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

Base Information

• Chemical Name: (E)-1-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-1-en-3-yl carbamate
• CAS No.: 864875-40-1
• Molecular Formula: C₂₈H₃₉NO₅Si
• Molecular Weight: 497.707
• Mol file: 864875-40-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

(2,2,2-Trichloro-acetyl)-carbamic acid (E)-(S)-3-[(4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-ethyl-allyl ester → (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:

With potassium carbonate; In methanol;

DOI:10.1002/anie.200500892

Reference yield:

(Z)-3-((4R,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylaldehyde → (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:

Multi-step reaction with 3 steps

1: 79 percent / chiral Soai catalyst / cyclohexane / 0 - 20 °C

2: CH₂Cl₂

3: aq. K₂CO₃ / methanol

With chiral Soai catalyst; potassium carbonate; In methanol; dichloromethane; cyclohexane;

DOI:10.1002/anie.200500892

upstream raw materials:

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

Trichloroacetyl isocyanate

Downstream raw materials:

(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

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

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