63598-31-2

Upstream product

• 6752-48-3 methyl 2-deoxy-4,6-O-benzylidene-α-D-ribo-hexopyranoside 
• 73395-15-0 methyl endo(phenyl)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 3162-96-7 methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 
• 126456-16-4 methyl 2,3-bis-O-<(trifluoromethyl)sulfonyl>-4,6-O-(phenylmethylene)-α-D-glucopyranoside 
• 71049-33-7 methyl 4,6-O-benzyliden-2-iodo-2-deoxy-α-D-altropyranoside 
• 91109-41-0 methyl-[O⁴,O⁶-((R)-benzylidene)-2-bromo-2-deoxy-α-D-altropyranoside] 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 66537-92-6 methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside 
• 65530-21-4 methyl 4,6-O-benzylidene-2,3-di-O-methanesulfonyl-α-D-glucopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 109-72-8 n-butyllithium 
• 194149-26-3 methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 6752-48-3 methyl 4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 

Downstream Products

• 122592-23-8 1-[(2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8Z)-ylidene]-propan-2-one 
• 126854-87-3 (2R,4aR,6S,7R,8aR)-7-[(S)-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-6-methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one 
• 66183-24-2 1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-erythro-hex-3-ulo-1-enitol 
• 78468-51-6 (S)-Fluoro-((2R,4aR,6S,8S,8aR)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-acetic acid methyl ester 
• 78468-50-5 methyl 4,6-O-benzylidene-2-deoxy-3-C-<(S)-(ethoxycarbonyl)fluoromethyl>α-D-ribo-hexopyranoside 
• 78468-50-5 methyl 4,6-O-benzylidene-2-deoxy-3-C-<(R)-(ethoxycarbonyl)fluoromethyl>α-D-ribo-hexopyranoside 
• 78468-51-6 (R)-Fluoro-((2R,4aR,6S,8S,8aR)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-acetic acid methyl ester 
• 78468-50-5 (R)-Fluoro-((2R,4aR,6S,8R,8aR)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-acetic acid ethyl ester 
• 122592-19-2 2-[(2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8Z)-ylidene]-propionic acid ethyl ester 
• 78086-67-6 methyl-4,6-O-benzylidene-2-desoxy-3-C-methyl-α-D-ribo-hexopyranoside 
• 72244-36-1 (2R,4aR,6S,8aS)-6-Methoxy-8-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 

Relevant academic research and scientific papers

Total syntheses of the non-peptide bradykinin B1 receptor antagonist velutinol a and its analogs, seco-pregnanes with a cage-like moiety

We describe here the syntheses of velutinol A (1) and the structurally similar compounds 24 sharing a highly oxygenated seco-pregnane cage-like structure. The synthesis of velutinol A (1, 15,16-seco-pregnane) features the highly regioselective construction of |14 silyl enol ether from 15-keto-21,22-diol, followed by stereoselective introduction of a sterically hindered β-hydroxy group at the C14 position by Rubottom oxidation. Prolonged reaction time and the use of an excess amount of mCPBA at this step allowed double Rubottom oxidation, enabling us to introduce the requisite hydroxy groups at the C14 and C16 positions in one pot. Subsequent oxidative cleavage of the C1516 bond, deprotection, and intramolecular acetalization allowed the concise total synthesis of velutinol A (1). Utilization of α,α-dihydroxy-ketone, the double Rubottom oxidation product, for formation of the ether F-ring by 5-exo-cyclization, and subsequent C1421 oxidative cleavage, effectively achieved the synthesis of pentalinonside-aglycon (2). Construction of the 14,15-seco-structures of two other analogs, argeloside aglycon (3) and illustrol (4), was achieved by BaeyerVilliger oxidation of 15(21)-keto derivatives. Introduction of the 20-oxo group potentially embedded in argeloside aglycon was accomplished by Wacker oxidation of |20, which was constructed by GriecoNishizawa syn-β-elimination of the C21-primary alcohol obtained by reduction of the BaeyerVilliger product. Intra-molecular double acetalization of the 15,16-dihydroxy-14,20-oxo derivative to form the cage-like structure of the DEF-rings required a moderately weak acid. This step was the key to accessing argeloside aglycon (3), as otherwise the easily aromatized β,γ-dihydroxyketone moiety was transformed to furan. Sharpless asymmetric dihydroxylation of |20 to set the C20 stereocenter, followed by intramolecular double acetalization, achieved the stereoselective synthesis of illustrol With all synthesized compounds, structural requirements of steroidal bradykinine B1 receptor antagonist would be revealed.

