(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-hydroxy-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-hydroxy-2-methyl-pentan-1-one
• CAS No.: 899798-67-5
• Molecular Formula: C₃₂H₄₅NO₅SSi
• Molecular Weight: 583.865

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-hydroxy-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-hydroxy-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-hydroxy-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-hydroxy-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: 94.0%

N-propionyl-(2R)-bornane-(10,2)-sultam (125664-95-1) + 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-hydroxy-2-methyl-pentan-1-one (899798-67-5)

Guidance literature:

N-propionyl-(2R)-bornane-(10,2)-sultam; With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -5 ℃; for 0.5h;

3-(tert-butyldiphenylsilyloxy)-1-propanal; In dichloromethane; at -78 ℃; for 16h;

DOI:10.1021/ol060669w

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-hydroxy-2-methyl-pentan-1-one (899798-67-5)

Guidance literature:

Multi-step reaction with 2 steps

1: iPr₂NEt / CH₂Cl₂ / 0.5 h / -5 °C

2: CH₂Cl₂ / 16 h / -78 °C

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

DOI:10.1002/chem.200700342

Reference yield:

C21H38NBSO3 + 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-hydroxy-2-methyl-pentan-1-one (899798-67-5)

Guidance literature:

In dichloromethane; at -78 ℃; for 16h;

DOI:10.1002/chem.200700342

upstream raw materials:

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

3-(tert-butyldiphenylsilyloxy)-1-propanal

Downstream raw materials:

C₄₈H₈₆O₆Si₃

(3S,4S)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3-methyl-hexanenitrile

(3S,4S)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3-methyl-hexanal

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

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