(2S)-2-benzyloxy-6-hydroxy-4-oxo-7-[(2R,4R,6R)-(2-phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)]heptyl 2,2-dimethylpropionate

Base Information

• Chemical Name: (2S)-2-benzyloxy-6-hydroxy-4-oxo-7-[(2R,4R,6R)-(2-phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)]heptyl 2,2-dimethylpropionate
• CAS No.: 625125-12-4
• Molecular Formula: C₃₉H₆₀O₈Si
• Molecular Weight: 684.986
• Mol file: 625125-12-4.mol

Synonyms:(2S)-2-benzyloxy-6-hydroxy-4-oxo-7-[(2R,4R,6R)-(2-phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)]heptyl 2,2-dimethylpropionate

Chemical Property of (2S)-2-benzyloxy-6-hydroxy-4-oxo-7-[(2R,4R,6R)-(2-phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)]heptyl 2,2-dimethylpropionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-benzyloxy-6-hydroxy-4-oxo-7-[(2R,4R,6R)-(2-phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)]heptyl 2,2-dimethylpropionate

There total 4 articles about (2S)-2-benzyloxy-6-hydroxy-4-oxo-7-[(2R,4R,6R)-(2-phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)]heptyl 2,2-dimethylpropionate 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: 67.0%

((2R,4S,6R)-2-Phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)-acetaldehyde (251641-49-3) + (2S)-2-benzyloxy-4-oxo-pentyl 2,2-dimethylpropionate (625125-09-9) → (2S)-2-benzyloxy-6-hydroxy-4-oxo-7-[(2R,4R,6R)-(2-phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)]heptyl 2,2-dimethylpropionate (625125-12-4)

Guidance literature:

(2S)-2-benzyloxy-4-oxo-pentyl 2,2-dimethylpropionate; With lithium diisopropyl amide; In tetrahydrofuran; hexane; for 0.5h;

((2R,4S,6R)-2-Phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)-acetaldehyde; In tetrahydrofuran; hexane; for 0.25h;

DOI:10.1021/ja030316h

Reference yield:

(S)-4-(2-Methyl-allyl)-2-phenyl-[1,3]dioxolane (1026521-40-3) → (2S)-2-benzyloxy-6-hydroxy-4-oxo-7-[(2R,4R,6R)-(2-phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)]heptyl 2,2-dimethylpropionate (625125-12-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / CH₂Cl₂; toluene / 16 h / -78 - 20 °C

1.2: Et₃N; DMAP / CH₂Cl₂ / 1 h

2.1: 30.1 g / OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 16 h

3.1: LDA / tetrahydrofuran; hexane / 0.5 h

3.2: 67 percent / tetrahydrofuran; hexane / 0.25 h

With sodium periodate; osmium(VIII) oxide; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; toluene;

DOI:10.1021/ja030316h

Reference yield:

(2S)-1-{[t-butyl(dimethyl)silyl]oxy}-4-methylpent-4-en-2-ol (226703-84-0) → (2S)-2-benzyloxy-6-hydroxy-4-oxo-7-[(2R,4R,6R)-(2-phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)]heptyl 2,2-dimethylpropionate (625125-12-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: camphorsulfonic acid / methanol; dimethylformamide / 16 h

2.1: diisobutylaluminium hydride / CH₂Cl₂; toluene / 16 h / -78 - 20 °C

2.2: Et₃N; DMAP / CH₂Cl₂ / 1 h

3.1: 30.1 g / OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 16 h

4.1: LDA / tetrahydrofuran; hexane / 0.5 h

4.2: 67 percent / tetrahydrofuran; hexane / 0.25 h

With sodium periodate; osmium(VIII) oxide; camphor-10-sulfonic acid; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja030316h

upstream raw materials:

((2R,4S,6R)-2-Phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)-acetaldehyde

(2S)-2-benzyloxy-4-oxo-pentyl 2,2-dimethylpropionate

(S)-4-(2-Methyl-allyl)-2-phenyl-[1,3]dioxolane

(2S)-1-{[t-butyl(dimethyl)silyl]oxy}-4-methylpent-4-en-2-ol

Downstream raw materials:

(6S)-6-benzyloxy-4-hydroxy-6-oxo-7-[(2R,4S,6R)-(2-phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)]hept-4-enyl-2,2-dimethylpropionate