(R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4S,6R)-4-(4-methoxy-benzyloxy)-5,5-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl]-N-phenyl-butyramide

Base Information

• Chemical Name: (R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4S,6R)-4-(4-methoxy-benzyloxy)-5,5-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl]-N-phenyl-butyramide
• CAS No.: 247146-43-6
• Molecular Formula: C₃₇H₅₁NO₅SSi
• Molecular Weight: 649.967
• Mol file: 247146-43-6.mol

Synonyms:(R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4S,6R)-4-(4-methoxy-benzyloxy)-5,5-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl]-N-phenyl-butyramide

Chemical Property of (R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4S,6R)-4-(4-methoxy-benzyloxy)-5,5-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl]-N-phenyl-butyramide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4S,6R)-4-(4-methoxy-benzyloxy)-5,5-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl]-N-phenyl-butyramide

There total 15 articles about (R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4S,6R)-4-(4-methoxy-benzyloxy)-5,5-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl]-N-phenyl-butyramide 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: 86.0%

phenylthiotrimethylsilane (4551-15-9) + Acetic acid (4S,6S)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-phenylcarbamoyl-propyl]-4-(4-methoxy-benzyloxy)-3,3-dimethyl-tetrahydro-pyran-2-yl ester → (R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4S,6R)-4-(4-methoxy-benzyloxy)-5,5-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl]-N-phenyl-butyramide (247146-43-6) + (R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4S,6S)-4-(4-methoxy-benzyloxy)-5,5-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl]-N-phenyl-butyramide

Guidance literature:

With tetra-(n-butyl)ammonium iodide; zinc(II) iodide; In dichloromethane;

DOI:10.1021/ja990860j

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4S,6R)-4-(4-methoxy-benzyloxy)-5,5-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl]-N-phenyl-butyramide (247146-43-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 64 percent / 2,6-lutidine / CH₂Cl₂ / -10 °C

2.1: Me₃Al / CH₂Cl₂ / 30 °C

2.2: 75 percent / CH₂Cl₂ / 0 °C

3.1: O₃ / CH₂Cl₂; methanol / -78 °C

3.2: 72 percent / Me₂S / CH₂Cl₂; methanol

4.1: pyridine / 48 h / 23 °C

5.1: 86 percent / ZnI₂; n-Bu₄NI / CH₂Cl₂

With pyridine; 2,6-dimethylpyridine; trimethylaluminum; tetra-(n-butyl)ammonium iodide; ozone; zinc(II) iodide; In methanol; dichloromethane; 1.1: silylation / 2.1: trimethylalumination / 2.2: Ring cleavage / 3.1: ozonolysis / 3.2: Reduction / 4.1: Acetylation / 5.1: Substitution;

DOI:10.1021/ja990860j

Reference yield:

(4R,6R)-4-Hydroxy-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one (247146-39-0) → (R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4S,6R)-4-(4-methoxy-benzyloxy)-5,5-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl]-N-phenyl-butyramide (247146-43-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 64 percent / 2,6-lutidine / CH₂Cl₂ / -10 °C

2.1: Me₃Al / CH₂Cl₂ / 30 °C

2.2: 75 percent / CH₂Cl₂ / 0 °C

3.1: O₃ / CH₂Cl₂; methanol / -78 °C

3.2: 72 percent / Me₂S / CH₂Cl₂; methanol

4.1: pyridine / 48 h / 23 °C

5.1: 86 percent / ZnI₂; n-Bu₄NI / CH₂Cl₂

With pyridine; 2,6-dimethylpyridine; trimethylaluminum; tetra-(n-butyl)ammonium iodide; ozone; zinc(II) iodide; In methanol; dichloromethane; 1.1: silylation / 2.1: trimethylalumination / 2.2: Ring cleavage / 3.1: ozonolysis / 3.2: Reduction / 4.1: Acetylation / 5.1: Substitution;

DOI:10.1021/ja990860j

upstream raw materials:

phenylthiotrimethylsilane

t-butyldimethylsiyl triflate

(S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-enal

(4R,6R)-4-Hydroxy-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one

Downstream raw materials:

(R)-4-[(2S,4S,6R)-6-Benzenesulfonyl-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-N-phenyl-butyramide

C₇₁H₁₁₅NO₁₂Si₃

C₇₇H₁₂₉NO₁₂Si₄