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

Base Information

• Chemical Name: 4-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-1-(4-methoxy-benzyloxy)-pent-4-en-2-ol
• CAS No.: 312695-81-1
• Molecular Formula: C₃₀H₅₀O₅Si
• Molecular Weight: 518.809
• Mol file: 312695-81-1.mol

Synonyms:4-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-1-(4-methoxy-benzyloxy)-pent-4-en-2-ol

Chemical Property of 4-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-1-(4-methoxy-benzyloxy)-pent-4-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-1-(4-methoxy-benzyloxy)-pent-4-en-2-ol

There total 45 articles about 4-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-1-(4-methoxy-benzyloxy)-pent-4-en-2-ol 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: 72.0%

C50H64O10SSi → 4-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-1-(4-methoxy-benzyloxy)-pent-4-en-2-ol (312695-81-1)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In methanol; at -20 - 23 ℃;

DOI:10.1021/ja0027416

Reference yield:

(2R,6S)-tert-butyl-(2-{6-[(2R)-3-iodo-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-dimethyl-silane (312695-78-6) → 4-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-1-(4-methoxy-benzyloxy)-pent-4-en-2-ol (312695-81-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide; various solvent(s) / 0.25 h / 0 °C

1.2: 89 percent / dimethylformamide / 12 h / 60 °C

2.1: Red-Al / tetrahydrofuran / 0.17 h / 0 °C

3.1: Et₃N; DMAP / CH₂Cl₂ / 12 h / 23 °C

4.1: 3.61 g / sodium amalgam; Na₂HPO₄ / methanol / -20 - 23 °C

With dmap; disodium hydrogenphosphate; sodium amalgam; sodium hydride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo010854h

Reference yield:

(2R)-3-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methylpropan-1-ol (312695-90-2) → 4-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-1-(4-methoxy-benzyloxy)-pent-4-en-2-ol (312695-81-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 96 percent / I₂; imidazole; PPh₃ / diethyl ether; acetonitrile / 0.5 h / 0 °C

2.1: NaH / dimethylformamide; various solvent(s) / 0.25 h / 0 °C

2.2: 89 percent / dimethylformamide / 12 h / 60 °C

3.1: Red-Al / tetrahydrofuran / 0.17 h / 0 °C

4.1: Et₃N; DMAP / CH₂Cl₂ / 12 h / 23 °C

5.1: 3.61 g / sodium amalgam; Na₂HPO₄ / methanol / -20 - 23 °C

With 1H-imidazole; dmap; disodium hydrogenphosphate; sodium amalgam; iodine; sodium hydride; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo010854h

upstream raw materials:

(iodomethyl)magnesium chloride

(2S,4RS,6R)-4-benzenesulfonyl-7-{(2R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-1-(4-methoxybenzyloxy)-6-methylheptan-2-ol

[(2R,4S)-4-(1-Ethoxy-allyloxy)-2-methyl-hept-6-enyloxymethyl]-benzene

[3R]-4-Benzyloxy-3-methylbutanal

Downstream raw materials:

(2R,6R)-tert-butyl-[2-(6-{4-[(2S)-3-(4-methoxybenzyloxy)-2-methoxymethoxy-propyl]-[(2S)-2-methylpent-4-enyl]}-5,6-dihydro-2H-pyran-2-yl)-ethoxy]-dimethylsilane

laulimalide

(Z)-(1R,3S,7S,8S,10S,12S,18R)-7-Hydroxy-12-[(E)-(S)-1-(4-methoxy-benzyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-3-methyl-5-methylene-9,13,22-trioxa-tricyclo[16.3.1.0^8,10]docosa-15,19-dien-14-one

(E)-(1R,7S,11S,15S,17R)-7-[(E)-(S)-1-(4-Methoxy-benzyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-11-methoxymethoxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-9,19-dien-3-yn-5-one