(2R,3S,4R)-3-tert-butyldiphenylsilyloxy-4,5-cyclohexylidenedioxy-2-methylpentanal

Base Information

• Chemical Name: (2R,3S,4R)-3-tert-butyldiphenylsilyloxy-4,5-cyclohexylidenedioxy-2-methylpentanal
• CAS No.: 1315500-59-4
• Molecular Formula: C₂₈H₃₈O₄Si
• Molecular Weight: 466.693
• Mol file: 1315500-59-4.mol

Synonyms:(2R,3S,4R)-3-tert-butyldiphenylsilyloxy-4,5-cyclohexylidenedioxy-2-methylpentanal

Chemical Property of (2R,3S,4R)-3-tert-butyldiphenylsilyloxy-4,5-cyclohexylidenedioxy-2-methylpentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-3-tert-butyldiphenylsilyloxy-4,5-cyclohexylidenedioxy-2-methylpentanal

There total 3 articles about (2R,3S,4R)-3-tert-butyldiphenylsilyloxy-4,5-cyclohexylidenedioxy-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: 81.0%

(3S,4S,5R)-4-tert-butyldiphenylsilyloxy-5,6-cyclohexylidenedioxy-3-methylhex-1-ene (1234580-28-9) → (2R,3S,4R)-3-tert-butyldiphenylsilyloxy-4,5-cyclohexylidenedioxy-2-methylpentanal (1315500-59-4)

Guidance literature:

(3S,4S,5R)-4-tert-butyldiphenylsilyloxy-5,6-cyclohexylidenedioxy-3-methylhex-1-ene; With ozone; In dichloromethane; at -78 ℃; for 1h;

With triphenylphosphine; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1055/s-0030-1260014

Reference yield:

(2R,3S,4S)-1,2-cyclohexylidenedioxy-4-methylhex-5-en-3-ol (181139-28-6) → (2R,3S,4R)-3-tert-butyldiphenylsilyloxy-4,5-cyclohexylidenedioxy-2-methylpentanal (1315500-59-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole / dichloromethane / 12 h / 25 °C

2.1: ozone / dichloromethane / 1 h / -78 °C

2.2: 16 h / 20 °C / Inert atmosphere

With 1H-imidazole; ozone; In dichloromethane;

DOI:10.1055/s-0030-1260014

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3S,4R)-3-tert-butyldiphenylsilyloxy-4,5-cyclohexylidenedioxy-2-methylpentanal (1315500-59-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole / dichloromethane / 12 h / 25 °C

2.1: ozone / dichloromethane / 1 h / -78 °C

2.2: 16 h / 20 °C / Inert atmosphere

With 1H-imidazole; ozone; In dichloromethane;

DOI:10.1055/s-0030-1260014

upstream raw materials:

(3S,4S,5R)-4-tert-butyldiphenylsilyloxy-5,6-cyclohexylidenedioxy-3-methylhex-1-ene

tert-butylchlorodiphenylsilane

(2R,3S,4S)-1,2-cyclohexylidenedioxy-4-methylhex-5-en-3-ol

Downstream raw materials:

(2S,3S)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]hex-5-en-3-ol

(4S,5S,6S,7R)-4-benzoyloxy-6-tert-butyldiphenylsilyloxy-7,8-cyclohexylidenedioxy-5-methyloct-1-ene

(2R,3S,4R,5S)-5-benzoyloxy-1,2-cyclohexylidenedioxy-4-methyloct-7-en-3-ol

(2R,3R,4R,5S)-5-benzoyloxy-1,2-cyclohexylidenedioxy-4-methyloct-7-en-3-ol