159801-08-8

Basic information

• Product Name: methyl (3R)-4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate
• Synonyms: methyl (3R)-4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate
• CAS NO: 159801-08-8
• Molecular Weight: 372.536
• Mol File: 159801-08-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: methyl (3R)-4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (3R)-4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate(159801-08-8)
• EPA Substance Registry System: methyl (3R)-4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate(159801-08-8)

Safety Data

• Hazardous Substances Data: 159801-08-8(Hazardous Substances Data)

Upstream product

• 70681-41-3 (R)-dimethyl malate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 114819-45-3 (R)-methyl 3,4-dihydroxybutanoate 

Downstream Products

• 203249-99-4 (R)-3-Allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-butan-1-ol 
• 327027-74-7 4-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyric acid methyl ester 
• 1527512-84-0 (R)-7-(tert-butyldiphenylsilyloxy)-6-hydroxyhept-1-en-4-one 
• 1527512-87-3 (R)-2-(tert-butyldiphenylsilyloxy)-6-methyl-2H-pyran-4(3H)-one 
• 327027-75-8 (E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-5-(4-methoxy-benzyloxy)-hex-2-enoic acid methyl ester 
• 327027-71-4 (E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-5-(4-methoxy-benzyloxy)-hex-2-enal 
• 672296-58-1 4-(TERT-BUTYLDIPHENYLSILANYLOXY)-3-(4-METHOXYBENZYLOXY)-BUTYRALDEHYDE 
• 202268-20-0 (R)-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-N-methylbutanamide 
• 159801-11-3 (2S,3R) benzyl 2--4-<(tert-butyldiphenylsilyl)oxy>-3-hydroxybutanohydroxamate 
• 159801-12-4 (3S,4S) 1-(benzyloxy)-3--4-<(tert-butyldiphenylsilyloxy)methyl>-2-azetidinone 
• 168777-40-0 [(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-furan-2-yl]-acetaldehyde 
• 152518-69-9 (2R,4R)-1-(tert-Butyl-diphenyl-silanyloxy)-hex-5-ene-2,4-diol 
• 202268-21-1 (R)-6-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-hex-1-en-3-one 
• 168777-41-1 (2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-ol 

Relevant articles and documents

Concise total synthesis of (-)-erinapyrone b from d-(+)-malic acid

A convenient and facile enantioselective synthesis of (-)-erinapyrone B from commercially available D-(+)-malic acid has been achieved in seven steps. One of the key steps in this synthesis was the one-pot reaction of palladium(II)-mediated Wacker-type oxidative cyclization in the presence of a catalytic amount of p-toluenesulphonic acid (p-TsOH) which has been found to be effective for the preparation of enantiopure 2,3-dihydro-4H-pyran-4-one from the corresponding enantiopure β-hydroxyenone via enantio-enriched diketohydroxy intermediate.

Convergent synthesis of the C31-C46 domain of the phorboxazole natural products

A convergent synthesis of the C31-C46 domain of the phorboxazole natural products has been developed. This involved the preparation of a C39-C46 dienyl iodide and a C31-C37 aldehyde, followed by their CrCl2-mediated coupling and final installation of the C46 (E)-vinyl bromide via an alkyne hydrostannation-bromination sequence.

Macrocyclic bisindolylmaleimides: Synthesis by inter- and intramolecular alkylation

Macrocyclic bisindolylmaleimides 1-4 have been identified as competitive reversible inhibitors of PKC β1 and β2 and are being advanced to the clinic for evaluation as a treatment of retinopathy associated with diabetic complications. Highly convergent and stereoselective syntheses of 1-4 have been developed. The key synthetic step involves intermolecular alkylation of symmetrical bisindolylmaleimide 9 with chiral bisalkylating agent 8c and is amenable to the preparation of multikilogram quantities of these compounds. The synthetic sequence to 1, the most active the compound, proceeds in 11 steps and 26% overall yield (> 98% ee) from (R)-1-chloro-2,3-propanediol. No chromatographic purifications are required throughout the process and the final product is isolated in >97% purity after crystallization from DMF/MeOH. Synthesis of 1-4 by intramolecular alkylation proved less efficient, requiring 17 steps and affording 1-4 in lower overall yields of 6.0-8.5%.