(2S,6R,7S,8S)-(1'Z)-2-(benzyloxymethyloxymethyl)-7-(4'-trimethylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo [5.4.1^6,8.0]undecane

Base Information

• Chemical Name: (2S,6R,7S,8S)-(1'Z)-2-(benzyloxymethyloxymethyl)-7-(4'-trimethylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo [5.4.1^6,8.0]undecane
• CAS No.: 460710-27-4
• Molecular Formula: C₂₆H₃₇NO₃Si
• Molecular Weight: 439.67

Synonyms:(2S,6R,7S,8S)-(1'Z)-2-(benzyloxymethyloxymethyl)-7-(4'-trimethylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo [5.4.1^6,8.0]undecane

Chemical Property of (2S,6R,7S,8S)-(1'Z)-2-(benzyloxymethyloxymethyl)-7-(4'-trimethylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo [5.4.1^6,8.0]undecane

Chemical Property:

Purity/Quality:

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Technology Process of (2S,6R,7S,8S)-(1'Z)-2-(benzyloxymethyloxymethyl)-7-(4'-trimethylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo [5.4.1^6,8.0]undecane

There total 3 articles about (2S,6R,7S,8S)-(1'Z)-2-(benzyloxymethyloxymethyl)-7-(4'-trimethylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo [5.4.1^6,8.0]undecane 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: 95.0%

trimethylsilylacetylene (1066-54-2) + (2S,6R,7S,8S)-(1'Z)-2-(benzyloxymethyloxymethyl)-7-(2'-iodoethenyl)-1-aza-12-oxatricyclo[5.4.16,8.0]undecane (460710-26-3) → (2S,6R,7S,8S)-(1'Z)-2-(benzyloxymethyloxymethyl)-7-(4'-trimethylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo [5.4.16,8.0]undecane (460710-27-4)

Guidance literature:

With copper(l) iodide; diethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾;

DOI:10.1039/b111514f

Reference yield:

(2S,6R,7R, 8S)-2-(Benzyloxymethyloxymethyl)-7-cyano-1-aza-12-oxatricyclo [5.4.16,8.0]undecane (460710-25-2) → (2S,6R,7S,8S)-(1'Z)-2-(benzyloxymethyloxymethyl)-7-(4'-trimethylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo [5.4.16,8.0]undecane (460710-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / DIBALH / toluene / -78 °C

2.1: KN(TMS)2 / tetrahydrofuran / -30 °C

2.2: 82 percent / tetrahydrofuran / -78 °C

3.1: 95 percent / Et₂NH; CuI / Pd(PPh₃)4

With copper(l) iodide; potassium hexamethylsilazane; diisobutylaluminium hydride; diethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; toluene; 2.2: Stark-Wittig reaction / 3.1: Sonogashira ethynylation;

DOI:10.1039/b111514f

Reference yield:

(2S,6R,7S,8S)-2-(benzyloxymethyloxymethyl)-7-formyl-1-aza-12-oxatricyclo [5.4.16,8.0] undecane (460710-41-2) → (2S,6R,7S,8S)-(1'Z)-2-(benzyloxymethyloxymethyl)-7-(4'-trimethylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo [5.4.16,8.0]undecane (460710-27-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: KN(TMS)2 / tetrahydrofuran / -30 °C

1.2: 82 percent / tetrahydrofuran / -78 °C

2.1: 95 percent / Et₂NH; CuI / Pd(PPh₃)4

With copper(l) iodide; potassium hexamethylsilazane; diethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1.2: Stark-Wittig reaction / 2.1: Sonogashira ethynylation;

DOI:10.1039/b111514f

upstream raw materials:

trimethylsilylacetylene

(2S,6R,7S,8S)-(1'Z)-2-(benzyloxymethyloxymethyl)-7-(2'-iodoethenyl)-1-aza-12-oxatricyclo[5.4.1^6,8.0]undecane

(2S,6R,7S,8S)-2-(benzyloxymethyloxymethyl)-7-formyl-1-aza-12-oxatricyclo [5.4.1^6,8.0] undecane

(2S,6R,7R, 8S)-2-(Benzyloxymethyloxymethyl)-7-cyano-1-aza-12-oxatricyclo [5.4.1^6,8.0]undecane

Downstream raw materials:

allodihydrohistrionicotoxin

(2S,6R,7S,8S)-(1'Z)-2-(para-toluenesulfonyloxymethyl)-7-(4'-trimethylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo[5.4.1^6,8.0]undecane

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