(2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptan-1-ol

Base Information

Chemical Name:(2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptan-1-ol
CAS No.:398477-93-5
Molecular Formula:C₃₀H₅₄O₅Si₂
Molecular Weight:550.927
Hs Code.:

Synonyms:(2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptan-1-ol

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Chemical Property of (2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptan-1-ol

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Technology Process of (2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptan-1-ol

There total 7 articles about (2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptan-1-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: 84.0%

: 398477-92-4
(2R)-N-[(2R,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-2-(prop-2-ynyl)heptanoyl]bornane-10,2-sultam

: 398477-93-5
(2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptan-1-ol

Guidance literature:: With lithium triethylborohydride; In tetrahydrofuran; at -78 - -40 ℃; for 7h;
DOI:10.1021/ja0177713

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 398477-93-5
(2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptan-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -10 - 20 °C

2: 84 percent / LiEt₃BH / tetrahydrofuran / 7 h / -78 - -40 °C

With 2,6-dimethylpyridine; lithium triethylborohydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja0177713

Reference yield:

: 89922-82-7
3-(tert-butyldimethylsilanyloxy)propionaldehyde

: 398477-93-5
(2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptan-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: Et₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.5 h / -5 °C

1.2: 66 percent / CH₂Cl₂ / 1.5 h / -78 °C

2.1: 72 percent / TfOH / diethyl ether / 2 h / 20 °C

3.1: DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 1 h / -78 °C

4.2: 74 percent / CH₂Cl₂ / 2 h / -78 °C

5.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -10 - 20 °C

6.1: 84 percent / LiEt₃BH / tetrahydrofuran / 7 h / -78 - -40 °C

With 2,6-dimethylpyridine; trifluorormethanesulfonic acid; titanium tetrachloride; diisobutylaluminium hydride; lithium triethylborohydride; N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja0177713