412339-25-4

Upstream product

• 5427-29-2 methyl 2-hydroxy-4-benzyloxybenzoate 
• 52085-14-0 4-benzoxy-salicylaldehyde 
• 100-39-0 benzyl bromide 
• 95-01-2 2,4-Dihydroxybenzaldehyde 

Downstream Products

• 1029608-27-2 C₃₀H₂₈O₄ 
• 1072145-52-8 2-(5'-benzyloxy-2'-hydroxymethyl)phenoxy-1-(2'-benzyloxy-4'-methoxy-methylenoxy)phenylethanone 
• 57103-57-8 (+)-Glyceollin I 
• 1072145-55-1 (+)-4'-tert-butyldimethylsilyloxy-2',7-(dibenzyloxy)isoflavan-3,4-diol 
• 1322728-38-0 C₃₀H₂₈O₆ 
• 56701-24-7 vestitol 
• 1322728-39-1 C₃₀H₂₆O₄ 
• 1072145-56-2 2',7-dibenzyloxy-4'-hydroxy-isoflav-3-ene 
• 1072145-53-9 2',7-(dibenzyloxy)-4'-(methoxymethyloxy)isoflav-3-ene 
• 1072145-54-0 2',7-dibenzyloxy-4'-(tert-butyldimethylsilyloxy)isoflav-3-ene 
• 57103-57-8 (+/-)-glyceollin I 
• 52085-14-0 4-benzoxy-salicylaldehyde 

Relevant academic research and scientific papers

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.

Total syntheses of (±)-vestitol and bolusanthin III using a wittig strategy

An intramolecular Wittig olefination was utilized to -produce the key isoflav-3-ene intermediate needed to prepare (±)-vestitol and bolusanthin III in ca. 30% and 20% respective yields after eight steps. Georg Thieme Verlag Stuttgart ? New York.

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.

o-Quinone methide based approach to isoflavans: application to the total syntheses of equol, 3′-hydroxyequol and vestitol

A concise strategy is developed for the synthesis of isoflavans employing a Diels-Alder reaction between o-quinone methides and aryl-substituted enol ethers followed by reductive cleavage of the acetal group. The method is extended towards the total syntheses of equol, 3′-hydroxyequol and vestitol.

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.

ORGANIC COMPOUNDS

Compounds of the formula are inhibitors of protein tyrosine phosphatases (PTPases) and, thus, may be employed for the treatment of conditions mediated by PTPase activity. The compounds of the present invention may also be employed as inhibitors of other enzymes characterized with a phosphotyrosine binding region such as the SH2 domain. Accordingly, the compounds of formula (I) may be employed for prevention and/or treatment of insulin resistance associated with obesity, glucose intolerance, diabetes mellitus, hypertension and ischemic diseases of the large and small blood vessels, conditions that accompany type-2 diabetes, including hyperlipidemia, hypertriglyceridemia, atherosclerosis, vascular restenosis, irritable bowel syndrome, pancreatitis, adipose cell tumors and carcinomas such as liposarcoma, dyslipidemia, and other disorders where insulin resistance is indicated. In addition, the compounds of the present invention may be employed to treat and/or prevent cancer (such as prostate or breast cancer), osteoporosis, neurodegenerative and infectious diseases, and diseases involving inflammation and the immune system.