258331-72-5

Upstream product

• 147726-64-5 5-[(triphenylmethyl)oxy]pentanol 
• 111-29-5 1 ,5-pentanediol 
• 76-83-5 trityl chloride 

Downstream Products

• 694-54-2 tetrahydro-2H-2-pyranol 
• 365441-14-1 (3R,4R)-3-Methyl-8-trityloxy-oct-1-en-4-ol 
• 122934-55-8 5-formylpentyl benzoate 
• 37854-36-7 benzoic acid 2-hydroxycyclohexyl ester 
• 365441-22-1 2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-8-trityloxy-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester 
• 365441-30-1 2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester 
• 365441-19-6 (1R,4S,5S,6R)-1-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decan-1-ol 
• 365441-18-5 (4S,5S,6R)-1-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decan-1-one 
• 627537-33-1 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-3,4-bis-benzyloxy-6-[(1R,4S,5R,6R)-1,4-dihydroxy-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decyl]-5-methyl-tetrahydro-pyran-2-ylmethyl ester 
• 365441-29-8 2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-4-(4-methoxy-benzyloxy)-3-methyl-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester 
• 627537-41-1 (1R,4S,5R,6R)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decane-1,4-diol 

Relevant academic research and scientific papers

Synthesis of AD-Dihydrodipyrrins Equipped with Latent Substituents of Native Chlorophylls and Bacteriochlorophylls

Native chlorophylls and bacteriochlorophylls share a common trans-substituted pyrroline ring D (17-propionic acid, 18-methyl), whereas diversity occurs in ring A particularly at the 3-position. Two dihydrodipyrrins equipped with native-like D-ring substit

Radical Cyclization Followed by the Fragmentation of Carbonyl Compounds: Effect of an α-Benzoyl Group

To study a recently developed radical cyclization reaction followed by a fragmentation process in more detail, a series of α-benzoyl carbonyl compounds were prepared, including precursors with aldehyde and ketone moieties. Initiated by tributyltin hydride

Formal Alder-ene reaction of a bicyclo[1.1.0]butane in the synthesis of the tricyclic quaternary ammonium core of daphniglaucins

A tricyclic substructure of the tetracyclic nitrogen core of the daphniglaucins was formed by an oxidative activation of the allyl side chain of a bicyclo[1.1.0]butylmethylamine, a spontaneous intramolecular formal Alder-ene reaction, and a selective cycl

Yb(OTf)3-catalyzed oxidation of alcohols with iodosylbenzene mediated by TEMPO

A rapid oxidation of primary and secondary alcohols using catalytic amounts of TEMPO and Yb(OTf)3 in combination with a stoichiometric amount of iodosylbenzene (PhIO) is described. This procedure operates at room temperature or above to afford carbonyl compounds in excellent yields without over-oxidation to carboxylic acids. Oxidation of primary alcohols in the presence of secondary alcohols proceeded with good selectivity. Georg Thieme Verlag Stuttgart.

New Antibacterial Agents Derived from the DNA Gyrase Inhibitor Cyclothialidine

Cyclothialidine (1, Ro 09-1437) is a potent DNA gyrase inhibitor that was isolated from Streptomyces filipinensis NR0484 and is a member of a new family of natural products. It acts by competitively inhibiting the ATPase activity exerted by the B subunit of DNA gyrase but barely exhibits any growth inhibitory activity against intact bacterial cells, presumably due to insufficient permeation of the cytoplasmic membrane. To explore the antibacterial potential of 1, we developed a flexible synthetic route allowing for the systematic modification of its structure. From a first set of analogues, structure-activity relationships (SAR) were established for different substitution patterns, and the 14-hydroxylated, bicyclic core (X) of 1 seemed to be the structural prerequisite for DNA gyrase inhibitory activity. The variation of the lactone ring size, however, revealed that activity can be found among 11- to 16-membered lactones, and even seco-analogues were shown to maintain some enzyme inhibitory properties, thereby reducing the minimal structural requirements to a rather simple, hydroxylated benzyl sulfide (XI). On the basis of these "minimal structures" a modification program afforded a number of inhibitors that showed in vitro activity against Gram-positive bacteria. The best activities were displayed by 14-membered lactones, and representatives of this subclass exhibit excellent and broad in vitro antibacterial activity against Gram-positive pathogens, including Staphylococcus aureus, Streptococcus pyogenes, and Enterococcus faecalis, and overcome resistance against clinically used drugs. By improving the pharmacokinetic properties of the most active compounds (94, 97), in particular by lowering their lipophilic properties, we were able to identify congeners of cyclothialidine (1) that showed efficacy in vivo.

Synthetic studies on altohyrtins (spongistatins): Synthesis of the C29-C44 (EF) portion

The C29-C44 portion of altohyrtins (spongistatins) has been prepared from 1,5-pentanediol and D-glucose in a stereoselective manner. The convergent synthesis relied on a coupling reaction of the C29-C37 vinyl bromide and the C38-C44 Weinreb amide, diaster