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

Base Information

• Chemical Name: (2S,6R,7S,8S)-2-(benzyloxymethyloxymethyl)-7-formyl-1-aza-12-oxatricyclo [5.4.1^6,8.0] undecane
• CAS No.: 460710-41-2
• Molecular Formula: C₂₀H₂₇NO₄
• Molecular Weight: 345.439

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

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

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

There total 1 articles about (2S,6R,7S,8S)-2-(benzyloxymethyloxymethyl)-7-formyl-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: 100.0%

(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)-2-(benzyloxymethyloxymethyl)-7-formyl-1-aza-12-oxatricyclo [5.4.16,8.0] undecane (460710-41-2)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃;

DOI:10.1039/b111514f

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,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'-triisopropylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxatricyclo [5.4.16,8.0]undecane (460710-28-5)

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: 100 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:

(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-(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

(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-(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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