(⁽⁵⁾-((4S,5R)-S-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methoxy)(tert-butyl)dimethylsilane

Base Information

• Chemical Name: (⁽⁵⁾-((4S,5R)-S-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methoxy)(tert-butyl)dimethylsilane
• CAS No.: 887927-61-9
• Molecular Formula: C₂₅H₄₂O₅Si
• Molecular Weight: 450.691

Synonyms:(⁽⁵⁾-((4S,5R)-S-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methoxy)(tert-butyl)dimethylsilane

Chemical Property of (⁽⁵⁾-((4S,5R)-S-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methoxy)(tert-butyl)dimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (⁽⁵⁾-((4S,5R)-S-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methoxy)(tert-butyl)dimethylsilane

There total 7 articles about (⁽⁵⁾-((4S,5R)-S-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methoxy)(tert-butyl)dimethylsilane 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: 97.0%

(S)-1-((4R,5S)-5-((S)-(tert-butyldimethylsilyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-en-1-ol (868761-58-4) + chloromethyl methyl ether (107-30-2) → ((5)-((4S,5R)-S-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methoxy)(tert-butyl)dimethylsilane (887927-61-9)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 40 ℃; for 3.5h;

DOI:10.1021/jo060159f

Reference yield:

(4S,5S)-5-benzoyl-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide (868761-55-1) → ((5)-((4S,5R)-S-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methoxy)(tert-butyl)dimethylsilane (887927-61-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1.5 h / -78 °C

2: 98 percent / DMAP; imidazole / dimethylformamide / 6 h / 20 °C

3: 93 percent / tetrahydrofuran / 0.5 h / -10 °C

4: 89 percent / L-Selectride / tetrahydrofuran / 1 h / -78 °C

5: 97 percent / DMAP; ethyldiisopropylamine / CH₂Cl₂ / 3.5 h / 40 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; cerium(III) chloride; L-Selectride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo060159f

Reference yield:

(4S,5R)-5-((S)-hydroxy(phenyl)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide (887927-67-5) → ((5)-((4S,5R)-S-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methoxy)(tert-butyl)dimethylsilane (887927-61-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / DMAP; imidazole / dimethylformamide / 6 h / 20 °C

2: 93 percent / tetrahydrofuran / 0.5 h / -10 °C

3: 89 percent / L-Selectride / tetrahydrofuran / 1 h / -78 °C

4: 97 percent / DMAP; ethyldiisopropylamine / CH₂Cl₂ / 3.5 h / 40 °C

With 1H-imidazole; dmap; L-Selectride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo060159f

upstream raw materials:

(S)-1-((4R,5S)-5-((S)-(tert-butyldimethylsilyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-en-1-ol

chloromethyl methyl ether

(4S,5S)-5-benzoyl-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide

(4S,5R)-5-((S)-hydroxy(phenyl)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide

Downstream raw materials:

(S)-((4S,5R)-5-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methyl 4-methylbenzenesulfonate

(2S,3S,4S,5R)-2-(but-3-enyl)-3,4-bis-tert-butyldimethylsilyloxy-tetrahydro-5-phenylfuran

(2S,3S,4S,5R)-2-(but-3-enyl)-tetrahydro-5-phenylfuran-3,4-diol

(S)-((4R,5R)-5-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methanol

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