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

Base Information

• Chemical Name: (2S,6R,7S,8S)-(1'Z)-2-(benzyloxymethyloxymethyl)-7-(2'-iodoethenyl)-1-aza-12-oxatricyclo[5.4.1^6,8.0]undecane
• CAS No.: 460710-26-3
• Molecular Formula: C₂₁H₂₈INO₃
• Molecular Weight: 469.363

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

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

Chemical Property:

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

There total 2 articles about (2S,6R,7S,8S)-(1'Z)-2-(benzyloxymethyloxymethyl)-7-(2'-iodoethenyl)-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: 82.0%

(iodomethyl)triphenylphosphonium iodide (3020-28-8) + (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-(2'-iodoethenyl)-1-aza-12-oxatricyclo[5.4.16,8.0]undecane (460710-26-3)

Guidance literature:

(iodomethyl)triphenylphosphonium iodide; With potassium hexamethylsilazane; In tetrahydrofuran; at -30 ℃;

(2S,6R,7S,8S)-2-(benzyloxymethyloxymethyl)-7-formyl-1-aza-12-oxatricyclo [5.4.1^6,8.0] undecane; In tetrahydrofuran; at -78 ℃; Further stages.;

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-(2'-iodoethenyl)-1-aza-12-oxatricyclo[5.4.16,8.0]undecane (460710-26-3)

Guidance literature:

Multi-step reaction with 2 steps

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

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

2.2: 82 percent / tetrahydrofuran / -78 °C

With potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; toluene; 2.2: Stark-Wittig reaction;

DOI:10.1039/b111514f

Reference yield: 100.0%

tris-iso-propylsilyl acetylene (89343-06-6) + (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'-triisopropylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo [5.4.16,8.0]undecane (460710-28-5)

Guidance literature:

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

DOI:10.1039/b111514f

upstream raw materials:

(iodomethyl)triphenylphosphonium iodide

(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:

(2S,6R,7S,8S)-(1'Z)-2-(benzyloxymethyloxymethyl)-7-(4'-triisopropylsilyl-but-1'-en-3'-yn-1'-yl)-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

(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

allodihydrohistrionicotoxin

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