1072145-53-9

Upstream product

• 1072145-52-8 2-(5'-benzyloxy-2'-hydroxymethyl)phenoxy-1-(2'-benzyloxy-4'-methoxy-methylenoxy)phenylethanone 
• 1575479-23-0 C₁₅H₁₇BO₅ 
• 1575479-05-8 C₁₆H₁₃ClO₂ 
• 3769-41-3 3-Benzyloxyphenol 
• 6626-15-9 4-Bromoresorcinol 
• 70120-18-2 3-(benzyloxy)-4-bromophenol 
• 1072145-51-7 1-(2'-benzyloxy-4'-methoxymethylenoxy)phenyl-2-iodoethanone 
• 1026107-41-4 2-benzyloxy-4-methoxymethylenoxyacetophenone 
• 412339-25-4 4-benzyloxy-salicylalcohol 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 65490-08-6 2-hydroxy-4-(methoxymethoxy)acetophenone 
• 52085-14-0 4-benzoxy-salicylaldehyde 
• 100-39-0 benzyl bromide 
• 95-01-2 2,4-Dihydroxybenzaldehyde 

Downstream Products

• 1072145-56-2 2',7-dibenzyloxy-4'-hydroxy-isoflav-3-ene 
• 57103-57-8 (+/-)-glyceollin I 
• 1072145-54-0 2',7-dibenzyloxy-4'-(tert-butyldimethylsilyloxy)isoflav-3-ene 
• 1072145-55-1 (+)-4'-tert-butyldimethylsilyloxy-2',7-(dibenzyloxy)isoflavan-3,4-diol 
• 57103-57-8 (+)-Glyceollin I 

Relevant academic research and scientific papers

Formal synthesis of soybean phytoalexin glyceollin i

Glyceollins are well-known phytoalexins isolated from soybean (Glycine max). An efficient three-step synthesis was developed for the preparation of the key intermediate in Khupse's glyceollin I synthesis. Claisen rearrangement-cyclization cascade reaction

METHODS FOR SYNTHESIZING GLYCINOLS, GLYCEOLLINS I AND II, COMPOSITIONS OF SELECTED INTERMEDIATES, AND THERAPEUTIC USES THEREOF

Two distinct methods are disclosed and claimed for synthesizing glyceollin I plus glyceollin II as a mixture and as their pure forms. Stereochemical isomers and various synthetic intermediates are also synthesized and claimed for their novel compositions of matter. All compounds and their mixtures are claimed for use in formulations that are useful to treat or prevent cancer, or that have utility as selective estrogen receptor modulators, such formulations including enhanced or medical foods, dietary supplements and ethical pharmaceutical agents.

Multigram synthesis of glyceollin i

Scaled-up procedures and preparation of glyceollin I in multigram quantities are described. The synthesis features construction of a cis-fused ring system in high enantiomeric excess after Sharpless asymmetric dihydroxylation of a key intermediate that is initially produced by an intramolecular Wittig reaction to afford the requisite alkene while simultaneously forming the first ring. The overall yield is 12% after 11 steps.

Total syntheses of racemic and natural glycinol

Total syntheses of racemic and (-)-glycinol (1) are described. A Wittig reaction produced the isoflav-3-ene from which a Sharpless dihydroxylation introduced either the racemic or enantiomeric 6a-hydroxy group. A 5.5% overall yield of racemic material was obtained after 12 steps. A method was devised for a one-pot switch of protecting groups masking a sensitive resorcinolic para-functionality, and conditions were optimized to prompt spontaneous closure of the pterocarpanolic dihydrofuran upon subsequent exposure of its ortho-functionality. These improvements eliminated two steps and increased the overall yield to 9.8% during production of the natural enantiomer.

Total syntheses of racemic, natural (-) and unnatural (+) glyceollin I

(Chemical Equation Presented) The first total syntheses of racemic glyceollin I and its enantiomers are described. A Wittig approach was utilized as an entry to the appropriately substituted isoflav-3-ene so that an osmium tetroxide mediated asymmetric dihydroxylation could be deployed for stereospecific Introduction of the 6a-hydroxy group. While using triphenylphosphine hydrobromide, a novel method was found for gently removing MOM from protected phenolic hydroxyl groups present within sensitive systems.