4-Benzyl-3-[(2S,3R,5R,6S)-2-(3-benzyloxy-propyl)-7-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-methoxy-6-methyl-heptanoyl]-oxazolidin-2-one

Base Information

• Chemical Name: 4-Benzyl-3-[(2S,3R,5R,6S)-2-(3-benzyloxy-propyl)-7-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-methoxy-6-methyl-heptanoyl]-oxazolidin-2-one
• CAS No.: 142945-20-8
• Molecular Formula: C₄₅H₅₇NO₇Si
• Molecular Weight: 752.036
• Mol file: 142945-20-8.mol

Synonyms:

Chemical Property of 4-Benzyl-3-[(2S,3R,5R,6S)-2-(3-benzyloxy-propyl)-7-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-methoxy-6-methyl-heptanoyl]-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Benzyl-3-[(2S,3R,5R,6S)-2-(3-benzyloxy-propyl)-7-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-methoxy-6-methyl-heptanoyl]-oxazolidin-2-one

There total 7 articles about 4-Benzyl-3-[(2S,3R,5R,6S)-2-(3-benzyloxy-propyl)-7-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-methoxy-6-methyl-heptanoyl]-oxazolidin-2-one 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: 58.0%

5-(tert-Butyldiphenylsilanyloxy)-3-methoxy-4-methylpentanal (142954-43-6) + 4-Benzyl-3-(5-benzyloxy-pentanoyl)-oxazolidin-2-one (142945-19-5) → 4-Benzyl-3-[(2S,3R,5R,6S)-2-(3-benzyloxy-propyl)-7-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-methoxy-6-methyl-heptanoyl]-oxazolidin-2-one (142945-20-8)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; triethylamine;

DOI:10.1016/S0040-4039(00)79858-3

Reference yield:

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol (89956-14-9) → 4-Benzyl-3-[(2S,3R,5R,6S)-2-(3-benzyloxy-propyl)-7-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-methoxy-6-methyl-heptanoyl]-oxazolidin-2-one (142945-20-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 60 percent / CuI

2: 84 percent

3: 84 percent / NaH

4: 100 percent / H₂ / Pd(OH)2-C

5: 94 percent / (COCl)2, DMSO, Et₃N

6: 58 percent / Bu₂BOTf, Et₃N

With oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; copper(l) iodide; palladium hydroxide - carbon;

DOI:10.1016/S0040-4039(00)79858-3

Reference yield:

(E)-5-(benzyloxy)pent-2-en-1-ol (89923-31-9) → 4-Benzyl-3-[(2S,3R,5R,6S)-2-(3-benzyloxy-propyl)-7-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-methoxy-6-methyl-heptanoyl]-oxazolidin-2-one (142945-20-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 72 percent / (-)-DET, Ti(OⁱPr)4, ^tBuOOH

2: 60 percent / CuI

3: 84 percent

4: 84 percent / NaH

5: 100 percent / H₂ / Pd(OH)2-C

6: 94 percent / (COCl)2, DMSO, Et₃N

7: 58 percent / Bu₂BOTf, Et₃N

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; sodium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; copper(l) iodide; palladium hydroxide - carbon;

DOI:10.1016/S0040-4039(00)79858-3

upstream raw materials:

5-(tert-Butyldiphenylsilanyloxy)-3-methoxy-4-methylpentanal

4-Benzyl-3-(5-benzyloxy-pentanoyl)-oxazolidin-2-one

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol

(E)-5-(benzyloxy)pent-2-en-1-ol

Downstream raw materials:

(2R,3R,5R,6S)-2-(3-Benzyloxy-propyl)-7-(tert-butyl-diphenyl-silanyloxy)-5-methoxy-3-methoxymethoxy-6-methyl-heptan-1-ol

(E)-(4R,5R,9S,10R,12R,13S)-16-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4,10-dimethoxy-12-methoxymethoxy-5,9,13-trimethyl-hexadec-7-en-6-one

(2R,3R,5R,6S)-9-Benzyloxy-3-methoxy-5-methoxymethoxy-2,6-dimethyl-nonanal

(2S,3R,5R,6S)-9-Benzyloxy-3-methoxy-5-methoxymethoxy-2,6-dimethyl-nonan-1-ol