(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal

Base Information

• Chemical Name: (2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal
• CAS No.: 872369-17-0
• Molecular Formula: C₁₉H₃₂O₃Si
• Molecular Weight: 336.547
• Mol file: 872369-17-0.mol

Synonyms:(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal

Chemical Property of (2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal

There total 11 articles about (2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal 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: 95.0%

(?)-(2S,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentan-1-ol (872369-16-9) → (2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal (872369-17-0)

Guidance literature:

DOI:10.1016/j.tetlet.2006.06.173

Reference yield: 86.0%

C20H34O2Si → (2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal (872369-17-0)

Guidance literature:

C₂₀H₃₄O₂Si; With ozone; In methanol; dichloromethane; at -78 ℃; Inert atmosphere;

With triphenylphosphine; Inert atmosphere;

DOI:10.1038/ja.2015.148

Reference yield: 78.0%

(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentan-1-one (1584664-36-7) → (2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal (872369-17-0)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetasy.2014.01.004

upstream raw materials:

(?)-(2S,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentan-1-ol

(2R,3S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methyl-pentan-1-one

(2R,3S)-5-Benzyloxy-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2-methyl-pentan-1-one

(-)-(R)-4-benzyl-3-[(2R,3S)-5-(benzyloxy)-3-hydroxy-2-methylpentanoyl]-1,3-oxazolidin-2-one

Downstream raw materials:

((3S,4S)-1-(benzyloxy)-4-methyloct-5-en-3-yloxy)(tert-butyldimethylsilane)

(2S,3R,4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-vinyl-heptane-1,3-diol

{(1S,2S)-1-(2-Benzyloxy-ethyl)-2-[(4R,5S)-2-(4-methoxy-phenyl)-5-vinyl-[1,3]dioxan-4-yl]-propoxy}-tert-butyl-dimethyl-silane

(2S,3R,4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-methyl-2-vinyl-heptan-1-ol

Refernces

• 1、 Itagaki, Tomohiro,Kawamata, Ayano,Takeuchi, Miho,Hamada, Keisuke,Iwabuchi, Yoshiharu,Eguchi, Tadashi,Kudo, Fumitaka,Usui, Takeo,Kanoh, Naoki. "Synthesis and structure-activity relationship study of FD-891: Importance of the side chain and C8-C9 epoxide for cytotoxic activity against cancer cells". . p. 287 - 293. Retrieved 2016/05/09.
• 2、 Chandrasekhar, Srivari,Sathish, Kurapati,Reddy, Gangireddy Pavan Kumar,Mainkar, Prathama S.. "Total syntheses of arenamides A, B and C". . p. 348 - 355. Retrieved 2014/04/03.