(2R,3S)-3-O-(t-butyldimethylsilyl)-1-O-(t-butyldiphenylsilyl)-2-{[(t-butyloxy)carbonyl]amino}-4-pentene-1,3-diol

Base Information

• Chemical Name: (2R,3S)-3-O-(t-butyldimethylsilyl)-1-O-(t-butyldiphenylsilyl)-2-{[(t-butyloxy)carbonyl]amino}-4-pentene-1,3-diol
• CAS No.: 852068-34-9
• Molecular Formula: C₃₂H₅₁NO₄Si₂
• Molecular Weight: 569.932
• Mol file: 852068-34-9.mol

Synonyms:(2R,3S)-3-O-(t-butyldimethylsilyl)-1-O-(t-butyldiphenylsilyl)-2-{[(t-butyloxy)carbonyl]amino}-4-pentene-1,3-diol

Chemical Property of (2R,3S)-3-O-(t-butyldimethylsilyl)-1-O-(t-butyldiphenylsilyl)-2-{[(t-butyloxy)carbonyl]amino}-4-pentene-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-O-(t-butyldimethylsilyl)-1-O-(t-butyldiphenylsilyl)-2-{[(t-butyloxy)carbonyl]amino}-4-pentene-1,3-diol

There total 1 articles about (2R,3S)-3-O-(t-butyldimethylsilyl)-1-O-(t-butyldiphenylsilyl)-2-{[(t-butyloxy)carbonyl]amino}-4-pentene-1,3-diol 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: 91.0%

(2R,3S)-1-O-(t-butyldiphenylsilyl)-2-{[(t-butyloxy)carbonyl]amino}-4-pentene-1,3-diol (852068-33-8) + tert-butyldimethylsilyl chloride (18162-48-6) → (2R,3S)-3-O-(t-butyldimethylsilyl)-1-O-(t-butyldiphenylsilyl)-2-{[(t-butyloxy)carbonyl]amino}-4-pentene-1,3-diol (852068-34-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1002/anie.200462439 DOI:10.1021/jo701699h

Reference yield:

(2R,3S)-3-O-(t-butyldimethylsilyl)-1-O-(t-butyldiphenylsilyl)-2-{[(t-butyloxy)carbonyl]amino}-4-pentene-1,3-diol (852068-34-9) + methyl iodide (74-88-4) → [2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl]-methyl-carbamic acid tert-butyl ester

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 10h;

DOI:10.1002/anie.200462439

Reference yield:

(2R,3S)-3-O-(t-butyldimethylsilyl)-1-O-(t-butyldiphenylsilyl)-2-{[(t-butyloxy)carbonyl]amino}-4-pentene-1,3-diol (852068-34-9) → (2R,3S)-3-O-(t-butyldimethylsilyl)-1-O-(t-butyldiphenylsilyl)-2-(methylamino)-4-pentene-1,3-diol (852068-20-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 10 h / 20 °C

2.1: HCl / ethyl acetate / 0.08 h / 0 °C

2.2: 361 mg / imidazole / dimethylformamide / 12 h / 20 °C

With hydrogenchloride; sodium hydride; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/anie.200462439

upstream raw materials:

(2R,3S)-1-O-(t-butyldiphenylsilyl)-2-{[(t-butyloxy)carbonyl]amino}-4-pentene-1,3-diol

tert-butyldimethylsilyl chloride

Downstream raw materials:

(2R,3S)-3-O-(t-butyldimethylsilyl)-1-O-(t-butyldiphenylsilyl)-2-(methylamino)-4-pentene-1,3-diol