(2S,3R,5R)-3-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-ynal

Base Information

Chemical Name:(2S,3R,5R)-3-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-ynal
CAS No.:896730-06-6
Molecular Formula:C₂₆H₄₄O₄Si₂
Molecular Weight:476.804
Hs Code.:

Synonyms:(2S,3R,5R)-3-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-ynal

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Chemical Property of (2S,3R,5R)-3-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-ynal

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Technology Process of (2S,3R,5R)-3-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-ynal

There total 9 articles about (2S,3R,5R)-3-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-ynal 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%

: 918310-76-6
(2S,3R,5R)-3-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-yn-1-ol

: 896730-06-6
(2S,3R,5R)-3-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-ynal

Guidance literature:: With pyridine-SO₃ complex; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; at 0 ℃; for 0.75h;
DOI:10.1021/ja066971h

Reference yield:

: 882005-23-4
(2R)-2-methyl-5-trimethylsilanyl-4-pentyn-1-ol

: 896730-06-6
(2S,3R,5R)-3-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-ynal

Guidance literature:: Multi-step reaction with 7 steps

1.1: 89 percent / imidazole; triphenyl phosphine; I₂ / CH₂Cl₂ / 3.5 h

2.1: tert-butyllithium / pentane; diethyl ether / 0.08 h / -78 °C

2.2: 90 percent / pentane; diethyl ether / 1 h

3.1: 70 percent / diisopropylethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 1.5 h / 0 °C

4.1: LiI / diethyl ether / 0.08 h / -40 °C

4.2: LiAlH₄ / diethyl ether / 2 h / -100 °C

5.1: 96 percent / imidazole; DMAP / CH₂Cl₂ / 12 h

6.1: 69 percent / pyridine; HF*pyridine / tetrahydrofuran / 3.5 h / 20 °C

7.1: 100 percent / diisopropylethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.75 h / 0 °C

With pyridine; 1H-imidazole; dmap; pyridine-SO₃ complex; iodine; tert.-butyl lithium; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; pentane;
DOI:10.1021/ja066971h

Reference yield:

: 918310-74-4
(R)-1-iodo-2-methyl-5-(trimethyl)silyl-4-pentyne

: 896730-06-6
(2S,3R,5R)-3-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-ynal

Guidance literature:: Multi-step reaction with 6 steps

1.1: tert-butyllithium / pentane; diethyl ether / 0.08 h / -78 °C

1.2: 90 percent / pentane; diethyl ether / 1 h

2.1: 70 percent / diisopropylethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 1.5 h / 0 °C

3.1: LiI / diethyl ether / 0.08 h / -40 °C

3.2: LiAlH₄ / diethyl ether / 2 h / -100 °C

4.1: 96 percent / imidazole; DMAP / CH₂Cl₂ / 12 h

5.1: 69 percent / pyridine; HF*pyridine / tetrahydrofuran / 3.5 h / 20 °C

6.1: 100 percent / diisopropylethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.75 h / 0 °C

With pyridine; 1H-imidazole; dmap; pyridine-SO₃ complex; tert.-butyl lithium; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; lithium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; pentane;
DOI:10.1021/ja066971h