BUTANOIC ACID, 3-HYDROXY-4-(TRIPHENYLMETHOXY)-, METHYL ESTER, (R)

Base Information

• Chemical Name: BUTANOIC ACID, 3-HYDROXY-4-(TRIPHENYLMETHOXY)-, METHYL ESTER, (R)
• CAS No.: 144754-24-5
• Molecular Formula: C24H24 O4
• Molecular Weight: 376.452
• Mol file: 144754-24-5.mol

Synonyms:Butanoicacid, 3-hydroxy-4-(triphenylmethoxy)-, methyl ester, (R)-

Chemical Property of BUTANOIC ACID, 3-HYDROXY-4-(TRIPHENYLMETHOXY)-, METHYL ESTER, (R)

Chemical Property:

• Boiling Point: 536.0±50.0 °C(Predicted)
• PKA: 12.98±0.20(Predicted)
• PSA: 55.76000
• Density: 1.165±0.06 g/cm3(Predicted)
• LogP: 3.91910

Purity/Quality:

99% ^*data from raw suppliers

METHYL-(R)-3-HYDROXY-4-TRITYLOXY-BUTANOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BUTANOIC ACID, 3-HYDROXY-4-(TRIPHENYLMETHOXY)-, METHYL ESTER, (R)

There total 6 articles about BUTANOIC ACID, 3-HYDROXY-4-(TRIPHENYLMETHOXY)-, METHYL ESTER, (R) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

trityl chloride (76-83-5) + methyl (3S)-3,4-dihydroxybutyrate (90414-36-1) → (S)-methyl 3-hydroxy-4-(trityloxy)butanoate (144754-24-5,113240-53-2)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; regioselective reaction;

DOI:10.3762/bjoc.17.99

Reference yield: 87.0%

trityl chloride (76-83-5) + (R)-methyl 3,4-dihydroxybutanoate (114819-45-3) → methyl (R)-3-hydroxy-4-(triphenylmethyl)oxybutanoate (144754-24-5)

Guidance literature:

With dmap; triethylamine; In N,N-dimethyl-formamide; at 65 ℃;

DOI:10.1016/S0040-4039(97)10660-8

Reference yield:

(R)-dimethyl malate (70681-41-3) → methyl (R)-3-hydroxy-4-(triphenylmethyl)oxybutanoate (144754-24-5)

Guidance literature:

Multi-step reaction with 2 steps

1: BH₃*SMe₂, NaBH₄ / tetrahydrofuran / Ambient temperature

2: 4-DMAP, NEt₃ / dimethylformamide / Ambient temperature

With dmap; sodium tetrahydroborate; dimethylsulfide borane complex; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(99)00069-5

upstream raw materials:

trityl chloride

(R)-methyl 3,4-dihydroxybutanoate

(R)-dimethyl malate

1-O-methyl (3R)-3-hydroxysuccinate

Downstream raw materials:

1,1-Dimethylethyl (S)-5-hydroxy-3-oxo-6-(triphenylmethoxy)hexanoate

methyl (S)-3-(tert-butyldimethylsilanyloxy)-4-(trityloxy)butanoate

(3R)-3-(tert-butyldimethylsilanyloxy)-4-trityloxybutyraldehyde

(+)-(R)-3-((tert-butyldimethylsilyl)oxy)-4-(trityloxy)butan-1-ol

Refernces

• 1、 Dias, Luiz C.,De Lucca, Emilio C.. "Total Synthesis of (-)-Marinisporolide C". . p. 3019 - 3045. Retrieved 2017/03/23.
• 2、 White, James D.,Lincoln, Christopher M.,Yang, Jongtae,Martin, William H. C.,Chan, David B.. "Total synthesis of solandelactones A, B, E, and F exploiting a tandem petasis-claisen lactonization strategy". . p. 4139 - 4150. Retrieved 2008/09/20.