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

Base Information

Chemical Name:(2S,5R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-yn-3-ol
CAS No.:918310-85-7
Molecular Formula:C₂₆H₄₆O₄Si₂
Molecular Weight:478.82
Hs Code.:

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

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Chemical Property of (2S,5R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-yn-3-ol

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Technology Process of (2S,5R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-yn-3-ol

There total 4 articles about (2S,5R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-yn-3-ol 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: 90.0%

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

: 180153-95-1
(2S)-3-tert-butyldimethylsilyloxy-2-(4-methoxybenzyloxy)propanal

: 918310-85-7
(2S,5R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-yn-3-ol

Guidance literature:: (R)-1-iodo-2-methyl-5-(trimethyl)silyl-4-pentyne; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.0833333h;

(2S)-3-tert-butyldimethylsilyloxy-2-(4-methoxybenzyloxy)propanal; In diethyl ether; pentane; for 1h;
DOI:10.1021/ja066971h

Reference yield:

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

: 918310-85-7
(2S,5R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-yn-3-ol

Guidance literature:: Multi-step reaction with 2 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

With 1H-imidazole; iodine; tert.-butyl lithium; triphenylphosphine; In diethyl ether; dichloromethane; pentane;
DOI:10.1021/ja066971h

Reference yield:

: 918310-84-6
(S)-4-benzyl-3-((R)-2-methyl-5-(trimethylsilyl)pent-4-ynoyl)oxazolidin-2-one

: 918310-85-7
(2S,5R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-yn-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 79 percent / LiBH₄; H₂O / diethyl ether / 0.83 h / 0 °C

2.1: 89 percent / imidazole; triphenyl phosphine; I₂ / CH₂Cl₂ / 3.5 h

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

3.2: 90 percent / pentane; diethyl ether / 1 h

With 1H-imidazole; lithium borohydride; water; iodine; tert.-butyl lithium; triphenylphosphine; In diethyl ether; dichloromethane; pentane;
DOI:10.1021/ja066971h