tert-butyl (S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-enyl carbamate

Base Information

• Chemical Name: tert-butyl (S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-enyl carbamate
• CAS No.: 921201-39-0
• Molecular Formula: C₂₃H₃₃NO₇
• Molecular Weight: 435.518
• Mol file: 921201-39-0.mol

Synonyms:tert-butyl (S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-enyl carbamate

Chemical Property of tert-butyl (S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-enyl carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-enyl carbamate

There total 1 articles about tert-butyl (S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-enyl 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:

tert-butoxycarbonylamino-(ethoxy-ethoxymethyl-phosphinoyl)-acetic acid ethyl ester + 2-O-benzyl-3,4-O-isopropylidene-L-threose (100906-42-1) → tert-butyl (S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-enyl carbamate (921201-39-0)

Guidance literature:

tert-butoxycarbonylamino-(ethoxy-ethoxymethyl-phosphinoyl)-acetic acid ethyl ester; With potassium tert-butylate; In dichloromethane; for 0.5h; cooling;

2-O-benzyl-3,4-O-isopropylidene-L-threose; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1016/j.tetasy.2006.10.033

Reference yield: 74.0%

tert-butyl (S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-enyl carbamate (921201-39-0) → tert-butyl-(1S,3S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl carbamate (921201-40-3) + tert-butyl-(1R,3S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl carbamate (921201-50-5)

Guidance literature:

With hydrogen; sodium carbonate; palladium on activated charcoal; In ethyl acetate; for 3h; atmospheric pressure;

DOI:10.1016/j.tetasy.2006.10.033

Reference yield:

tert-butyl (S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-enyl carbamate (921201-39-0) → (2R,4S,5R)-ethyl-4-(benzyloxy)-5-(tert-butyl dimethyl silyloxy methyl)pyrrolidine-2-carboxylate (921201-54-9)

Guidance literature:

Multi-step reaction with 5 steps

1: Na₂CO₃; hydrogen / palladium on carbon / ethyl acetate / 3 h / atmospheric pressure

2: pyridinium para-toluenesulfonate / ethanol / Heating

3: imidazole / CH₂Cl₂ / 20 °C

4: DIPEA; methanesulfonyl chloride / CH₂Cl₂ / 20 °C

5: trifluoroacetic acid / CH₂Cl₂ / 20 °C

With 1H-imidazole; hydrogen; pyridinium p-toluenesulfonate; sodium carbonate; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate;

DOI:10.1016/j.tetasy.2006.10.033

upstream raw materials:

2-O-benzyl-3,4-O-isopropylidene-L-threose

Downstream raw materials:

tert-butyl-(1S,3S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl carbamate

tert-butyl-(1R,3S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl carbamate

(2S,4S,5R)-ethyl-4-(benzyloxy)-5-(tert-butyl dimethyl silyloxy methyl)pyrrolidine-2-carboxylate

(2R,4S,5R)-ethyl-4-(benzyloxy)-5-(tert-butyl dimethyl silyloxy methyl)pyrrolidine-2-carboxylate