(4S,5R,E)-ethyl 5-azido-6-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)hex-2-enoate

Base Information

• Chemical Name: (4S,5R,E)-ethyl 5-azido-6-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)hex-2-enoate
• CAS No.: 1609543-99-8
• Molecular Formula: C₂₁H₃₃N₃O₄Si
• Molecular Weight: 419.596
• Mol file: 1609543-99-8.mol

Synonyms:(4S,5R,E)-ethyl 5-azido-6-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)hex-2-enoate

Chemical Property of (4S,5R,E)-ethyl 5-azido-6-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)hex-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,E)-ethyl 5-azido-6-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)hex-2-enoate

There total 1 articles about (4S,5R,E)-ethyl 5-azido-6-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)hex-2-enoate 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%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (2R,3R)-3-azido-4-(benzyloxy)-2-(tert-butyldimethylsilyloxy)butanal (1380426-13-0) → (4S,5R,E)-ethyl 5-azido-6-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)hex-2-enoate (1609543-99-8)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at 0 ℃;

(2R,3R)-3-azido-4-(benzyloxy)-2-(tert-butyldimethylsilyloxy)butanal; In tetrahydrofuran; at 25 ℃; for 1h;

DOI:10.1055/s-0033-1340074

Reference yield:

(4S,5R,E)-ethyl 5-azido-6-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)hex-2-enoate (1609543-99-8) → (2R,3S)-tert-butyl 2-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)piperidine-1-carboxylate (1174386-88-9)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 25 °C / 760.05 Torr

2: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 °C / Reflux; Inert atmosphere

3: sodium carbonate / water; dichloromethane / 12 h / 25 °C

With dimethylsulfide borane complex; palladium 10% on activated carbon; hydrogen; sodium carbonate; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1055/s-0033-1340074

Reference yield:

(4S,5R,E)-ethyl 5-azido-6-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)hex-2-enoate (1609543-99-8) → C19H33NO2Si (1609544-00-4)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 25 °C / 760.05 Torr

2: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 °C / Reflux; Inert atmosphere

With dimethylsulfide borane complex; palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol;

DOI:10.1055/s-0033-1340074

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

(2R,3R)-3-azido-4-(benzyloxy)-2-(tert-butyldimethylsilyloxy)butanal

Downstream raw materials:

(2R,3S)-tert-butyl 2-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)piperidine-1-carboxylate

(2R,3S)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)piperidine-1-carboxylate

C₁₉H₃₃NO₂Si