(S)-4-[(2R,5R,6S)-5-Ethyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-pentanal

Base Information

• Chemical Name: (S)-4-[(2R,5R,6S)-5-Ethyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-pentanal
• CAS No.: 126421-06-5
• Molecular Formula: C₂₉H₄₀O₆
• Molecular Weight: 484.633

Synonyms:

Chemical Property of (S)-4-[(2R,5R,6S)-5-Ethyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-pentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-[(2R,5R,6S)-5-Ethyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-pentanal

There total 15 articles about (S)-4-[(2R,5R,6S)-5-Ethyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-pentanal 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:

(2S,3R)-3-Benzyloxy-5-[(4R,5S)-5-but-3-enyl-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-3-ethyl-pentan-2-ol (96823-48-2) → (S)-4-[(2R,5R,6S)-5-Ethyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-pentanal (126421-06-5)

Guidance literature:

Multi-step reaction with 15 steps

1: 1) NaH / 1) THF, DMSO, RT, 2) THF, DMSO, RT, overnight

2: 81 percent / 1N HCl / tetrahydrofuran / 7.5 h / 45 °C

3: Et₃N / CH₂Cl₂ / 2 h / 0 °C

4: K₂CO₃ / methanol / 0.5 h / Ambient temperature

5: 90 percent / DDQ / H₂O; CH₂Cl₂ / 0.33 h / 0 °C

6: 90 percent / CSA / CH₂Cl₂ / 0.25 h / 0 °C

7: 96 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / 0.5 h / Ambient temperature

8: hydrogen / Pd/C / ethanol / 72 h / Ambient temperature

9: 96 percent / NaIO₄ / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

10: 72 percent / pyridinium chlorochromate, mol. sieves 3A / CH₂Cl₂ / 0.67 h / Ambient temperature

11: 100 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

12: 83 percent / CSA / CH₂Cl₂ / 3 h / Ambient temperature

13: 1) NaH / 1) THF, DMSO, 2) THF, DMSO, RT

14: 1N HCl / methanol / 0.33 h / Ambient temperature

15: 1) DMSO, (COCl)2,2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; 3 A molecular sieve; camphor-10-sulfonic acid; hydrogen; sodium hydride; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone;

DOI:10.1248/cpb.37.1705

Reference yield:

(5S,6R,9R,10S)-9-Benzyloxy-10-(3,4-dimethoxy-benzyloxy)-9-ethyl-5-methyl-undec-1-ene-5,6-diol (96823-41-5) → (S)-4-[(2R,5R,6S)-5-Ethyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-pentanal (126421-06-5)

Guidance literature:

Multi-step reaction with 13 steps

1: Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: K₂CO₃ / methanol / 0.5 h / Ambient temperature

3: 90 percent / DDQ / H₂O; CH₂Cl₂ / 0.33 h / 0 °C

4: 90 percent / CSA / CH₂Cl₂ / 0.25 h / 0 °C

5: 96 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / 0.5 h / Ambient temperature

6: hydrogen / Pd/C / ethanol / 72 h / Ambient temperature

7: 96 percent / NaIO₄ / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

8: 72 percent / pyridinium chlorochromate, mol. sieves 3A / CH₂Cl₂ / 0.67 h / Ambient temperature

9: 100 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

10: 83 percent / CSA / CH₂Cl₂ / 3 h / Ambient temperature

11: 1) NaH / 1) THF, DMSO, 2) THF, DMSO, RT

12: 1N HCl / methanol / 0.33 h / Ambient temperature

13: 1) DMSO, (COCl)2,2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; 3 A molecular sieve; camphor-10-sulfonic acid; hydrogen; sodium hydride; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone;

DOI:10.1248/cpb.37.1705

Reference yield:

(5S,6R,9R,10S)-9-benzyloxy-9-ethyl-10-(3,4-dimethoxybenzyloxy)-5,6-<1-(4-methoxyphenyl)ethylidenedioxy>-5-methylundec-1-ene (96823-49-3) → (S)-4-[(2R,5R,6S)-5-Ethyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-pentanal (126421-06-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 81 percent / 1N HCl / tetrahydrofuran / 7.5 h / 45 °C

2: Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: K₂CO₃ / methanol / 0.5 h / Ambient temperature

4: 90 percent / DDQ / H₂O; CH₂Cl₂ / 0.33 h / 0 °C

5: 90 percent / CSA / CH₂Cl₂ / 0.25 h / 0 °C

6: 96 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / 0.5 h / Ambient temperature

7: hydrogen / Pd/C / ethanol / 72 h / Ambient temperature

8: 96 percent / NaIO₄ / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

9: 72 percent / pyridinium chlorochromate, mol. sieves 3A / CH₂Cl₂ / 0.67 h / Ambient temperature

10: 100 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

11: 83 percent / CSA / CH₂Cl₂ / 3 h / Ambient temperature

12: 1) NaH / 1) THF, DMSO, 2) THF, DMSO, RT

13: 1N HCl / methanol / 0.33 h / Ambient temperature

14: 1) DMSO, (COCl)2,2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; 3 A molecular sieve; camphor-10-sulfonic acid; hydrogen; sodium hydride; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone;

DOI:10.1248/cpb.37.1705

upstream raw materials:

(S)-4-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-4-(4-methoxybenzyloxy)pentan-1-ol

(2S,3R,6R)-3-ethyl-6-<(2S)-5-hydroxytetrahydrofuran-2-yl>-2-methyltetrahydropyran-3-ol

(2S,3R)-3-Benzyloxy-5-[(4R,5S)-5-but-3-enyl-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-3-ethyl-pentan-2-ol

(5S,6R,9R,10S)-9-Benzyloxy-10-(3,4-dimethoxy-benzyloxy)-9-ethyl-5-methyl-undec-1-ene-5,6-diol

Downstream raw materials:

(E)-(S)-6-[(2R,5R,6S)-5-Ethyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-6-(4-methoxy-benzyloxy)-hept-2-enoic acid ethyl ester

(S)-1-<(2R,5S)-5-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-5-methyltetrahydrofuran-2-yl>ethane-1,2-diol

(2E,6S)-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)hept-2-en-1-ol

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