116386-63-1

Basic information

• Product Name: (E)-2-Methyl-3-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2-propenal
• Synonyms: (E)-2-Methyl-3-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2-propenal
• CAS NO: 116386-63-1
• Molecular Weight: 354.605
• Mol File: 116386-63-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (E)-2-Methyl-3-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2-propenal(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-Methyl-3-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2-propenal(116386-63-1)
• EPA Substance Registry System: (E)-2-Methyl-3-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2-propenal(116386-63-1)

Safety Data

• Hazardous Substances Data: 116386-63-1(Hazardous Substances Data)

Upstream product

• 116386-61-9 (1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexanecarboxaldehyde 
• 99405-12-6 α-(triethylsilyl)propionaldehydr tert-butylimine 
• 116409-60-0 Imidazole-1-carbothioic acid O-((1R,2S,6R,8R)-9-oxo-4-thioxo-3,5,10-trioxa-tricyclo[6.2.1.0^2,6]undec-8-yl) ester 
• 127126-09-4 (1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexanecarboxylic acid methoxy-methyl-amide 
• 116386-60-8 (1R,3R,4R)-3-Hydroxy-4-triisopropylsilanyloxy-cyclohexanecarboxylic acid methoxy-methyl-amide 
• 127062-21-9 (1R,4R,5R)-4-Triisopropylsilanyloxy-6-oxa-bicyclo[3.2.1]octan-7-one 
• 116409-61-1 (1R,2S,6R)-4-Thioxo-3,5,10-trioxa-tricyclo[6.2.1.0^2,6]undecan-9-one 
• 116498-92-1 (1R,4R,5R)-4-hydroxy-6-oxabicyclo[3.2.1]octan-7-one 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 128684-90-2 Methyl (1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexanecarboxylate 
• 128684-89-9 (1R,3R,4R) methyl 4-hydroxy-3-methoxy-1-cyclohexanecarboxylate 
• 128684-88-8 methyl (1R,3R)-3-methoxycyclohex-4-enecarboxylate 
• 109667-78-9 N-(4-chloro-7-oxo-6-oxabicyclo[3.2.1]octan-3-yl)acetamide 
• 54911-89-6 (1R,5R)-methyl-5-hydroxycyclohex-3-enecarboxylate 

Downstream Products

• 116386-64-2 (S)-3-[(E)-(2S,3S)-3-Hydroxy-5-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-pent-4-enoyl]-4-isopropyl-oxazolidin-2-one 
• 126788-80-5 (E)-(2S,3S)-3-Hydroxy-5-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-pent-4-enoic acid methoxy-methyl-amide 
• 116386-65-3 (E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enal 
• 126788-81-6 (E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enoic acid methoxy-methyl-amide 
• 126788-84-9 (E)-(3S,4R,5S)-3-Hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoic acid methoxy-methyl-amide 
• 116386-67-5 (E)-(3S,4R,5S)-7-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-3-triisopropylsilanyloxy-hept-6-enal 
• 126788-85-0 (E)-(3S,4R,5S)-7-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-3-triisopropylsilanyloxy-hept-6-enoic acid methoxy-methyl-amide 
• 126788-83-8 (S)-4-Benzyl-3-[(E)-(3S,4R,5S)-3-hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoyl]-oxazolidin-2-one 
• 126788-82-7 (S)-4-Benzyl-3-[(E)-(2S,3R,4R,5S)-2-chloro-3-hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoyl]-oxazolidin-2-one 
• 116386-66-4 (E)-(3S,4R,5S)-3-Hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester 
• 148235-86-3 (S)-1-(Methoxy-methyl-aminooxalyl)-piperidine-2-carboxylic acid (1S,2R)-1-[(E)-2-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-1-methyl-vinyl]-2-methyl-but-3-enyl ester 

Relevant articles and documents

Synthesis of a C22-34 subunit of the immunosuppressant FK-506

A new route to the C22-34 subunit of FK-506 was developed. A highly diastereoselective Diels-Alder reaction of 1,3-butadiene with the bis-acrylate of (R,R)-hydrobenzoin and subsequent saponification provided the cyclohexenecarboxylic acid 6.4 of 95% ee. Elaboration to the enal 9.2 was effected by known transformations. Enal 9.2 underwent diastereoselective and enantiospecific S(E)2' addition of allenyl stannane (S)-3.9 affording the homopropargylic alcohol 9.3 as an 85:15 syn/anti mixture. The PMB ether 9.5 was converted to the known benzylidene derivative 10.4 by sequential treatment with Red-Al, epoxidation, a second reduction with Red-Al, and oxidative benzylidene formation with DDQ.

DIASTEREOSPECIFIC, NON-RACEMIC SYNTHESIS OF THE C.20-C.34 SEGMENT OF THE NOVEL IMMUNOSUPPRESSANT FK-506

An efficient stereocontrolled route to construct the C.20-C.34 moiety of FK-506 is described.