[(4S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid phenyl ester

Base Information

• Chemical Name: [(4S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid phenyl ester
• CAS No.: 224968-30-3
• Molecular Formula: C₂₅H₃₂O₅
• Molecular Weight: 412.526
• Mol file: 224968-30-3.mol

Synonyms:[(4S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid phenyl ester

Chemical Property of [(4S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(4S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid phenyl ester

There total 7 articles about [(4S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid phenyl ester 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)-5-Benzyloxy-3-hydroxy-4,4-dimethyl-1-phenyl-pentan-1-one (212050-32-3) → [(4S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid phenyl ester (224968-30-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 73 percent / m-chloroperoxybenzoic acid, NaH₂PO₄ / 1,2-dichloro-ethane / 50 h / 40 °C

2: 435 mg / diisopropylethylamine / CH₂Cl₂ / 0.75 h / 0 °C

3: 300 mg / diisobutylaluminum hydride / CH₂Cl₂ / 1 h / -78 °C

4: PCC, Celite / CH₂Cl₂ / 5 h

5: 1.) potassium bis(trimethylsilyl)amide, water, LaLi₃tris((S)-binaphthoxide) / 1.) THF, toluene, -20 deg C, 30 min, 2.) THF, toluene, -20 deg C, 24 h

6: 20.5 mg / 4 Angstroem molecular sieves, racemic trans-N,N'-bis(p-toluenesulfonyl)cyclohexane-1,2-diamine, bis(trimethylsilyl)peroxide, SnCl₄ / CH₂Cl₂ / 6 h / 0 °C

7: 9 mg / camphorsulfonic acid, 70 percent hydrogen fluoride-pyridine / CH₂Cl₂ / 0.5 h

With sodium dihydrogenphosphate; bis-trimethylsilanyl peroxide; LaLi₃ tris((S)-binaphthoxide); racemic trans-N,N'-bis(p-toluenesulfonyl)cyclohexane-1,2-diamine; 4 A molecular sieve; Celite; camphor-10-sulfonic acid; water; tin(IV) chloride; potassium hexamethylsilazane; diisobutylaluminium hydride; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/ja990031y

Reference yield:

phenyl (S)-5-benzyloxy-3-hydroxy-4,4-dimethylpentanoate (224968-18-7) → [(4S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid phenyl ester (224968-30-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 435 mg / diisopropylethylamine / CH₂Cl₂ / 0.75 h / 0 °C

2: 300 mg / diisobutylaluminum hydride / CH₂Cl₂ / 1 h / -78 °C

3: PCC, Celite / CH₂Cl₂ / 5 h

4: 1.) potassium bis(trimethylsilyl)amide, water, LaLi₃tris((S)-binaphthoxide) / 1.) THF, toluene, -20 deg C, 30 min, 2.) THF, toluene, -20 deg C, 24 h

5: 20.5 mg / 4 Angstroem molecular sieves, racemic trans-N,N'-bis(p-toluenesulfonyl)cyclohexane-1,2-diamine, bis(trimethylsilyl)peroxide, SnCl₄ / CH₂Cl₂ / 6 h / 0 °C

6: 9 mg / camphorsulfonic acid, 70 percent hydrogen fluoride-pyridine / CH₂Cl₂ / 0.5 h

With bis-trimethylsilanyl peroxide; LaLi₃ tris((S)-binaphthoxide); racemic trans-N,N'-bis(p-toluenesulfonyl)cyclohexane-1,2-diamine; 4 A molecular sieve; Celite; camphor-10-sulfonic acid; water; tin(IV) chloride; potassium hexamethylsilazane; diisobutylaluminium hydride; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In dichloromethane;

DOI:10.1021/ja990031y

Reference yield:

5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentan-1-ol (224968-25-6) → [(4S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid phenyl ester (224968-30-3)

Guidance literature:

Multi-step reaction with 4 steps

1: PCC, Celite / CH₂Cl₂ / 5 h

2: 1.) potassium bis(trimethylsilyl)amide, water, LaLi₃tris((S)-binaphthoxide) / 1.) THF, toluene, -20 deg C, 30 min, 2.) THF, toluene, -20 deg C, 24 h

3: 20.5 mg / 4 Angstroem molecular sieves, racemic trans-N,N'-bis(p-toluenesulfonyl)cyclohexane-1,2-diamine, bis(trimethylsilyl)peroxide, SnCl₄ / CH₂Cl₂ / 6 h / 0 °C

4: 9 mg / camphorsulfonic acid, 70 percent hydrogen fluoride-pyridine / CH₂Cl₂ / 0.5 h

With bis-trimethylsilanyl peroxide; LaLi₃ tris((S)-binaphthoxide); racemic trans-N,N'-bis(p-toluenesulfonyl)cyclohexane-1,2-diamine; 4 A molecular sieve; Celite; camphor-10-sulfonic acid; water; tin(IV) chloride; potassium hexamethylsilazane; pyridine hydrogenfluoride; pyridinium chlorochromate; In dichloromethane;

DOI:10.1021/ja990031y

upstream raw materials:

2,2-dimethoxy-propane

(3S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6,6-dimethyl-heptanoic acid phenyl ester

(S)-5-Benzyloxy-3-hydroxy-4,4-dimethyl-1-phenyl-pentan-1-one

(S)-5-benzyloxy-3-(tert-butyldimethylsiloxy)-4,4-dimethyl-1-pentanal

Downstream raw materials:

2-<(4R,6S)-6-(2-benzyloxy-1,1-dimethylethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethanol