494834-74-1

Upstream product

• 189635-63-0 methyl (2S)-3-[tert-butyl(diphenyl)silyl]oxy-2-hydroxypropanoate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 119879-74-2 (R)-1-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-propan-2-ol 
• 918868-38-9 (2S)-methyl 3-(tert-butyldiphenylsilyloxy)-2-methoxy-propionate 
• 494834-73-0 (2R)-3-(tert-butyldiphenyl-silyloxy)-2-methoxy-propan-1-ol 

Downstream Products

• 494834-75-2 (2S,3S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-ethyl]-3,5-dimethyl-2,3-dihydro-pyran-4-one 
• 848035-35-8 (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-4-methyl-hex-5-en-3-ol 
• 494834-77-4 6-[2-(tert-butyl-diphenyl-silanyloxy)-1-methoxy-ethyl]-3,5-dimethyl-5,6-dihydro-2H-pyran-2-ol 
• 494834-78-5 (Z)-(4R,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-ene-1,5-diol 
• 494834-79-6 (E)-Hepta-2,6-dienoic acid (Z)-(4R,5S,6S)-7-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6-methoxy-2,4-dimethyl-hept-2-enyl ester 
• 773860-01-8 (E)-Hepta-2,6-dienoic acid (Z)-(4R,5S,6S)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-5-methoxymethoxy-2,4-dimethyl-hept-2-enyl ester 
• 881031-81-8 C₃₃H₄₁NO₆Si 
• 918868-31-2 C₄₂H₇₂O₄Si₃ 
• 944823-25-0 C₃₉H₆₀O₅Si₂ 
• 944823-24-9 (Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester 
• 848035-32-5 C₂₉H₄₆O₄Si₂ 
• 848035-31-4 (2S,3S,4R)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenyl-silyloxy)-2-methoxy-4-methyl-hex-5-ene 
• 918868-37-8 hepta-2,6-dienoic acid 5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-1-[5-(2,6-dioxo-piperidin-4-yl)-1-methyl-2-oxo-pentyl]-6-methoxy-2,4-dimethyl-hept-2-enyl ester 
• 918868-35-6 4-[10-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-5,7,9-trimethyl-4-oxo-6-triethylsilanyloxy-dodec-7-enyl]-piperidine-2,6-dione 

Relevant academic research and scientific papers

Synthesis of migrastatin and its macrolide core

Migrastatin and its macrolactone subunit are potent antimetastatic agents. Both were synthesized by using a ring-closing metathesis (RCM) to establish the macrolactone core, and the control of the (Z)-trisubstituted double bond at C11-C12 was achieved by?

The migrastatin family: Discovery of potent cell migration inhibitors by chemical synthesis

The first asymmetric total synthesis of (+)-migrastatin (1), a macrolide natural product with antimetastatic properties, has been accomplished. Our concise and flexible approach utilized a Lewis acid-catalyzed diene aldehyde condensation (LACDAC) to install the three contiguous stereocenters and the trisubstituted (Z)-alkene of migrastatin (2 + 3 → 21). Construction of the two remaining stereocenters and incorporation of the glutarimide-containing side chain was achieved by an anti-selective aldol addition of propionyl oxazolidinone 28 to angelic aldehyde 27, followed by a Horner-Wadsworth-Emmons (HWE) coupling of 32 with glutarimide aldehyde 5. Finally, the assembly of the macrocycle was realized by a highly (E)-selective ring-closing metathesis (35 → 37). Utilizing the power of diverted total synthesis (DTS), a series of otherwise inaccessible analogues was prepared and evaluated for their potential as tumor cell migration inhibitors in several in vitro assays. These studies revealed a dramatic increase in activity when the natural motif was considerably simplified, presenting macrolactones 45 and 48, as well as macrolactam 55, macroketone 60, and CF3-alcohol 71 as promising anti-metastatic agents.

Synthesis of the macrolide core of migrastatin

A concise and efficient synthesis of the macrolactone core of migrastatin, a new natural product with potent anticancer properties, has been achieved. The key features of our synthetic strategy encompass a Lewis acid catalyzed diene aldehyde condensation