(4S,5R)-1,5-bis(tert-butyldimethylsilyloxy)-6-(p-methoxybenzyloxy)-4-methyl-2-hexyne

Base Information

Chemical Name:(4S,5R)-1,5-bis(tert-butyldimethylsilyloxy)-6-(p-methoxybenzyloxy)-4-methyl-2-hexyne
CAS No.:613257-86-6
Molecular Formula:C₂₇H₄₈O₄Si₂
Molecular Weight:492.847
Hs Code.:

Synonyms:(4S,5R)-1,5-bis(tert-butyldimethylsilyloxy)-6-(p-methoxybenzyloxy)-4-methyl-2-hexyne

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Chemical Property of (4S,5R)-1,5-bis(tert-butyldimethylsilyloxy)-6-(p-methoxybenzyloxy)-4-methyl-2-hexyne

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Technology Process of (4S,5R)-1,5-bis(tert-butyldimethylsilyloxy)-6-(p-methoxybenzyloxy)-4-methyl-2-hexyne

There total 3 articles about (4S,5R)-1,5-bis(tert-butyldimethylsilyloxy)-6-(p-methoxybenzyloxy)-4-methyl-2-hexyne 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:

: 69739-34-0
t-butyldimethylsiyl triflate

: 873924-32-4
(4S,5R)-6-(4-methoxybenzyloxy)-4-methyl-2-hexyne-1,5-diol

: 613257-86-6
(4S,5R)-1,5-bis(tert-butyldimethylsilyloxy)-6-(p-methoxybenzyloxy)-4-methyl-2-hexyne

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃; for 1.5h;
DOI:10.1021/jo0348930

Reference yield:

: 613257-85-5
(2R,3S)-1-(p-methoxybenzyloxy)-3-methyl-4-pentyn-2-ol

: 613257-86-6
(4S,5R)-1,5-bis(tert-butyldimethylsilyloxy)-6-(p-methoxybenzyloxy)-4-methyl-2-hexyne

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

1.2: tetrahydrofuran; hexane / 18 h / -78 - 20 °C

2.1: 186 mg / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

With 2,6-dimethylpyridine; n-butyllithium; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo0348930

Reference yield:

: (4S)-5-hydroxy-6-(4-methoxybenzyloxy)-4-methyl-2-hexynyl-2,2-dimethylpropionate

: 613257-86-6
(4S,5R)-1,5-bis(tert-butyldimethylsilyloxy)-6-(p-methoxybenzyloxy)-4-methyl-2-hexyne

Guidance literature:: Multi-step reaction with 2 steps

1: DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

2: 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; In dichloromethane;
DOI:10.1016/j.bmcl.2005.09.084