61042-29-3

Upstream product

• 908093-98-1 diazodiphenylmethane 
• 5350-57-2 benzophenone hydrazone 
• 603-35-0 triphenylphosphine 
• 79287-72-2 diphenylmethyl bromoacetate 
• 91-01-0 1,1-Diphenylmethanol 

Downstream Products

• 61075-45-4 3t-[(6R)-3-acetoxymethyl-8-oxo-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-2-yl]-acrylic acid benzhydryl ester 
• 175652-37-6 (E)-(4S,5R,6R,7R)-4,5,6,7,8-Pentahydroxy-oct-2-enoic acid benzhydryl ester 
• 175652-39-8 (E)-(4S,5R,6S,7R)-4,5,6,7,8-Pentahydroxy-oct-2-enoic acid benzhydryl ester 
• 495-71-6 phenacylacetophenone 
• 352462-27-2 diphenylmethyl (E)-2,3-dideoxy-D-arabino-hept-2-enonate 
• 352462-29-4 diphenylmethyl (E)-2,3-dideoxy-D-xylo-hept-2-enonate 

Relevant academic research and scientific papers

Phosphine-Catalyzed Domino β/γ-Additions of Benzofuranones with Allenoates: A Method for Unsymmetrical 3,3-Disubstituted Benzofuranones

A phosphine-catalyzed domino process of benzofuranones with allenoates has been developed which furnishes highly functionalized unsymmetrical 3,3-disubstituted benzofuranones in synthetically useful yields. The mechanism for the transformation is a tandem β-umpolung/γ-umpolung process.

A convenient route to higher sugars by two-carbon chain elongation using Wittig/dihydroxylation reactions

The combination of a Wittig olefination and a dihydroxylation reaction constitutes a facile synthetic protocol for the transformation of unprotected carbohydrates into higher sugars. The Wittig reaction is carried out with tert-butyl or diphenylmethyl ester stabilized phosphoranes to give (E)-configured α,β-unsaturated esters as the only products in most cases. These are dihydroxylated in a diastereoselective fashion using OsO4/NMO. The stereochemical outcome in the dihydroxylation follows Kishi's empirical rule and gives high diastereoselectivity (5:1-8:1) when starting from sugars with the 2,3-threo configuration. When starting from sugars with the 2,3-erythro configuration, the diastereoselectivity in the dihydroxylation is low (2:1-2.5:1). As a result, the Wittig/dihydroxylation protocol is most effective for producing higher sugars with the galacto configuration at the reducing end. The two steps can either be carried out individually or, more efficiently, as a one-pot procedure.

Wittig chain extension of unprotected carbohydrates: Formation of carbohydrate-derived α,β-unsaturated esters

Unprotected carbohydrates react with Wittig reagents 6 and 7 to give unsaturated esters. This homologation has been used to prepare an intermediate (18) previously employed in a synthesis of Kdo (19).

3-(Substituted) vinyl cephalosporins

New 3-(substituted) vinyl cephalosporin compounds, e.g., 3-(2'-ethoxycarbonylvinyl)-7-phenoxyacetamido-3-cephem-4-carboxylic acid, which are useful as antibiotics, and 3-(substituted) vinyl cephalosporin compounds which are useful as intermediates in preparing antibiotic substances.