93367-10-3

Upstream product

• 128990-14-7 (S)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl4-methylbenzenesufonate 
• 57302-79-1 (3-hydroxymethyl-oxiranyl)-methanol 
• 116-11-0 2-Methoxypropene 
• 93367-08-9 Kalium-<4S-(R*,S*)>-α-hydroxy-2,2-dimethyl-1,3-dioxolan-4-acetat 
• 166249-17-8 methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxy-2-O-(p-toluenesulfonyl)butanoate 
• 84379-53-3 2-O-benzyl-3,4-O-isopropylidene-L-threitol 
• 119927-19-4 (2S)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyethyl 2,2-dimethylpropanoate 
• 136233-07-3 (+)-1-O-acetyl-3,4-O-isopropylidene-L-erythritol 
• 128142-59-6 Naphthalene-2-sulfonic acid (S)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-ethyl ester 
• 91274-05-4 (2S,3S)-1,2-O-isopropylidene-1,2,3,4-tetrol 
• 1379602-81-9 (2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanoic acid sodium salt 
• 58650-93-4 2,3-O-bis-methyl-5,6-O-isopropylidene-L-ascorbic acid 
• 126946-53-0 ethyl (2R,3S)-3,4-O-isopropylidene-2-p-toluenesulfonyl-3,4-dihydroxybutanoate 
• 136136-24-8 ((4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl butanoate 

Downstream Products

• 890532-91-9 Toluene-4-sulfonic acid (S)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-enyl ester 
• 890532-97-5 C₃₂H₄₄O₁₀S₂ 
• 890532-99-7 C₃₂H₄₆O₁₂S₂ 
• 532932-79-9 (4S)-4-[(1'S,3'Z)-4'-formyl-1'-phenylsulfonyloxy-3'-butenyl]-2,2-dimethyl-1,3-dioxolane 
• 532932-85-7 (2S,3R,4S,6R)-6-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4-methoxy-2-phenyltetrahydro-2H-pyran-3-ol 
• 532932-78-8 (4S)-4-[(1'S,3'Z)-5'-hydroxy-1'-phenylsulfonyloxy-3'-pentenyl]-2,2-dimethyl-1,3-dioxolane 
• 532932-84-6 (2S,3S,4R,6R)-6-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-3-methoxy-2-phenyltetrahydro-2H-pyran-4-ol 
• 532932-77-7 (4S)-4-[(1'S)-5'-hydroxy-1'-phenylsulfonyloxy-3'-pentynyl]-2,2-dimethyl-1,3-dioxolane 
• 532932-80-2 (4S)-4-[(1'S,3'Z,5'RS)-5'-hydroxy-5'-phenyl-1'-phenylsulfonyloxy-3'-pentenyl]-2,2-dimethyl-1,3-dioxolane 
• 532932-76-6 (4S)-4-[(1'S)-5'-(4-methoxybenzyloxy)-1'-phenylsulfonyloxy-3'-pentynyl]-2,2-dimethyl-1,3-dioxolane 
• 5754-34-7 2-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol 
• 128111-98-8 (2S,3S)-2-<2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybut-1-yl>-1,3-dithiane 
• 1372785-52-8 (S)-4-((S)-1-(4-methoxybenzyloxy)but-3-enyl)-2,2-dimethyl-1,3-dioxolane 
• 1372785-53-9 tert-butyl ((S)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(4-methoxybenzyloxy)propoxy)diphenylsilane 

Relevant academic research and scientific papers

An improved synthesis of the C15-C28 fragment of laulimalide

The C15-C28 fragment of the paclitaxel-like antimicrotubule agent laulimalide has been synthesized in 12 linear steps from known epoxide 5, with an overall yield of 16%. The methyldihydropyran ring of the side chain was efficiently prepared using ring-closing olefin metathesis chemistry. The 19,20-diol stereochemistry originates in starting material 7 and the side chain was appended using a Kocienski-modified Julia coupling.

Enantioselective synthesis of fatty acid amide hydrolase inhibitors with 1, 3-disubstituted butan-2-one scaffold

