6-Oxabicyclo[3.2.1]oct-2-en-7-one, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[(2-nitrophenyl)methoxy]-, (1R,4R,5R)-

Base Information

• Chemical Name: 6-Oxabicyclo[3.2.1]oct-2-en-7-one, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[(2-nitrophenyl)methoxy]-, (1R,4R,5R)-
• CAS No.: 639806-91-0
• Molecular Formula: C20H27NO6Si
• Molecular Weight: 405.523
• Mol file: 639806-91-0.mol

Synonyms:

Chemical Property of 6-Oxabicyclo[3.2.1]oct-2-en-7-one, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[(2-nitrophenyl)methoxy]-, (1R,4R,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-Oxabicyclo[3.2.1]oct-2-en-7-one, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[(2-nitrophenyl)methoxy]-, (1R,4R,5R)-

There total 1 articles about 6-Oxabicyclo[3.2.1]oct-2-en-7-one, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[(2-nitrophenyl)methoxy]-, (1R,4R,5R)- 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: 54.0%

2-nitrophenylmethyl bromide (3958-60-9) + (1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-4-hydroxycyclohex-5-ene-1,3-carbolactone (356760-74-2) → (1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-4-(2'-nitrobenzyloxy)cyclohex-5-en-1,3-carbolactone (639806-91-0)

Guidance literature:

(1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-4-hydroxycyclohex-5-ene-1,3-carbolactone; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

2-nitrophenylmethyl bromide; With 15-crown-5; tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; at 80 ℃; for 24h;

DOI:10.1021/jm030987q

Reference yield: 71.0%

(1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-4-(2'-nitrobenzyloxy)cyclohex-5-en-1,3-carbolactone (639806-91-0) → (1R,3R,4R)-1-hydroxy-4-(2'-nitrobenzyloxy)cyclohex-5-en-1,3-carbolactone (639806-93-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jm030987q

Reference yield:

(1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-4-(2'-nitrobenzyloxy)cyclohex-5-en-1,3-carbolactone (639806-91-0) → (1R,4R,5R)-1,5-Dihydroxy-4-(2-nitro-benzyloxy)-cyclohex-2-enecarboxylic acid

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

2: 94 percent / aq. lithium hydroxide / tetrahydrofuran / 1 h / 20 °C

With lithium hydroxide; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/jm030987q

upstream raw materials:

2-nitrophenylmethyl bromide

(1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-4-hydroxycyclohex-5-ene-1,3-carbolactone

Downstream raw materials:

(1R,3R,4R)-1-hydroxy-4-(2'-nitrobenzyloxy)cyclohex-5-en-1,3-carbolactone