(4aS,8S,8aS)-N-allyl-N-[2-benzenesulfonyl-6-(tert-butyldimethylsiloxy)-8a-formyl-1,2,3,4,4a,5,8,8a-octahydroisoquinolin-8-yl]chloroacetamide

Base Information

Chemical Name:(4aS,8S,8aS)-N-allyl-N-[2-benzenesulfonyl-6-(tert-butyldimethylsiloxy)-8a-formyl-1,2,3,4,4a,5,8,8a-octahydroisoquinolin-8-yl]chloroacetamide
CAS No.:929803-83-8
Molecular Formula:C₂₇H₃₉ClN₂O₅SSi
Molecular Weight:567.222
Hs Code.:

Synonyms:(4aS,8S,8aS)-N-allyl-N-[2-benzenesulfonyl-6-(tert-butyldimethylsiloxy)-8a-formyl-1,2,3,4,4a,5,8,8a-octahydroisoquinolin-8-yl]chloroacetamide

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Chemical Property of (4aS,8S,8aS)-N-allyl-N-[2-benzenesulfonyl-6-(tert-butyldimethylsiloxy)-8a-formyl-1,2,3,4,4a,5,8,8a-octahydroisoquinolin-8-yl]chloroacetamide

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Technology Process of (4aS,8S,8aS)-N-allyl-N-[2-benzenesulfonyl-6-(tert-butyldimethylsiloxy)-8a-formyl-1,2,3,4,4a,5,8,8a-octahydroisoquinolin-8-yl]chloroacetamide

There total 6 articles about (4aS,8S,8aS)-N-allyl-N-[2-benzenesulfonyl-6-(tert-butyldimethylsiloxy)-8a-formyl-1,2,3,4,4a,5,8,8a-octahydroisoquinolin-8-yl]chloroacetamide 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: 67.0%

: 929803-76-9
1-benzenesulfonyl-1,2,5,6-tetrahydropyridine-3-carboxaldehyde

: 929803-77-0
N-allyl-N-[(E)-3-(tert-butyldimethylsiloxy)-1,3-butadienyl]chloroacetamide

: 929803-83-8
(4aS,8S,8aS)-N-allyl-N-[2-benzenesulfonyl-6-(tert-butyldimethylsiloxy)-8a-formyl-1,2,3,4,4a,5,8,8a-octahydroisoquinolin-8-yl]chloroacetamide

Guidance literature:: With (1R,2R)-(-)-[1,2-cyclohexanediamino-N,N'-bis(3,5-di-tert-butylsalicylidene)]chromium(III) fluoride; In α,α,α-trifluorotoluene; at 20 ℃; for 20h; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1246/bcsj.82.1520

Reference yield:

: 929803-76-9
1-benzenesulfonyl-1,2,5,6-tetrahydropyridine-3-carboxaldehyde

: 929803-77-0
N-allyl-N-[(E)-3-(tert-butyldimethylsiloxy)-1,3-butadienyl]chloroacetamide

: (4aR,8R,8aR)-N-allyl-N-[2-benzenesulfonyl-6-(tert-butyldimethylsiloxy)-8a-formyl-1,2,3,4,4a,5,8,8a-octahydroisoquinolin-8-yl]chloroacetamide

: 929803-83-8
(4aS,8S,8aS)-N-allyl-N-[2-benzenesulfonyl-6-(tert-butyldimethylsiloxy)-8a-formyl-1,2,3,4,4a,5,8,8a-octahydroisoquinolin-8-yl]chloroacetamide

Guidance literature:: With (R,R)-Cr-salen; In various solvent(s); at 0 ℃; for 64h;
DOI:10.1016/j.tetlet.2006.12.029

Reference yield:

: 929803-75-8
methyl 1-benzenesulfonyl-1,2,5,6-tetrahydropyridine-3-carboxylate

: 929803-83-8
(4aS,8S,8aS)-N-allyl-N-[2-benzenesulfonyl-6-(tert-butyldimethylsiloxy)-8a-formyl-1,2,3,4,4a,5,8,8a-octahydroisoquinolin-8-yl]chloroacetamide

Guidance literature:: Multi-step reaction with 2 steps

1: 81 percent / DIBAL / toluene

2: (R,R)-Cr-salen complex; 4A MS / various solvent(s) / 64 h / 0 °C

With (R,R)-Cr-salen; diisobutylaluminium hydride; In toluene; 1: Swern oxidation / 2: Diels-Alder reaction;
DOI:10.1016/j.tetlet.2006.12.029