(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

Base Information

Chemical Name:(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
CAS No.:625125-06-6
Molecular Formula:C₃₉H₅₈O₈Si
Molecular Weight:682.97
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 5 articles about (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 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: 78.0%

: 625125-12-4
(2S)-2-benzyloxy-6-hydroxy-4-oxo-7-[(2R,4R,6R)-(2-phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)]heptyl 2,2-dimethylpropionate

: 625125-06-6
(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

Guidance literature:: With Dess-Martin periodane; In tetrahydrofuran; dichloromethane; water; for 8h;
DOI:10.1021/ja030316h

Reference yield:

: 1026521-40-3
(S)-4-(2-Methyl-allyl)-2-phenyl-[1,3]dioxolane

: 625125-06-6
(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

Guidance literature:: Multi-step reaction with 4 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

4.1: 78 percent / Dess-Martin reagent / CH₂Cl₂; tetrahydrofuran; H₂O / 8 h

With sodium periodate; osmium(VIII) oxide; diisobutylaluminium hydride; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; toluene;
DOI:10.1021/ja030316h

Reference yield:

: 226703-84-0
(2S)-1-{[t-butyl(dimethyl)silyl]oxy}-4-methylpent-4-en-2-ol

: 625125-06-6
(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

Guidance literature:: Multi-step reaction with 5 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

5.1: 78 percent / Dess-Martin reagent / CH₂Cl₂; tetrahydrofuran; H₂O / 8 h

With sodium periodate; osmium(VIII) oxide; camphor-10-sulfonic acid; diisobutylaluminium hydride; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja030316h