Efficient Two-Step Multifunctionalization of Substituted 2-Hydro-xyglycopyranosides

A straightforward route to diversely functionalized glycopyranosides is reported. 2,3-Enopyranosides, 2- and/or 3-azido-, 2-halopyranosides, and a hex-3-ulose, among other α- and β-glycopyranosides are easily obtained in good to excellent yields from 2-hydroxyglycopyranosides by means of a two-step process involving trifluoromethanesulfonation and subsequent treatment with the appropriate nucleophilic agent.

New mannose-derived ketones as organocatalysts for enantioselective dioxirane-mediated epoxidation of arylalkenes. Part 3: Chiral ketones from sugars

New d-arabino-hexopyranosid-3-uloses were synthesized by a simple method from mannopyranoside derivatives. The common skeleton possesses a tunable alkoxy group as steric sensor on carbon 2 of the sugar. The new ketones were employed in the dioxirane-mediated epoxidation of a range of trans- and trisubstituted arylalkenes giving enantiomeric excesses from low to good (30-90%). The effect of the size of the steric sensor on the enantioselectivity was also studied. The least bulky group (methoxy group) enhanced the stereoselectivity (up to 90% ee toward triphenylethylene).

Base-promoted reaction of methyl 4,6-O-benzylidene-3-deoxy-hexopyranosid-2- ulose and various arylamines

Reaction of methyl 4,6-O-benzylidene-3(2)-deoxy-hexopyranosid-2(3)-ulose (1) with various arylamines under Bargellini reaction conditions was investigated. A series of unique enaminoketones 3-12 was obtained unexpectedly under basic conditions in 52-72% y

Tagged hypervalent iodine reagents: A new purification concept based on ion exchange through SN2 substitution

(Chemical Equation Presented) The preparation of phenylsulfonate-tagged iodine(III) reagents as well as their use in a novel purification strategy for iodine(III)-promoted reactions is described. The concept is based on ion exchange and is initiated by an azide-promoted SN2-reaction at the alkyl sulfonate followed by trapping of the resulting aryl sulfonate anion with an ion-exchange resin. The concept is successfully proven for Ru-catalyzed oxidations of alcohols, the activation and glycosidatlon of thioglycosides, and the Suarez reaction of pyranoses.

m-iodosylbenzoic acid as a convenient recyclable reagent for highly efficient RuCl3-catalyzed oxidation of alcohols to carbonyl compounds

m-Iodosylbenzoic acid selectively oxidizes primary and secondary alcohols to the respective carbonyl compounds in the presence of RuCl3 (0.5 mol%) at room temperature in aqueous acetonitrile. Separation of pure products is conveniently achieved by scavenging any aryl iodide by ion exchange with IRA-900 (hydroxide form) or by simple extraction of the basic aqueous solution with water. The reduced form of the reagent, m-iodobenzoic acid, can be easily recovered from the ion-exchange resin or from the basic aqueous solution by simple acidification with HCl. Georg Thieme Verlag Stuttgart.

Synthesis of annelated pyranosides: a rapid and efficient entry to highly functionalized optically pure branched-pyrazoles

Pyrazolo-pyranosides prepared from methyl-2,3:4,6-di-O-benzylidene-α-d-mannopyranoside were functionalized to design new scaffolds suitable for peptidomimetic construction. Under certain acidic conditions, they undergo only pyranose ring-opening generatin

Enantioselective formal total synthesis of the antitumor macrolide bryostatin 7

A new enantioselective synthesis of Masamune's AB fragment (1) for bryostatin 7 is described. Key steps in the new route include a Meerwein-Ponndorf-Verley reduction to set the 0(7) stereocenter and an alkylative union between the dithiane 6 and iodide 5 to construct the C(9)-C(10) bond. Because we have previously published a synthesis of Masamune's C-ring phenyl sulfone 2, our new route to 1 constitutes a formal total synthesis of bryostatin 7; it also corrects the previously reported spectral data for 1 in CDCl3.

Synthesis of L-vancosamine derivatives from methyl α-D- mannopyranoside

Concise synthesis of L-vancosamine, the amino sugar constituent of vancomycin and other antibiotics, has been achieved. The key steps include (1) stereoselective addition of methylcerium reagent to oximino ether, and (2) stereoselective hydrogenation of 5

A simple and mild synthesis of a 4,5-cyclopropanated carbohydrate

The synthesis of a 4,5-cyclopropanated carbohydrate was achieved in five steps from methyl α-d-mannopyranoside under mild conditions that avoid the use of carbene chemistry.