(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

Base Information

• Chemical Name: (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
• CAS No.: 1414934-31-8
• Molecular Formula: C₂₅H₃₅NO₄SSi
• Molecular Weight: 473.709

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (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

There total 5 articles about (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 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: 53.0%

toluene-4-sulfonic acid (104-15-4) + (2S,6R,7S,8S)-(1'Z)-2-(hydroxymethyl)-7-(4'-trimethylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo[5.4.16,8.0]undecane (460710-33-2) → (2S,6R,7S,8S)-(1'Z)-2-(para-toluenesulfonyloxymethyl)-7-(4'-trimethylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo[5.4.16,8.0]undecane (1414934-31-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 25 ℃; for 3h;

DOI:10.1039/c2ob26333e DOI:10.1039/c2ob26333e

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-(para-toluenesulfonyloxymethyl)-7-(4'-trimethylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo[5.4.16,8.0]undecane (1414934-31-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / toluene / 0.75 h / -78 °C / Inert atmosphere

2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -30 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

3.1: copper(l) iodide; diethylamine / 0.25 h / Inert atmosphere; Darkness

3.2: 1 h / 25 °C / Inert atmosphere

4.1: Amberlyst-15? resin / methanol / 25 °C

4.2: 1 h

5.1: dmap; triethylamine / dichloromethane / 3 h / 25 °C

With dmap; copper(l) iodide; potassium hexamethylsilazane; diisobutylaluminium hydride; diethylamine; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; 3.1: |Sonogashira Cross-Coupling / 3.2: |Sonogashira Cross-Coupling;

DOI:10.1039/c2ob26333e DOI:10.1039/c2ob26333e

Reference yield:

(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) → (2S,6R,7S,8S)-(1'Z)-2-(para-toluenesulfonyloxymethyl)-7-(4'-trimethylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo[5.4.16,8.0]undecane (1414934-31-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Amberlyst-15? resin / methanol / 25 °C

1.2: 1 h

2.1: dmap; triethylamine / dichloromethane / 3 h / 25 °C

With dmap; triethylamine; In methanol; dichloromethane;

DOI:10.1039/c2ob26333e DOI:10.1039/c2ob26333e

upstream raw materials:

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

(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

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