(7R,8R,8aS)-8-Benzyloxy-8-methyl-6-[(R)-2-methyl-hex-(E)-ylidene]-7-triethylsilanyloxy-octahydro-indolizine

Base Information

Chemical Name:(7R,8R,8aS)-8-Benzyloxy-8-methyl-6-[(R)-2-methyl-hex-(E)-ylidene]-7-triethylsilanyloxy-octahydro-indolizine
CAS No.:289659-63-8
Molecular Formula:C₂₉H₄₉NO₂Si
Molecular Weight:471.799
Hs Code.:

Synonyms:(7R,8R,8aS)-8-Benzyloxy-8-methyl-6-[(R)-2-methyl-hex-(E)-ylidene]-7-triethylsilanyloxy-octahydro-indolizine

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Chemical Property of (7R,8R,8aS)-8-Benzyloxy-8-methyl-6-[(R)-2-methyl-hex-(E)-ylidene]-7-triethylsilanyloxy-octahydro-indolizine

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Technology Process of (7R,8R,8aS)-8-Benzyloxy-8-methyl-6-[(R)-2-methyl-hex-(E)-ylidene]-7-triethylsilanyloxy-octahydro-indolizine

There total 12 articles about (7R,8R,8aS)-8-Benzyloxy-8-methyl-6-[(R)-2-methyl-hex-(E)-ylidene]-7-triethylsilanyloxy-octahydro-indolizine 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%

: 617-86-7
triethylsilane

: 243454-16-2
(R)-2-Benzyloxy-2-[(S)-1-((R)-4-methyl-oct-2-ynyl)-pyrrolidin-2-yl]-propionaldehyde

: 289659-63-8
(7R,8R,8aS)-8-Benzyloxy-8-methyl-6-[(R)-2-methyl-hex-(E)-ylidene]-7-triethylsilanyloxy-octahydro-indolizine

Guidance literature:: With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; tributylphosphine; In tetrahydrofuran; at 0 ℃; for 18h;
DOI:10.1021/ja990997+

Reference yield:

: 243454-15-1
(R)-2-Benzyloxy-2-[(S)-1-((R)-4-methyl-oct-2-ynyl)-pyrrolidin-2-yl]-propan-1-ol

: 289659-63-8
(7R,8R,8aS)-8-Benzyloxy-8-methyl-6-[(R)-2-methyl-hex-(E)-ylidene]-7-triethylsilanyloxy-octahydro-indolizine

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / (COCl)2; DMSO; Et₃N

2: 95 percent / Ni(COD)2; PBu₃ / tetrahydrofuran / 0 °C

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; oxalyl dichloride; tributylphosphine; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1: Swern oxidation / 2: Cyclization;
DOI:10.1021/ja001440t

Reference yield:

: 123190-88-5
(R)-2-(S)-Pyrrolidin-2-yl-1-(2-trimethylsilanyl-ethoxymethoxy)-propan-2-ol

: 289659-63-8
(7R,8R,8aS)-8-Benzyloxy-8-methyl-6-[(R)-2-methyl-hex-(E)-ylidene]-7-triethylsilanyloxy-octahydro-indolizine

Guidance literature:: Multi-step reaction with 5 steps

1: i-Pr₂NEt / tetrahydrofuran

2: 83 percent / KH / tetrahydrofuran

3: 94 percent / NBu₄F / tetrahydrofuran

4: 93 percent / (COCl)2; DMSO; Et₃N

5: 95 percent / Ni(COD)2; PBu₃ / tetrahydrofuran / 0 °C

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; oxalyl dichloride; tributylphosphine; tetrabutyl ammonium fluoride; potassium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1: propargylation / 2: benzylation / 3: deacetalization / 4: Swern oxidation / 5: Cyclization;
DOI:10.1021/ja001440t