1-(S)-[5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl]-3-triisopropylsilyl-prop-2-yn-1-yl-methoxymethyl ether

Base Information

• Chemical Name: 1-(S)-[5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl]-3-triisopropylsilyl-prop-2-yn-1-yl-methoxymethyl ether
• CAS No.: 790698-02-1
• Molecular Formula: C₂₆H₄₀O₄Si
• Molecular Weight: 444.687

Synonyms:1-(S)-[5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl]-3-triisopropylsilyl-prop-2-yn-1-yl-methoxymethyl ether

Chemical Property of 1-(S)-[5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl]-3-triisopropylsilyl-prop-2-yn-1-yl-methoxymethyl ether

Chemical Property:

Purity/Quality:

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Technology Process of 1-(S)-[5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl]-3-triisopropylsilyl-prop-2-yn-1-yl-methoxymethyl ether

There total 9 articles about 1-(S)-[5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl]-3-triisopropylsilyl-prop-2-yn-1-yl-methoxymethyl ether 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: 99.0%

{4-(S)-[1-(S)-benzyloxymethyl-allyloxy]-3-(S)-methoxymethoxy-hex-5-en-1-ynyl}triisopropylsilane (790698-01-0) → 1-(S)-[5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl]-3-triisopropylsilyl-prop-2-yn-1-yl-methoxymethyl ether (790698-02-1)

Guidance literature:

With Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; In dichloromethane; for 8h; Heating;

DOI:10.1021/ja0455852

Reference yield:

(S)-1-(benzyloxy)but-3-en-2-ol (109613-59-4) → 1-(S)-[5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl]-3-triisopropylsilyl-prop-2-yn-1-yl-methoxymethyl ether (790698-02-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 °C

1.2: 98 percent / tetrahydrofuran / 0 - 20 °C

2.1: Et₃N; pivaloyl chloride / diethyl ether / 1 h / 0 °C

2.2: 78 percent / n-BuLi / tetrahydrofuran; hexane; diethyl ether / 2 h / 0 °C

3.1: 91 percent / 4-(dimethylamino)-pyridine; DIEA / CH₂Cl₂ / 72 h / 20 °C

4.1: 92 percent / LiBH₄; MeOH / diethyl ether / 2 h / 0 °C

5.1: oxalyl chloride; dimethylsulfoxide; DIEA / CH₂Cl₂ / 0.25 h / -78 - 0 °C

6.1: t-BuOK / tetrahydrofuran; toluene / 1 h / 0 °C

6.2: 91 percent / tetrahydrofuran; toluene / 2 h / 20 °C

7.1: 99 percent / Cl₂(Cy₃P)(IMes)Ru=CHPh / CH₂Cl₂ / 8 h / Heating

With methanol; dmap; lithium borohydride; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; oxalyl dichloride; potassium tert-butylate; pivaloyl chloride; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 6.1: Swern oxidation;

DOI:10.1021/ja0455852

Reference yield:

(S)-benzyl glycidyl ether (2930-05-4,14618-80-5,89616-40-0,16495-13-9) → 1-(S)-[5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl]-3-triisopropylsilyl-prop-2-yn-1-yl-methoxymethyl ether (790698-02-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 99 percent / n-BuLi / tetrahydrofuran / -10 - 25 °C

2.1: NaH / tetrahydrofuran / 1 h / 0 °C

2.2: 98 percent / tetrahydrofuran / 0 - 20 °C

3.1: Et₃N; pivaloyl chloride / diethyl ether / 1 h / 0 °C

3.2: 78 percent / n-BuLi / tetrahydrofuran; hexane; diethyl ether / 2 h / 0 °C

4.1: 91 percent / 4-(dimethylamino)-pyridine; DIEA / CH₂Cl₂ / 72 h / 20 °C

5.1: 92 percent / LiBH₄; MeOH / diethyl ether / 2 h / 0 °C

6.1: oxalyl chloride; dimethylsulfoxide; DIEA / CH₂Cl₂ / 0.25 h / -78 - 0 °C

7.1: t-BuOK / tetrahydrofuran; toluene / 1 h / 0 °C

7.2: 91 percent / tetrahydrofuran; toluene / 2 h / 20 °C

8.1: 99 percent / Cl₂(Cy₃P)(IMes)Ru=CHPh / CH₂Cl₂ / 8 h / Heating

With methanol; dmap; lithium borohydride; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; n-butyllithium; oxalyl dichloride; potassium tert-butylate; pivaloyl chloride; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 7.1: Swern oxidation;

DOI:10.1021/ja0455852

upstream raw materials:

{4-(S)-[1-(S)-benzyloxymethyl-allyloxy]-3-(S)-methoxymethoxy-hex-5-en-1-ynyl}triisopropylsilane

(S)-1-(benzyloxy)but-3-en-2-ol

(S)-benzyl glycidyl ether

4-(S)-benzyl-3-{2-[1-(S)-benzyloxymethyl-allyloxy]acetyl}oxazolidin-2-one

Downstream raw materials:

(+)-gigantecin

4-(5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl)-4-(S)-methoxymethoxy-1-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-yn-1-(R)-ol

2-(S)-benzyloxymethyl-5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-ynyl}-2,5-dihydrofuran

3-[7-(5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]butyl}tetrahydrofuran-2-(S)-yl)-2-(R)-(4-methoxybenzyloxy)hept-3-en-5-ynyl]-5-(S)-methyl-5H-furan-2-one

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