(2S,3R,4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2,4-dimethyl-heptan-1-one

Base Information

• Chemical Name: (2S,3R,4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2,4-dimethyl-heptan-1-one
• CAS No.: 899798-74-4
• Molecular Formula: C₃₂H₅₃NO₆SSi
• Molecular Weight: 607.927
• Mol file: 899798-74-4.mol

Synonyms:(2S,3R,4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2,4-dimethyl-heptan-1-one

Chemical Property of (2S,3R,4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2,4-dimethyl-heptan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2,4-dimethyl-heptan-1-one

There total 5 articles about (2S,3R,4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2,4-dimethyl-heptan-1-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:

(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal (872369-17-0) + (2S)-N-propionylcamphorsultam (128947-19-3) → (2S,3R,4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-hydroxy-2,4-dimethyl-heptan-1-one (899798-74-4)

Guidance literature:

(2S)-N-propionylcamphorsultam; With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -5 ℃; for 0.5h;

(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal; In dichloromethane; at -78 ℃; for 16h;

DOI:10.1021/ol060669w

Reference yield:

(2R,3S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-methyl-pentan-1-one (899798-73-3) → (2S,3R,4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-hydroxy-2,4-dimethyl-heptan-1-one (899798-74-4)

Guidance literature:

Multi-step reaction with 2 steps

1: diisoibutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

2: CH₂Cl₂ / 16 h / -78 °C

With diisoibutylaluminum hydride; In hexane; dichloromethane; 2: Evans asymmetric aldolization;

DOI:10.1002/chem.200700342

Reference yield:

3-Benzyloxypropanal (19790-60-4) → (2S,3R,4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-hydroxy-2,4-dimethyl-heptan-1-one (899798-74-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: nBu₂BOTf; N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / -5 °C

1.2: 95 percent / CH₂Cl₂ / 16 h / -78 °C

2.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

3.1: diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

4.1: nBu₂BOTf; N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / -5 °C

4.2: 3.98 g / CH₂Cl₂ / 16 h / -78 °C

With 2,6-dimethylpyridine; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane;

DOI:10.1021/ol060669w

upstream raw materials:

(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal

(2S)-N-propionylcamphorsultam

(2R,3S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methyl-pentan-1-one

3-Benzyloxypropanal

Downstream raw materials:

(3S,4R,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-one

(2S,3R,4R,5S)-7-Benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoic acid

[(3S,4R,5S,6R,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-octyloxymethyl]-benzene

(2S,3R,4R,5S)-7-Benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoic acid methoxy-methyl-amide