chemistry, allowing the synthesis of valuable 1,2,3-substituted benzaldehydes. The single-step, three-component process proceeds in a very short reaction time, shows excellent functional group compatibility, and uses inexpensive and long-storage stable reducing reagents.

Schwartz Reagents: Methods of In Situ Generation and Use

Embodiments of the invention provide a method of using Schwartz Reagent, Cp2Zr(H)Cl, without accumulating or isolating it. Methods provide mixtures of Cp2ZrCl2, reductants that selectively reduce Cp2ZrCl2, and substrates. After reaction of Cp2ZrCl2 and the reductant, an intermediate reduction product is formed, apparently Schwartz Reagent. The in situ Schwartz Reagent then selectively reduces certain functional groups on the substrate. Substrates include tertiary amides, tertiary benzamides, aryl O-carbamates, and heteroaryl N-carbamates, which are reduced to aldehydes, benzaldehydes, aromatic alcohols, and heteroaromatics, respectively. Compared to prior methods, reagents are inexpensive and stable, reaction times are short, and reaction temperature in certain cases is conveniently room temperature. It has been estimated that using the in situ method described herein instead of synthesized or commercially obtained Schwartz Reagent provides a 50% reduction in cost.

PYRANONE COMPOUNDS USEFUL TO TREAT RETROVIRAL INFECTIONS

The present invention relates to compounds of formulae (I) and (II) which are pyran-2-ones, 5,6-dihydro-pyran-2-ones, 4-hydroxy-benzopyran-2-ones, 4-hydroxy-cycloalkyl[b]pyran-2-ones, and derivatives thereof, useful for inhibiting a retrovirus in a mammalian cell infected with said retrovirus, wherein R 10 and R 20 taken together are formulae (III) and (IV). STR1

Structure-based design of nonpeptidic HIV protease inhibitors: The sulfonamide-substituted cyelooctylpyranones

Recently, cyclooctylpyranone derivatives with m-carboxamide substituents (e.g. 2c) were identified as potent, nonpeptidic HIV protease inhibitors, but these compounds lacked significant antiviral activity in cell culture. Substitution of a sulfonamide group at the meta position, however, produces compounds with excellent HIV protease binding affinity and antiviral activity. Guided by an iterative structure-based drug design process, we have prepared and evaluated a number of these derivatives, which are readily available via a seven-step synthesis. A few of the most potent compounds were further evaluated for such characteristics as pharmacokinetics and toxicity in rats and dogs. From this work, the p-cyanophenyl sulfonamide derivative 35k emerged as a promising inhibitor, was selected for further development, and entered phase I clinical trials.

4-HYDROXY-BENZOPYRAN-2-ONES AND 4-HYDROXY-CYCLOALKYL[B]PYRAN-2-ONES USEFUL TO TREAT RETROVIRAL INFECTIONS

The present invention relates to compounds of formula I which are 4-hydroxy-benzopyran-2-ones and 4-hydroxy-cycloalkyl[b]pyran-2-ones useful for inhibiting a retrovirus in a mammalian cell infected with said retrovirus. STR1 Wherein R 10 and R 20 taken together are: STR2