tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldimethyldimethylsilyloxy)pentan-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldimethyldimethylsilyloxy)pentan-2-ylcarbamate
• CAS No.: 1618679-31-4
• Molecular Formula: C₂₃H₄₁NO₄Si
• Molecular Weight: 423.668
• Mol file: 1618679-31-4.mol

Synonyms:tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldimethyldimethylsilyloxy)pentan-2-ylcarbamate

Chemical Property of tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldimethyldimethylsilyloxy)pentan-2-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldimethyldimethylsilyloxy)pentan-2-ylcarbamate

There total 1 articles about tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldimethyldimethylsilyloxy)pentan-2-ylcarbamate 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: 85.0%

C16H35NO4Si + benzyl bromide (100-39-0) → tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldimethyldimethylsilyloxy)pentan-2-ylcarbamate (1618679-31-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 12h;

DOI:10.1080/00397911.2014.899605

Reference yield: 92.0%

tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldimethyldimethylsilyloxy)pentan-2-ylcarbamate (1618679-31-4) → tert-butyl (2S,3R)-3-(benzyloxy)-1-hydroxypentan-2-ylcarbamate (1175524-30-7)

Guidance literature:

With tetrabutyl ammonium fluoride; at 20 ℃; for 1h;

DOI:10.1080/00397911.2014.899605

Reference yield:

tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldimethyldimethylsilyloxy)pentan-2-ylcarbamate (1618679-31-4) → C17H25NO4

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / 1 h / 20 °C

2: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

With tetrabutyl ammonium fluoride; Dess-Martin periodane; In dichloromethane; 2: |Dess-Martin Oxidation;

DOI:10.1080/00397911.2014.899605

upstream raw materials:

benzyl bromide

Downstream raw materials:

tert-butyl (2S,3R)-3-(benzyloxy)-1-hydroxypentan-2-ylcarbamate

tert-butyl (3R,4S,E)-3,8-bis(benzyloxy)oct-5-en-4-ylcarbamate

(4S,5R,E)-ethyl 5-(benzyloxy)-4-(tert-butoxycarbonylamino)hept-2-enoate

C₂₁H₃₃NO₅