(S)-2-(N,N'-dibenzyloxycarbonylhydrazino)-5-bromo-1-(tert-butyldimethylsiloxy)pentane

Base Information

• Chemical Name: (S)-2-(N,N'-dibenzyloxycarbonylhydrazino)-5-bromo-1-(tert-butyldimethylsiloxy)pentane
• CAS No.: 816454-06-5
• Molecular Formula: C₂₇H₃₉BrN₂O₅Si
• Molecular Weight: 579.607
• Mol file: 816454-06-5.mol

Synonyms:(S)-2-(N,N'-dibenzyloxycarbonylhydrazino)-5-bromo-1-(tert-butyldimethylsiloxy)pentane

Chemical Property of (S)-2-(N,N'-dibenzyloxycarbonylhydrazino)-5-bromo-1-(tert-butyldimethylsiloxy)pentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2-(N,N'-dibenzyloxycarbonylhydrazino)-5-bromo-1-(tert-butyldimethylsiloxy)pentane

There total 3 articles about (S)-2-(N,N'-dibenzyloxycarbonylhydrazino)-5-bromo-1-(tert-butyldimethylsiloxy)pentane 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: 82.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (S)-5-bromo-2-N,N'-dibenzyloxycarbonylhydrazino-1-pentanol (816454-01-0) → (S)-2-(N,N'-dibenzyloxycarbonylhydrazino)-5-bromo-1-(tert-butyldimethylsiloxy)pentane (816454-06-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 23 ℃; for 3.5h;

DOI:10.1016/j.tetasy.2004.09.025

Reference yield:

5-bromopentanal (1191-30-6) → (S)-2-(N,N'-dibenzyloxycarbonylhydrazino)-5-bromo-1-(tert-butyldimethylsiloxy)pentane (816454-06-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (R)-proline / acetonitrile / 15 h / 0 °C

1.2: 100 percent / NaBH₄ / acetonitrile; ethanol / 0.67 h / 0 °C

2.1: 82 percent / imidazole / dimethylformamide / 3.5 h / 23 °C

With 1H-imidazole; D-Prolin; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tetasy.2004.09.025

Reference yield:

dibenzyl azodicarboxylate (2449-05-0) → (S)-2-(N,N'-dibenzyloxycarbonylhydrazino)-5-bromo-1-(tert-butyldimethylsiloxy)pentane (816454-06-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (R)-proline / acetonitrile / 15 h / 0 °C

1.2: 100 percent / NaBH₄ / acetonitrile; ethanol / 0.67 h / 0 °C

2.1: 82 percent / imidazole / dimethylformamide / 3.5 h / 23 °C

With 1H-imidazole; D-Prolin; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tetasy.2004.09.025

upstream raw materials:

tert-butyldimethylsilyl chloride

(S)-5-bromo-2-N,N'-dibenzyloxycarbonylhydrazino-1-pentanol

5-bromopentanal

dibenzyl azodicarboxylate

Downstream raw materials:

(S)-1,2-di(benzyloxycarbonyl)hexahydropyridazine-3-carboxylic acid

(S)-1,2-dibenzyloxycarbonyl-3-hydroxymethyl-tetrahydropyridazine

(S)-1,2-dibenzyloxycarbonyl-3-(tert-butyldimethylsiloxymethyl)tetrahydropyridazine