(2R,3S)-5-(tert-Butyl-diphenyl-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)-3-methoxymethoxy-2-methyl-pentan-1-one

Base Information

• Chemical Name: (2R,3S)-5-(tert-Butyl-diphenyl-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)-3-methoxymethoxy-2-methyl-pentan-1-one
• CAS No.: 899798-68-6
• Molecular Formula: C₃₄H₄₉NO₆SSi
• Molecular Weight: 627.918

Synonyms:(2R,3S)-5-(tert-Butyl-diphenyl-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)-3-methoxymethoxy-2-methyl-pentan-1-one

Chemical Property of (2R,3S)-5-(tert-Butyl-diphenyl-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)-3-methoxymethoxy-2-methyl-pentan-1-one

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Technology Process of (2R,3S)-5-(tert-Butyl-diphenyl-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)-3-methoxymethoxy-2-methyl-pentan-1-one

There total 3 articles about (2R,3S)-5-(tert-Butyl-diphenyl-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)-3-methoxymethoxy-2-methyl-pentan-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:

N-propionyl-(2R)-bornane-(10,2)-sultam (125664-95-1) → (2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-methoxymethoxy-2-methyl-pentan-1-one (899798-68-6)

Guidance literature:

Multi-step reaction with 3 steps

1: iPr₂NEt / CH₂Cl₂ / 0.5 h / -5 °C

2: CH₂Cl₂ / 16 h / -78 °C

3: 91 percent / iPr₂NEt / CH₂Cl₂ / 4 h / Heating

With N-ethyl-N,N-diisopropylamine; In dichloromethane; 2: Evans asymmetric aldolization;

DOI:10.1002/chem.200700342

Reference yield:

3-(tert-butyldiphenylsilyloxy)-1-propanal (112897-03-7) → (2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-methoxymethoxy-2-methyl-pentan-1-one (899798-68-6)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 94 percent / CH₂Cl₂ / 16 h / -78 °C

2.1: 91 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 4 h / Heating

With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/ol060669w

Reference yield:

C21H38NBSO3 → (2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-methoxymethoxy-2-methyl-pentan-1-one (899798-68-6)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 16 h / -78 °C

2: 91 percent / iPr₂NEt / CH₂Cl₂ / 4 h / Heating

With N-ethyl-N,N-diisopropylamine; In dichloromethane; 1: Evans asymmetric aldolization;

DOI:10.1002/chem.200700342

upstream raw materials:

N-propionyl-(2R)-bornane-(10,2)-sultam

3-(tert-butyldiphenylsilyloxy)-1-propanal

Downstream raw materials:

(2S,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-2-methyl-pentan-1-ol

5-[(E)-(3S,4S,9S,10R,11S,12R,13S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-13-methoxy-3-methoxymethoxy-4,10,12-trimethyl-tetradec-6-ene-1-sulfonyl]-1-phenyl-1H-tetrazole

C₄₈H₈₆O₆Si₃

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