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

Base Information

• Chemical Name: (2S,3S)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]hex-5-en-3-ol
• CAS No.: 932739-33-8
• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.376
• Mol file: 932739-33-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 28 articles about (2S,3S)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]hex-5-en-3-ol 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: 77.0%

(R)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]propanal (932739-32-7) + allyltributylstanane (24850-33-7) → (2S,3S)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]hex-5-en-3-ol (932739-33-8)

Guidance literature:

(R)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]propanal; With magnesium bromide; In dichloromethane; at -78 ℃; for 0.25h;

allyltributylstanane; In dichloromethane; at -78 ℃; for 12h;

DOI:10.1021/ol063032l

Reference yield: 72.0%

(4S,5S,6R,7R)-4-benzoyloxy-6,7-isopropylidenedioxy-5-methyl-7-phenylhept-1-ene (1315500-68-5) → (2S,3S)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]hex-5-en-3-ol (932739-33-8)

Guidance literature:

With water; potassium carbonate; In methanol; at 20 ℃; for 3h;

DOI:10.1055/s-0030-1260014

Reference yield:

methyl (R)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]propanoate (932739-31-6) → (2S,3S)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]hex-5-en-3-ol (932739-33-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 100 percent / DIBAL-H / CH₂Cl₂; toluene / 4 h / -78 °C

2.1: MgBr₂*Et₂O / CH₂Cl₂ / 0.25 h / -78 °C

2.2: 77 percent / CH₂Cl₂ / 12 h / -78 °C

With diisobutylaluminium hydride; magnesium bromide; In dichloromethane; toluene;

DOI:10.1021/ol063032l

upstream raw materials:

(R)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]propanal

allyltributylstanane

methyl (R)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]propanoate

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

Downstream raw materials:

C₃₇H₄₈N₂O₉

C₃₄H₄₄N₂O₉

cryptophycin-24

C₃₉H₅₂N₂O₉