(3R,4R)-(Z)-7-benzyloxy-4-methoxymethoxymethyl-1-trimethylsilylhept-5-en-1-yn-3-ol

Base Information

Chemical Name:(3R,4R)-(Z)-7-benzyloxy-4-methoxymethoxymethyl-1-trimethylsilylhept-5-en-1-yn-3-ol
CAS No.:141859-04-3
Molecular Formula:C₂₀H₃₀O₄Si
Molecular Weight:362.541
Hs Code.:

Synonyms:(3R,4R)-(Z)-7-benzyloxy-4-methoxymethoxymethyl-1-trimethylsilylhept-5-en-1-yn-3-ol

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Chemical Property of (3R,4R)-(Z)-7-benzyloxy-4-methoxymethoxymethyl-1-trimethylsilylhept-5-en-1-yn-3-ol

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Technology Process of (3R,4R)-(Z)-7-benzyloxy-4-methoxymethoxymethyl-1-trimethylsilylhept-5-en-1-yn-3-ol

There total 7 articles about (3R,4R)-(Z)-7-benzyloxy-4-methoxymethoxymethyl-1-trimethylsilylhept-5-en-1-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: 97.0%

: 141859-03-2
(R)-(Z)-1-benzyloxy-5-methoxymethoxy-2-(3-trimethylsilylpropargyloxy)pent-3-ene

: 141859-04-3
(3R,4R)-(Z)-7-benzyloxy-4-methoxymethoxymethyl-1-trimethylsilylhept-5-en-1-yn-3-ol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -10 ℃; for 0.166667h;
DOI:10.3987/COM-91-S79

Reference yield:

: 131864-03-4
(R)-3-<(tert-butyldimethylsilyl)oxy>-4-(benzyloxy)but-1-yne

: 141859-04-3
(3R,4R)-(Z)-7-benzyloxy-4-methoxymethoxymethyl-1-trimethylsilylhept-5-en-1-yn-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) n-BuLi / 1.) THF, 0 deg C, 1 h, 2.) THF, 0 deg C, 5 h

2: 99 percent / (i-Pr)2NEt / CH₂Cl₂ / 42 h / Ambient temperature

3: 96 percent / H₂ / Lindlar catalyst / hexane / 760 Torr

4: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.2 h / Ambient temperature

5: 92 percent / KF-Al₂O₃ / tetrahydrofuran / 25 h / Ambient temperature

6: ethylmagnesium bromide / 1.) THF, 0 deg, 1.5 h, 2.) THF, 0 deg C, 30 min

7: 97 percent / n-BuLi / tetrahydrofuran / 0.17 h / -10 °C

With potassium fluoride on basic alumina; n-butyllithium; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.3987/COM-91-S79

Reference yield:

: 141858-98-2
(R)-5-benzyloxy-4-tert-butyldimethylsilyloxypent-2-yn-1-ol

: 141859-04-3
(3R,4R)-(Z)-7-benzyloxy-4-methoxymethoxymethyl-1-trimethylsilylhept-5-en-1-yn-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / (i-Pr)2NEt / CH₂Cl₂ / 42 h / Ambient temperature

2: 96 percent / H₂ / Lindlar catalyst / hexane / 760 Torr

3: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.2 h / Ambient temperature

4: 92 percent / KF-Al₂O₃ / tetrahydrofuran / 25 h / Ambient temperature

5: ethylmagnesium bromide / 1.) THF, 0 deg, 1.5 h, 2.) THF, 0 deg C, 30 min

6: 97 percent / n-BuLi / tetrahydrofuran / 0.17 h / -10 °C

With potassium fluoride on basic alumina; n-butyllithium; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.3987/COM-91-S79