Fatty acid amide hydrolase is a key enzyme in the inactivation of the analgesic and anti-inflammatory endocannabinoid anandamide. Previously, the chiral compound 1-(1H-benzotriazol-1-yl)-3-(4-phenylphenoxy)butan-2-one was identified as a potent inhibitor of fatty acid amide hydrolase and is therefore of interest as a potential agent against pain and inflammation. Two different approaches for the enantioselective synthesis of fatty acid amide hydrolase inhibitors with a 1, 3-disubstituted butan-2-one scaffold were carried out. The first one uses the chiral epoxide 2-[1-(4-phenylphenoxy)ethyl]oxirane with an (R)- or (S)-configuration at the exocyclic stereocenter as central intermediates. These substances were obtained by separation of the non-stereoselectively synthesized epoxide into its racemic diastereomers by reversed phase chromatography followed by Jacobsen's hydrolytic kinetic resolution of each enantiomer with the (S)-configured oxirane ring. Furthermore, a chiral pool based enantioselective synthesis was developed. In that case, the starting compound for both target enantiomers was methyl 3, 4-O-isopropylidene-L-threonate. In comparison to the first approach, the chiral pool synthesis consisted of more steps, but generated the enantiomers with much better enantiomeric excess. Biological evaluation showed that the (R)-enantiomer inhibits isolated fatty acid amide hydrolase with a 200-fold higher activity than the (S)-enantiomer.

Packaging comprising forms of sodium salt of 4-tert-butyl-N-[4-chloro-2-(1-oxy-pyridine-4-carbonyl)-phenyl]-benzenesulfonamide

The invention relates to a packaging comprising a multitude (A) of at least 2 administration units comprising polymorphic trihydrated forms of sodium salt of 4-tert-butyl-N-[4-chloro-2-(1-oxy-pyridine-4-carbonyl)-phenyl]-benzenesulfonamide; or (B) of at least 2 administration units comprising polymorphic solvated or desolvated forms of sodium salt of 4-tert-butyl-N-[4-chloro-2-(1-oxy-pyridine-4-carbonyl)-phenyl]-benzenesulfonamide.

N- (6- ( (2R,3S) -3,4-DIHYDROXYBUTAN-2-YLOXY) -2- (4 - FLUOROBENZYLTHIO) PYRIMIDIN- 4 - YL) -3- METHYLAZETIDINE- 1 - SULFONAMIDE AS CHEMOKINE RECEPTOR MODULATOR

There is provided a compound which is (a) a pyrimidine sulfonamide of formula (I) or (b) a pharmaceutically acceptable salt thereof, crystalline forms of the compound, processes for obtaining the compound, pharmaceutical intermediates used in the manufacture of the compound, and pharmaceutical compositions containing the compound. The compound is useful in the treatment of a disease/condition in which modulation of chemokine receptor activity is beneficial.

First stereoselective total synthesis of panaxjapyne C

The first stereoselective total synthesis of polyacetylene panaxjapyne C is described. The key reactions include regioselective opening of the epoxide and Cadiot-Chodkiewicz cross-coupling reactions. l-Ascorbic acid was used as a chiral pool material for the construction of the both terminal acetylenes.

CRYSTALLINE FORMS OF N-[2-[[(2,3-DIFLUOROPHENYL)METHYL]THIO]-6--4-PYRIMIDINYL]-1-AZETIDINESULFONAMIDE

There is provided crystalline forms of N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-{[(1R,2S)-2,3-dihydroxy-1-methylpropyl]oxy}-4-pyrimidinyl]1-azetidinesulfon-amide anhydrate. Such compounds/forms may be useful in the treatment of a disease/condition in which modulation of chemokine receptor activity is beneficial.

From L-ascorbic acid to protease inhibitors: Practical synthesis of key chiral epoxide intermediates for aspartyl proteases

Efficient synthetic routes were developed to prepare a sizable amount (4-15 grams) of the chiral epoxides 4-6 as versatile intermediates for the synthesis of aspartyl protease inhibitors of therapeutic interest such as HIV protease and β-secretase. Oxidative cleavage of the C(2)-C(3) double bond of L-ascorbic acid followed by functional group manipulation led to the preparation of the epoxide 10, which was opened with an azide to yield a common aziridine intermediate 12. Through opening of the aziridine ring of 12 with either a carbon or a sulfur nucleophile, chiral epoxide precursors 4-6 could be prepared for various HIV protease inhibitors. Except for the final low melting epoxides 5 and 6, all intermediates were obtained as crystalline solids, thus the synthetic pathway can be easily applied to a large-scale synthesis of the chiral epoxides.

Total synthesis of (+)-obtusenyne

The stereoselective total synthesis of (+)-obtusenyne is described. The oxonene skeleton possessing trans-orientated alkyl substituents at the α,α′-positions was stereoselectively constructed via cyclization of the corresponding hydroxy epoxide promoted b

Stereoselective total synthesis of microcarpalide

A stereoselective total synthesis of microcarpalide using ring-closing metathesis (RCM) as a key step is reported. l-Ascorbic acid was used as a chiral pool material for the construction of the olefinic alcohol and an asymmetric aldol reaction provided the chiral precursor for the synthesis of olefinic acid.