p-toluenesulfonic acid (2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptyl ester

Base Information

Chemical Name:p-toluenesulfonic acid (2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptyl ester
CAS No.:398477-94-6
Molecular Formula:C₃₇H₆₀O₇SSi₂
Molecular Weight:705.116
Hs Code.:

Synonyms:p-toluenesulfonic acid (2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptyl ester

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Chemical Property of p-toluenesulfonic acid (2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptyl ester

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Technology Process of p-toluenesulfonic acid (2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptyl ester

There total 8 articles about p-toluenesulfonic acid (2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptyl ester 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: 91.0%

: 98-59-9
p-toluenesulfonyl chloride

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

: 398477-94-6
p-toluenesulfonic acid (2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1021/ja0177713

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 398477-94-6
p-toluenesulfonic acid (2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptyl ester

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 91 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

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

Reference yield:

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

: 398477-94-6
p-toluenesulfonic acid (2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptyl ester

Guidance literature:: Multi-step reaction with 7 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

7.1: 91 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

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