(2R,4aS,5S,8aR)-1-benzyl-2-(2-benzyloxy)ethyl-4-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-1,2,4a,5,6,7,8,8a-octahydroquinoline

Base Information

Chemical Name:(2R,4aS,5S,8aR)-1-benzyl-2-(2-benzyloxy)ethyl-4-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-1,2,4a,5,6,7,8,8a-octahydroquinoline
CAS No.:1007401-54-8
Molecular Formula:C₃₃H₄₉NO₄Si
Molecular Weight:551.842
Hs Code.:

Synonyms:(2R,4aS,5S,8aR)-1-benzyl-2-(2-benzyloxy)ethyl-4-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-1,2,4a,5,6,7,8,8a-octahydroquinoline

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Chemical Property of (2R,4aS,5S,8aR)-1-benzyl-2-(2-benzyloxy)ethyl-4-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-1,2,4a,5,6,7,8,8a-octahydroquinoline

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Technology Process of (2R,4aS,5S,8aR)-1-benzyl-2-(2-benzyloxy)ethyl-4-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-1,2,4a,5,6,7,8,8a-octahydroquinoline

There total 15 articles about (2R,4aS,5S,8aR)-1-benzyl-2-(2-benzyloxy)ethyl-4-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-1,2,4a,5,6,7,8,8a-octahydroquinoline 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:

: 176907-55-4
trans-7-(t-butyldiphenylsilyloxy)hept-2-en-1-ol

: 1007401-54-8
(2R,4aS,5S,8aR)-1-benzyl-2-(2-benzyloxy)ethyl-4-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-1,2,4a,5,6,7,8,8a-octahydroquinoline

Guidance literature:: Multi-step reaction with 15 steps

1.1: 90 percent / molecular sieves 4 Angtroem; Ti(Oi-Pr)4; t-BuOOH / (+)-diethyl tartrate / CH₂Cl₂; benzene / -20 °C

2.1: 95 percent / Red-Al / tetrahydrofuran / 0 - 20 °C

3.1: 88 percent / pyridine / 0 - 20 °C

4.1: 82 percent / i-Pr₂NEt / 2 h / 0 - 20 °C

5.1: 100 percent / DIBAL-H / diethyl ether; hexane / 2 h / -60 °C

6.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: 88 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

8.1: 80 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

9.1: 87 percent / TBAF / tetrahydrofuran / 0 - 20 °C

10.1: 81 percent / MnO₂; O₂ / CH₂Cl₂ / 12 h / 20 °C

11.1: 99 percent / pyridine / 20 °C

12.1: 62 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

13.1: 76 percent / DIBAL / diethyl ether; hexane / 0.25 h / -70 °C

14.1: triethylamine; DMSO; SO₃*Py / CH₂Cl₂ / 0 - 20 °C

15.1: anhydrous magnesium sulfate / diethyl ether / 0.5 h / 0 °C

15.2: indium triflate / acetonitrile / 12 h / 0 - 20 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; manganese(IV) oxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; pyridine-SO₃ complex; 4 A molecular sieve; tetrabutyl ammonium fluoride; oxygen; diisobutylaluminium hydride; magnesium sulfate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; (+)-Weinsaeure-diethylester; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene; 1.1: Katsuki-Sharpless asymmetric epoxidation / 15.2: Diels-Alder reaction;
DOI:10.3390/12020194

Reference yield:

: 1007401-53-7
(S,6Z,8E)-11-benzyloxy-7-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)undeca-6,8-dienal

: 100-46-9
benzylamine

: (2S,4aR,5S,8aR)-1-benzyl-2-(2-benzyloxy)ethyl-4-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-1,2,4a,5,6,7,8,8a-octahydroquinoline

: 1007401-54-8
(2R,4aS,5S,8aR)-1-benzyl-2-(2-benzyloxy)ethyl-4-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-1,2,4a,5,6,7,8,8a-octahydroquinoline

Guidance literature:: (S,6Z,8E)-11-benzyloxy-7-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)undeca-6,8-dienal; benzylamine; With magnesium sulfate; In diethyl ether; at 0 ℃; for 0.5h;

With indium(III) triflate; In acetonitrile; at 0 - 20 ℃; for 12h;
DOI:10.3390/12020194

Reference yield:

: 1007401-51-5
(S,E)-1-benzyloxy-11-hydroxy-7-(methoxymethoxy)undec-3-en-5-one

: 1007401-54-8
(2R,4aS,5S,8aR)-1-benzyl-2-(2-benzyloxy)ethyl-4-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-1,2,4a,5,6,7,8,8a-octahydroquinoline

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / pyridine / 20 °C

2.1: 62 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

3.1: 76 percent / DIBAL / diethyl ether; hexane / 0.25 h / -70 °C

4.1: triethylamine; DMSO; SO₃*Py / CH₂Cl₂ / 0 - 20 °C

5.1: anhydrous magnesium sulfate / diethyl ether / 0.5 h / 0 °C

5.2: indium triflate / acetonitrile / 12 h / 0 - 20 °C

With pyridine; pyridine-SO₃ complex; diisobutylaluminium hydride; magnesium sulfate; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 5.2: Diels-Alder reaction;
DOI:10.3390/12020194