ethyl (2S,3R)-3,5-[(R)-benzylidenedioxy]-2-methyl-2-methylthiopentanoate

Base Information

• Chemical Name: ethyl (2S,3R)-3,5-[(R)-benzylidenedioxy]-2-methyl-2-methylthiopentanoate
• CAS No.: 668421-72-5
• Molecular Formula: C₁₆H₂₂O₄S
• Molecular Weight: 310.414
• Mol file: 668421-72-5.mol

Synonyms:ethyl (2S,3R)-3,5-[(R)-benzylidenedioxy]-2-methyl-2-methylthiopentanoate

Chemical Property of ethyl (2S,3R)-3,5-[(R)-benzylidenedioxy]-2-methyl-2-methylthiopentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2S,3R)-3,5-[(R)-benzylidenedioxy]-2-methyl-2-methylthiopentanoate

There total 3 articles about ethyl (2S,3R)-3,5-[(R)-benzylidenedioxy]-2-methyl-2-methylthiopentanoate 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:

(diethoxymethyl)benzene (774-48-1) + ethyl (2S,3R)-3-hydroxy-5-(triisopropylsiloxy)-2-methyl-2-methylthiopentanoate (668421-71-4) → ethyl (2S,3R)-3,5-[(R)-benzylidenedioxy]-2-methyl-2-methylthiopentanoate (668421-72-5)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 25 ℃; for 27h;

DOI:10.1002/chem.200500417

Reference yield:

(E/Z)-1-ethoxy-1-(trimethylsiloxy)-2-methylthiopropene (1051925-20-2) → ethyl (2S,3R)-3,5-[(R)-benzylidenedioxy]-2-methyl-2-methylthiopentanoate (668421-72-5)

Guidance literature:

Multi-step reaction with 2 steps

1: (S)-1-methyl-2-(1-naphthylaminomethyl)pyrrolidine; Sn(OTf)2; nBu₃SnF / CH₂Cl₂ / 14 h / -78 °C

2: p-TsOH / CH₂Cl₂ / 27 h / 25 °C

With tin(II) trifluoromethanesulfonate; (S)-1-methyl-2-(1-naphthylaminomethyl)pyrrolidine; tributyltin fluoride; toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1002/chem.200500417

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) + ethyl (2S,3R)-3-hydroxy-5-(triisopropylsiloxy)-2-methyl-2-methylthiopentanoate (668421-71-4) → ethyl (2S,3R)-3,5-[(R)-benzylidenedioxy]-2-methyl-2-methylthiopentanoate (668421-72-5)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 0 ℃;

DOI:10.1016/j.tetlet.2003.10.213

upstream raw materials:

benzaldehyde dimethyl acetal

ethyl (2S,3R)-3-hydroxy-5-(triisopropylsiloxy)-2-methyl-2-methylthiopentanoate

(diethoxymethyl)benzene

(E/Z)-1-ethoxy-1-(trimethylsiloxy)-2-methylthiopropene

Downstream raw materials:

(3R,4S,7S,8R,13S)-3-benzyloxy-13-(t-butyldimethylsiloxy)-9-hydroxy-4,8,10,14-tetramethyl-(E)-10-pentadecen-7-olide

(3R,4S,7S,8S,13S)-3-benzyloxy-13-(t-butyldimethylsiloxy)-4,8,10,14-tetramethyl-9-oxo-(E)-10-pentadecen-7-olide

(3R,4S,7S,8S,13S)-3-benzyloxy-13-hydroxy-4,8,10,14-tetramethyl-9-oxo-(E)-10-pentadecen-7-olide

(2R,3S,6S,7R)-7-benzyloxy-9-(t-butyldimethylsiloxy)-1-(t-butyldiphenylsiloxy)-3-(p-methoxybenzyloxy)-2,6-dimethyl-cis-4-nonene