(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

Base Information

• Chemical Name: (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
• CAS No.: 192371-15-6
• Molecular Formula: C₃₇H₅₁NO₇SSi
• Molecular Weight: 681.966
• Mol file: 192371-15-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 16 articles about (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 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: 76.0%

(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) → (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 (192371-15-6)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In ethyl acetate;

DOI:10.1021/ja990860j

Reference yield:

phenylthiotrimethylsilane (4551-15-9) → (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 (192371-15-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / ZnI₂; n-Bu₄NI / CH₂Cl₂

2: 76 percent / m-CPBA; NaHCO₃ / ethyl acetate

With tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; zinc(II) iodide; In dichloromethane; ethyl acetate; 1: Substitution / 2: Oxidation;

DOI:10.1021/ja990860j

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (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 (192371-15-6)

Guidance literature:

Multi-step reaction with 6 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

6.1: 76 percent / m-CPBA; NaHCO₃ / ethyl acetate

With pyridine; 2,6-dimethylpyridine; trimethylaluminum; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; ozone; 3-chloro-benzenecarboperoxoic acid; zinc(II) iodide; In methanol; dichloromethane; ethyl acetate; 1.1: silylation / 2.1: trimethylalumination / 2.2: Ring cleavage / 3.1: ozonolysis / 3.2: Reduction / 4.1: Acetylation / 5.1: Substitution / 6.1: Oxidation;

DOI:10.1021/ja990860j

upstream raw materials:

(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

phenylthiotrimethylsilane

t-butyldimethylsiyl triflate

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

Downstream raw materials:

C₇₇H₁₂₉NO₁₂Si₄

C₇₁H₁₁₅NO₁₂Si₃