(S,E)-1-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-1-en-3-ol

Base Information

• Chemical Name: (S,E)-1-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-1-en-3-ol
• CAS No.: 864875-39-8
• Molecular Formula: C₂₇H₃₈O₄Si
• Molecular Weight: 454.682
• Mol file: 864875-39-8.mol

Synonyms:(S,E)-1-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-1-en-3-ol

Chemical Property of (S,E)-1-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-1-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-1-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-1-en-3-ol

There total 1 articles about (S,E)-1-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-1-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: 79.0%

(Z)-3-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylaldehyde + diethylzinc (557-20-0) → (E)-(R)-1-[(4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pent-1-en-3-ol + (S,E)-1-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-1-en-3-ol (864875-39-8)

Guidance literature:

With chiral Soai catalyst; In cyclohexane; at 0 - 20 ℃;

DOI:10.1002/anie.200500892

Reference yield: 93.0%

(S,E)-1-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-1-en-3-ol (864875-39-8) + Trichloroacetyl isocyanate (3019-71-4) → (E)-1-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-1-en-3-yl carbamate (864875-40-1)

Guidance literature:

(S,E)-1-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-1-en-3-ol; Trichloroacetyl isocyanate; In dichloromethane; at 20 ℃; for 1h;

With water; potassium carbonate; In methanol; dichloromethane; at 0 ℃;

DOI:10.1002/chem.200901745

Reference yield:

(S,E)-1-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-1-en-3-ol (864875-39-8) → tert-Butyl-[(4R,5R)-5-((E)-(S)-1-isocyanato-pent-2-enyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-diphenyl-silane (1054668-74-4)

Guidance literature:

Multi-step reaction with 3 steps

1: CH₂Cl₂

2: aq. K₂CO₃ / methanol

3: PPh₃; CBr₄; Et₃N / CH₂Cl₂ / -40 °C

With carbon tetrabromide; potassium carbonate; triethylamine; triphenylphosphine; In methanol; dichloromethane;

DOI:10.1002/anie.200500892

upstream raw materials:

diethylzinc

Downstream raw materials:

tert-Butyl-[(4R,5R)-5-((E)-(S)-1-isocyanato-pent-2-enyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-diphenyl-silane

(E)-1-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-1-en-3-yl carbamate

2,2,2-trichloroethyl (S,E)-1-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-2-enylcarbamate

(6R,7R,8S)-8-((E)-but-1-enyl)-13,13,13-trichloro-2,2-dimethyl-10-oxo-3,3-diphenyl-4,11-dioxa-9-aza-3-silatridecane-6,7-diyl diacetate