(3S,5R,8R,9S,11S,15S,16R,17S)-16-O-<(t-butyldimethylsilyloxy)methyl>-3,5:8,9:15,17-tri-O-isopropylidene-1-O-(4-methoxybenzyl)-11-O-<(2-methoxyethoxy)methyl>-13,13-bis(methylthio)-18-nonadecene-1,3,5,8,9,11,15,17-octol

Base Information

• Chemical Name: (3S,5R,8R,9S,11S,15S,16R,17S)-16-O-<(t-butyldimethylsilyloxy)methyl>-3,5:8,9:15,17-tri-O-isopropylidene-1-O-(4-methoxybenzyl)-11-O-<(2-methoxyethoxy)methyl>-13,13-bis(methylthio)-18-nonadecene-1,3,5,8,9,11,15,17-octol
• CAS No.: 119178-87-9
• Molecular Formula: C₄₉H₈₆O₁₂S₂Si
• Molecular Weight: 959.432

Synonyms:(3S,5R,8R,9S,11S,15S,16R,17S)-16-O-<(t-butyldimethylsilyloxy)methyl>-3,5:8,9:15,17-tri-O-isopropylidene-1-O-(4-methoxybenzyl)-11-O-<(2-methoxyethoxy)methyl>-13,13-bis(methylthio)-18-nonadecene-1,3,5,8,9,11,15,17-octol

Chemical Property of (3S,5R,8R,9S,11S,15S,16R,17S)-16-O-<(t-butyldimethylsilyloxy)methyl>-3,5:8,9:15,17-tri-O-isopropylidene-1-O-(4-methoxybenzyl)-11-O-<(2-methoxyethoxy)methyl>-13,13-bis(methylthio)-18-nonadecene-1,3,5,8,9,11,15,17-octol

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of (3S,5R,8R,9S,11S,15S,16R,17S)-16-O-<(t-butyldimethylsilyloxy)methyl>-3,5:8,9:15,17-tri-O-isopropylidene-1-O-(4-methoxybenzyl)-11-O-<(2-methoxyethoxy)methyl>-13,13-bis(methylthio)-18-nonadecene-1,3,5,8,9,11,15,17-octol

There total 3 articles about (3S,5R,8R,9S,11S,15S,16R,17S)-16-O-<(t-butyldimethylsilyloxy)methyl>-3,5:8,9:15,17-tri-O-isopropylidene-1-O-(4-methoxybenzyl)-11-O-<(2-methoxyethoxy)methyl>-13,13-bis(methylthio)-18-nonadecene-1,3,5,8,9,11,15,17-octol 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: 84.0%

(3S,4R,5S)-4-<(t-butyldimethylsilyloxy)methyl>3,5-O-isopropylidene-1-trimethylstannyl-1,1-bis(methylthio)-6-heptene-3,5-diol + (3S,5R,8R,9R,11S)-12-iodo-3,5:8,9-di-O-isopropylidene-1-O-(4-methoxybenzyl)-11-O-<(2-methoxyethoxy)methyl>-1,3,5,8,9,11-dodecanehexol → (3S,5R,8R,9S,11S,15S,16R,17S)-16-O-<(t-butyldimethylsilyloxy)methyl>-3,5:8,9:15,17-tri-O-isopropylidene-1-O-(4-methoxybenzyl)-11-O-<(2-methoxyethoxy)methyl>-13,13-bis(methylthio)-18-nonadecene-1,3,5,8,9,11,15,17-octol (119178-87-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -29 ℃;

DOI:10.1246/bcsj.61.2147

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (3S,5R,8R,9S,11S,15S,16R,17S)-16-O-<(t-butyldimethylsilyloxy)methyl>-3,5:8,9:15,17-tri-O-isopropylidene-1-O-(4-methoxybenzyl)-11-O-<(2-methoxyethoxy)methyl>-13,13-bis(methylthio)-18-nonadecene-1,3,5,8,9,11,15,17-octol (119178-87-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / NaH / dimethylformamide / 15 h / 25 °C

2: 86 percent / H₂ / Raney Ni W-4 / ethanol / 6 h / 20 °C

3: 99.4 percent / iodine, triphenylphosphine, imidazole / benzene / 0.5 h / 25 °C

4: 84 percent / n-BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / -29 °C

With 1H-imidazole; n-butyllithium; hydrogen; iodine; sodium hydride; triphenylphosphine; Raney Ni W-4; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; N,N-dimethyl-formamide; benzene;

DOI:10.1246/bcsj.61.2147

Reference yield:

(2S,4R,5R,8S,10S)-4,5:8,10-di-O-isopropylidene-12-O-(4-methoxybenzyl)-2-O-<(2-methoxyethoxy)methyl>-1,2,4,5,8,10,12-dodecaneheptol → (3S,5R,8R,9S,11S,15S,16R,17S)-16-O-<(t-butyldimethylsilyloxy)methyl>-3,5:8,9:15,17-tri-O-isopropylidene-1-O-(4-methoxybenzyl)-11-O-<(2-methoxyethoxy)methyl>-13,13-bis(methylthio)-18-nonadecene-1,3,5,8,9,11,15,17-octol (119178-87-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 99.4 percent / iodine, triphenylphosphine, imidazole / benzene / 0.5 h / 25 °C

2: 84 percent / n-BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / -29 °C

With 1H-imidazole; n-butyllithium; iodine; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; benzene;

DOI:10.1246/bcsj.61.2147

upstream raw materials:

p-methoxybenzyl chloride

Downstream raw materials:

C₄₉H₈₈O₁₃S₂Si

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