92973-40-5

Usage

Uses

Used to prepare a dihydrofuran substrate in the total synthesis of (-)-echinosporin.

InChI:InChI=1/C8H14O5/c1-8(2)12-4-5(13-8)6(9)7(10)11-3/h5-6,9H,4H2,1-3H3/t5-,6+/m0/s1

Upstream product

• 58650-92-3 5,6-O-isopropylidene-3-O-methyl-L-ascorbic acid 
• 98733-24-5 calcium bis[(2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)acetate] 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 15042-01-0 5,6-O-isopropylidene-L-ascorbic acid 
• 67-64-1 acetone 
• 50-81-7 ascorbic acid 
• 186581-53-3 diazomethane 
• 92973-39-2 O³,O⁴-(1-methylethylidene)-L-threonic acid 
• 77-76-9 2,2-dimethoxy-propane 
• 1379602-81-9 (2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanoic acid sodium salt 
• 50271-42-6 5,6-O-isopropylidene-D-isoascorbic acid 
• 93367-08-9 Kalium-<4S-(R*,S*)>-α-hydroxy-2,2-dimethyl-1,3-dioxolan-4-acetat 

Downstream Products

• 130258-73-0 Methyl 3,4-Isopropylidenedioxy-2-(tert-butyldiphenylsiloxy)butanoate 
• 116556-67-3 Methyl 3,4-O-isopropylidene-2-O-phenoxythiocarbonyl-L-threonate 
• 94482-90-3 (S)-2-(2',2'-Dimethyl-1',3'-dioxolan-4'-yl)-2-oxoethylbenzoate 
• 639840-10-1 methyl (2R,3S)-2-(4-bromobenzyloxy)-3,4-dihydroxy-3,4-O-isopropylidene-butyrate 
• 166249-17-8 methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxy-2-O-(p-toluenesulfonyl)butanoate 
• 128056-99-5 (S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate 
• 117399-58-3 (1S)-2-(benzyloxy)-1-[(4S)-2,2-dimethyl-1,3-dioxolane-4-yl]-ethan-1-ol 
• 115890-33-0 3-azido-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-D-erythritol 
• 170936-50-2 Toluene-4-sulfonic acid (S)-2-benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester 
• 93367-10-3 (2S,3S)-3,4-epoxy-1,2-di-O-isopropylidenebutane-1,2-diol 
• 143884-03-1 (2S,3S)-1,2-O-isopropylidene-3-tert-butyldiphenylsiloxy-10-undecene-1,2,3-triol 
• 143884-05-3 (2S,3S)-1,2-O-isopropylidene-3-tert-butyldiphenylsiloxyundecane-1,2,3,10-tetraol 
• 143884-04-2 (2S,3S)-10,11-epoxy-1,2-O-isopropylidene-3-tert-butyldiphenylsiloxyundecane-1,2,3-triol 
• 143884-06-4 (2S,3S)-10-acetoxy-1,2-O-isopropylidene-3-tert-butyldiphenylsiloxyundecane-1,2,3,10-tetraol 

Relevant academic research and scientific papers

Synthesis of a diastereomer of the marine macrolide lytophilippine A

The synthesis of a diastereomer of lytophilippine A required 22 longest linear steps using known building blocks. Cross-metathesis/asymmetric aldol addition and regioselective esterification/ring-closing metathesis served as efficient combi tools for scaffold construction. Detailed NMR investigations in different solvent (systems) provide evidence for a deep-seated configurational misassignment of the molecule named lytophilippine A.

Design, synthesis and biological evaluation of C(4) substituted monobactams as antibacterial agents against multidrug-resistant Gram-negative bacteria

A series of novel pyridone conjugated monobactams with various substituents at the (4) position were synthesized and evaluated for their antibacterial activities against a panel of multidrug-resistant (MDR) Gram-negative bacteria in vitro. Compounds 46d, 54 and 75e displayed good to moderate activities against P. aeruginosa, among which the activity of 75e against P. aeruginosa was comparable to that of BAL30072 under iron limitation condition. Compounds 35, 46d, 54, 56a, 56c and 56d exhibited good to excellent antibacterial activities against E. coli and K. pneumoniae, which were comparable or superior to that of BAL30072. In vitro liver microsomal stability was further evaluated and the results manifested that Compounds 35, 46d and 54 were metabolically stable in human liver microsomes.

Synthetic study of cnicin: Synthesis of the side chain and its esterification

Cnicin is a germacranolide sesquiterpene lactone that possesses potent inhibitory activity against the protozoan parasite Trypanosoma brucei, which causes human African trypanosomiasis (HAT). Although cnicin has an interesting structure and attractive biological activity, synthetic studies of cnicin have not yet been reported. This report describes the synthesis of the protected side chain carboxylic acid moiety at C8 of cnicin via two routes starting from L-ascorbic acid. In addition, esterification between the synthetic side chain and salonitenolide derivative, which can be achieved via hydrolysis of cnicin and protection of the primary alcohol, was conducted. Thus, a semi-synthesis of cnicin was achieved.

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.

PROCESS FOR THE PREPARATION OF [(1 S,2R)-3-[[(4-AMINOPHENYL)SULFONYL] (2-METHYLPROPYL)AMINO]-2-HYDROXY-1 -(PHENYLMETHYL)PROPYL]-CARBAMIC ACID (3R,3AS,6AR)HEXAHYDRO FURO[2,3-B]FURAN-3-YL ESTER AND ITS AMORPHOUS FORM

The present invention relates to an improved process for the preparation of [(1 S,2R)-3-[ [(4-aminophenyl)sulfonyl] (2-methylpropyl)amino]-2-hydroxy- 1 -(phenylmethyl)propyl] - carbamic acid (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl ester compound of formula- 1 represented by the following structural formula:

A cross-metathesis approach to the synthesis of (+)-phomopsolide B

Abstract The synthesis of phomopsolide B has been achieved using an olefin cross-metathesis (CM) reaction as key step. Two metathesis partners, enediol and 5-hydroxy vinyl lactone were prepared from l-ascorbic acid. This is the first report of using 5-hyd

Stereoselective total synthesis of both (6R,9R,10S,7E)- and (6S,9R,10S,7E)-epimers of oxylipin (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid

An asymmetric synthesis of both the stereoisomers (2a & 2b) of the structure 2 proposed for (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid, an immunostimulant oxylipin from the n-butanol extract of the corms of Dracontium loretense, has been accomplished. The key steps involved are using Jacobsen's hydrolytic kinetic resolution (HKR), Julia-Kocienski olefination, regioselective epoxide ring opening and Wittig olefination. The configuration (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid was established as 2a from comparison of NMR data, HPLC analysis and [α]D values of naturally derived (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid, and comparison with the synthetic diastereomers 2a and 2b.

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.

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.