[(2S,5R,6S)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetaldehyde

Base Information

• Chemical Name: [(2S,5R,6S)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetaldehyde
• CAS No.: 249928-50-5
• Molecular Formula: C₃₈H₄₅NO₅SSi
• Molecular Weight: 655.93
• Mol file: 249928-50-5.mol

Synonyms:

Chemical Property of [(2S,5R,6S)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,5R,6S)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetaldehyde

There total 9 articles about [(2S,5R,6S)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetaldehyde 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:

(S)-1-(furan-2-yl)-2-tert-butyldiphenylsilyloxy-N-(toluene-4-sulfonyl)ethylamine (249928-44-7) → [(2S,5R,6S)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetaldehyde (249928-50-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 91 percent / m-CPBA / CH₂Cl₂

2: 95 percent / BF₃*OEt₂; 4 Angstroem mol. sieves / tetrahydrofuran / 0 °C

3: 91 percent / H₂ / Pd-C / ethyl acetate

4: 85 percent / NaBH₃CN / acetic acid; methanol / 0 - 20 °C

5: 91 percent / NaH; Bu₄NI / tetrahydrofuran

6: 87 percent / TiCl₄ / CH₂Cl₂ / -78 °C

7: K₃[Fe(CN)6], K₂CO₃; K₂OsO₂(OH)2; Na₂SO₃ / 2-methyl-propan-2-ol; H₂O

8: NaIO₄ / H₂O; ethanol

With sodium periodate; 4 A molecular sieve; K₂OsO₂(OH)2; boron trifluoride diethyl etherate; hydrogen; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; sodium sulfite; potassium hexacyanoferrate(III); palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetic acid; ethyl acetate; tert-butyl alcohol; 1: Oxidation / 2: Etherification / 3: Catalytic hydrogenation / 4: Reduction / 5: Etherification / 6: Alkylation / 7: dihydroxylation / 8: Oxidation;

DOI:10.1016/S0040-4039(99)01387-8

Reference yield:

2-(tert-butyl-diphenyl-silanyloxymethyl)-6-ethoxy-1-(toluene-4-sulfonyl)-1,6-dihydro-2H-pyridin-3-one (249928-46-9) → [(2S,5R,6S)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetaldehyde (249928-50-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / H₂ / Pd-C / ethyl acetate

2: 85 percent / NaBH₃CN / acetic acid; methanol / 0 - 20 °C

3: 91 percent / NaH; Bu₄NI / tetrahydrofuran

4: 87 percent / TiCl₄ / CH₂Cl₂ / -78 °C

5: K₃[Fe(CN)6], K₂CO₃; K₂OsO₂(OH)2; Na₂SO₃ / 2-methyl-propan-2-ol; H₂O

6: NaIO₄ / H₂O; ethanol

With sodium periodate; K₂OsO₂(OH)2; hydrogen; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; potassium carbonate; sodium sulfite; potassium hexacyanoferrate(III); palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetic acid; ethyl acetate; tert-butyl alcohol; 1: Catalytic hydrogenation / 2: Reduction / 3: Etherification / 4: Alkylation / 5: dihydroxylation / 6: Oxidation;

DOI:10.1016/S0040-4039(99)01387-8

Reference yield:

(2S,6S)-2-(tert-Butyldiphenylsilyloxymethyl)-6-hydroxy-1-tosyl-1,6-dihydropyridin-3(2H)-one (249928-45-8) → [(2S,5R,6S)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetaldehyde (249928-50-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / BF₃*OEt₂; 4 Angstroem mol. sieves / tetrahydrofuran / 0 °C

2: 91 percent / H₂ / Pd-C / ethyl acetate

3: 85 percent / NaBH₃CN / acetic acid; methanol / 0 - 20 °C

4: 91 percent / NaH; Bu₄NI / tetrahydrofuran

5: 87 percent / TiCl₄ / CH₂Cl₂ / -78 °C

6: K₃[Fe(CN)6], K₂CO₃; K₂OsO₂(OH)2; Na₂SO₃ / 2-methyl-propan-2-ol; H₂O

7: NaIO₄ / H₂O; ethanol

With sodium periodate; 4 A molecular sieve; K₂OsO₂(OH)2; boron trifluoride diethyl etherate; hydrogen; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; potassium carbonate; sodium sulfite; potassium hexacyanoferrate(III); palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetic acid; ethyl acetate; tert-butyl alcohol; 1: Etherification / 2: Catalytic hydrogenation / 3: Reduction / 4: Etherification / 5: Alkylation / 6: dihydroxylation / 7: Oxidation;

DOI:10.1016/S0040-4039(99)01387-8

upstream raw materials:

benzyl bromide

(S)-1-(furan-2-yl)-2-tert-butyldiphenylsilyloxy-N-(toluene-4-sulfonyl)ethylamine

(2S,6S)-2-(tert-Butyldiphenylsilyloxymethyl)-6-hydroxy-1-tosyl-1,6-dihydropyridin-3(2H)-one

2-(tert-butyl-diphenyl-silanyloxymethyl)-6-ethoxy-1-(toluene-4-sulfonyl)-1,6-dihydro-2H-pyridin-3-one

Downstream raw materials:

12-[(2R,5R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-1-(toluene-4-sulfonyl)-piperidin-2-yl]-dodecan-3-one

(2S,3R,6S)-3-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-[(E)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-1-(toluene-4-sulfonyl)-piperidine