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

Base Information

• Chemical Name: tert-butyl-(1R,3S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl carbamate
• CAS No.: 921201-50-5
• Molecular Formula: C₂₃H₃₅NO₇
• Molecular Weight: 437.533
• Mol file: 921201-50-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about tert-butyl-(1R,3S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl 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: 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-butoxycarbonylamino-(ethoxy-ethoxymethyl-phosphinoyl)-acetic acid ethyl ester → 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:

Multi-step reaction with 2 steps

1.1: potassium tert-butoxide / CH₂Cl₂ / 0.5 h / cooling

1.2: CH₂Cl₂ / 5 h / 20 °C

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

With potassium tert-butylate; hydrogen; sodium carbonate; palladium on activated charcoal; In dichloromethane; ethyl acetate; 1.2: Wittig-Horner reaction;

DOI:10.1016/j.tetasy.2006.10.033

Reference yield:

2-O-benzyl-3,4-O-isopropylidene-L-threose (100906-42-1) → 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:

Multi-step reaction with 2 steps

1.1: potassium tert-butoxide / CH₂Cl₂ / 0.5 h / cooling

1.2: CH₂Cl₂ / 5 h / 20 °C

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

With potassium tert-butylate; hydrogen; sodium carbonate; palladium on activated charcoal; In dichloromethane; ethyl acetate; 1.2: Wittig-Horner reaction;

DOI:10.1016/j.tetasy.2006.10.033

upstream raw materials:

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

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

Downstream raw materials:

tert-butyl-(1R,3S,4S)-1-(ethoxycarbonyl)-3-(benzyloxy)-4-hydroxy-5-(tert-butyl dimethyl silyloxy)-pentyl carbamate

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

tert-butyl-(1R,3S,4S)-1-(ethoxycarbonyl)-3-(benzyloxy)-4,5-dihydroxy pentyl carbamate