((S)-5-{(2R,6R)-6-[4-(4-Methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-4-methyl-2-methylene-pentyl)-trimethyl-silane

Base Information

• Chemical Name: ((S)-5-{(2R,6R)-6-[4-(4-Methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-4-methyl-2-methylene-pentyl)-trimethyl-silane
• CAS No.: 464914-01-0
• Molecular Formula: C₂₇H₄₀O₃Si
• Molecular Weight: 440.698
• Mol file: 464914-01-0.mol

Synonyms:((S)-5-{(2R,6R)-6-[4-(4-Methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-4-methyl-2-methylene-pentyl)-trimethyl-silane

Chemical Property of ((S)-5-{(2R,6R)-6-[4-(4-Methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-4-methyl-2-methylene-pentyl)-trimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((S)-5-{(2R,6R)-6-[4-(4-Methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-4-methyl-2-methylene-pentyl)-trimethyl-silane

There total 4 articles about ((S)-5-{(2R,6R)-6-[4-(4-Methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-4-methyl-2-methylene-pentyl)-trimethyl-silane 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:

methyl (3R)-3-methyl-5-oxopentanoate (79936-62-2) → ((S)-5-{(2R,6R)-6-[4-(4-Methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-4-methyl-2-methylene-pentyl)-trimethyl-silane (464914-01-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Jacobsen catalyst / various solvent(s) / -25 °C

1.2: TFA / CH₂Cl₂

2.1: 94 percent / CeCl₃*7H₂O; NaBH₄ / methanol / -78 °C

3.1: 91 percent / iPr₂NEt / CH₂Cl₂

4.1: BF₃*OEt₂ / CH₂Cl₂ / -20 °C

4.2: CeCl₃ / tetrahydrofuran / -78 °C

With sodium tetrahydroborate; cerium(III) chloride; boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; (S,S)-chloro[2,2'-[1,2-cyclohexanediylbis(nitrilomethylidyne)]bis-[4,6-bis(1,1-dimethylethyl)phenolato]]^(2-)-N,N',O,O'-manganese; In methanol; dichloromethane; 1.1: hetero-Diels-Alder cycloaddition / 2.1: Luche reduction;

DOI:10.1016/S0040-4039(02)00907-3

Reference yield:

(trimethylsilyl)methylmagnesium chloride (13170-43-9) + (R)-4-((2R,4S)-4-Acetoxy-3,4-dihydro-2H-pyran-2-yl)-3-methyl-butyric acid methyl ester (464914-02-1) + tributyl-[1-(4-methoxy-benzyloxymethyl)-propa-1,2-dienyl]-stannane → ((S)-5-{(2R,6R)-6-[4-(4-Methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-4-methyl-2-methylene-pentyl)-trimethyl-silane (464914-01-0)

Guidance literature:

(R)-4-((2R,4S)-4-Acetoxy-3,4-dihydro-2H-pyran-2-yl)-3-methyl-butyric acid methyl ester; tributyl-[1-(4-methoxy-benzyloxymethyl)-propa-1,2-dienyl]-stannane; With boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃;

(trimethylsilyl)methylmagnesium chloride; With cerium(III) chloride; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(02)00907-3

Reference yield:

(R)-3-Methyl-4-((R)-4-oxo-3,4-dihydro-2H-pyran-2-yl)-butyric acid methyl ester (438222-46-9) → ((S)-5-{(2R,6R)-6-[4-(4-Methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-4-methyl-2-methylene-pentyl)-trimethyl-silane (464914-01-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 94 percent / CeCl₃*7H₂O; NaBH₄ / methanol / -78 °C

2.1: 91 percent / iPr₂NEt / CH₂Cl₂

3.1: BF₃*OEt₂ / CH₂Cl₂ / -20 °C

3.2: CeCl₃ / tetrahydrofuran / -78 °C

With sodium tetrahydroborate; cerium(III) chloride; boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; 1.1: Luche reduction;

DOI:10.1016/S0040-4039(02)00907-3

upstream raw materials:

(trimethylsilyl)methylmagnesium chloride

(R)-4-((2R,4S)-4-Acetoxy-3,4-dihydro-2H-pyran-2-yl)-3-methyl-butyric acid methyl ester

methyl (3R)-3-methyl-5-oxopentanoate

(R)-3-Methyl-4-((R)-4-oxo-3,4-dihydro-2H-pyran-2-yl)-butyric acid methyl ester

Downstream raw materials:

C₅₈H₈₈O₉Si₂

1-{3-[3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-5-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-pent-4-enyl]-oxiranyl}-3-(3-{6-[4-(4-methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-but-3-en-1-ol