(S)-4-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pentanal

Base Information

• Chemical Name: (S)-4-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pentanal
• CAS No.: 203630-36-8
• Molecular Formula: C₂₂H₃₄O₄
• Molecular Weight: 362.51
• Mol file: 203630-36-8.mol

Synonyms:(S)-4-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pentanal

Chemical Property of (S)-4-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pentanal

There total 13 articles about (S)-4-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-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:

(S)-4-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pentanoic acid ethyl ester → (S)-4-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pentanal (203630-36-8)

Guidance literature:

With diisobutylaluminium hydride; In pentane; at -100 ℃; for 1h; Yield given;

DOI:10.1016/S0040-4039(97)10782-1

Reference yield:

(2R,3S,4S)-5-benzyloxy-2,3-epoxy-4-methyl-1-pentanol (73814-75-2,73814-80-9,73837-43-1,79027-31-9,81520-04-9,81520-05-0,81520-09-4,104320-78-7,115458-81-6,115458-82-7,125873-79-2,125873-80-5,81520-08-3) → (S)-4-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pentanal (203630-36-8)

Guidance literature:

Multi-step reaction with 13 steps

1: (COCl)2/DMSO, Et₃N / CH₂Cl₂ / -78 °C

2: 1.) NaH / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 1.5 h

3: 95 percent / 1,2-dichloro-ethane; H₂O; hexane / -30 °C

4: DMAP, imidazole / dimethylformamide / 2 h / 40 °C

5: i-Bu₂AlH / hexane; CH₂Cl₂ / 1.5 h / -78 °C

6: MCPBA / CH₂Cl₂ / 1 h / -10 °C

7: (COCl)2/DMSO, Et₃N / CH₂Cl₂ / -78 °C

8: 1.) NaH / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 1.5 h

9: TBAF / tetrahydrofuran / 1 h / 0 °C

10: 85 percent / 1,2-dichloro-ethane; H₂O; hexane / 6 h / -30 °C

11: PPTS / diethyl ether / 1.5 h

12: H₂ / Rh/Al₂O₃ / ethanol / 5 h

13: i-Bu₂AlH / pentane / 1 h / -100 °C

With 1H-imidazole; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; Rh/Al₂O₃; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; pentane;

DOI:10.1016/S0040-4039(97)10782-1

Reference yield:

(E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate (155430-43-6) → (S)-4-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pentanal (203630-36-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 95 percent / 1,2-dichloro-ethane; H₂O; hexane / -30 °C

2: DMAP, imidazole / dimethylformamide / 2 h / 40 °C

3: i-Bu₂AlH / hexane; CH₂Cl₂ / 1.5 h / -78 °C

4: MCPBA / CH₂Cl₂ / 1 h / -10 °C

5: (COCl)2/DMSO, Et₃N / CH₂Cl₂ / -78 °C

6: 1.) NaH / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 1.5 h

7: TBAF / tetrahydrofuran / 1 h / 0 °C

8: 85 percent / 1,2-dichloro-ethane; H₂O; hexane / 6 h / -30 °C

9: PPTS / diethyl ether / 1.5 h

10: H₂ / Rh/Al₂O₃ / ethanol / 5 h

11: i-Bu₂AlH / pentane / 1 h / -100 °C

With 1H-imidazole; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; Rh/Al₂O₃; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; pentane;

DOI:10.1016/S0040-4039(97)10782-1

upstream raw materials:

(2R,3S,4S)-5-benzyloxy-2,3-epoxy-4-methyl-1-pentanol

(2S,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxirane-2-carbaldehyde

(E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate

(E)-(4S,5R,6S)-7-benzyloxy-5-triethylsilyloxy-4,6-dimethyl-2-hepten-1-ol

Downstream raw materials:

(3R,4S,7S)-7-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-3-methyl-oct-1-en-4-ol

(3S,4S,5R,6S,9S)-9-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-dec-1-en-4-ol

(3R,4R,5R,6S,9S)-9-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-dec-1-en-4-ol

(4S,5S,6S)-4-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-6-[(1S,4S,5S,6R,7R)-6-methoxy-4-(4-methoxy-benzyloxy)-1,5,7-trimethyl-9-triisopropylsilanyloxy-nonyl]-5-methyl-[1,3,2]dioxasilinane