methyl (4R,5S)-(E)-8-benzyloxy-4-tert-butyldimethylsilyloxy-5-methyl-oct-6-en-2-ynoate

Base Information

Chemical Name:methyl (4R,5S)-(E)-8-benzyloxy-4-tert-butyldimethylsilyloxy-5-methyl-oct-6-en-2-ynoate
CAS No.:121896-40-0
Molecular Formula:C₂₃H₃₄O₄Si
Molecular Weight:402.606
Hs Code.:

Synonyms:methyl (4R,5S)-(E)-8-benzyloxy-4-tert-butyldimethylsilyloxy-5-methyl-oct-6-en-2-ynoate

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Chemical Property of methyl (4R,5S)-(E)-8-benzyloxy-4-tert-butyldimethylsilyloxy-5-methyl-oct-6-en-2-ynoate

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Technology Process of methyl (4R,5S)-(E)-8-benzyloxy-4-tert-butyldimethylsilyloxy-5-methyl-oct-6-en-2-ynoate

There total 8 articles about methyl (4R,5S)-(E)-8-benzyloxy-4-tert-butyldimethylsilyloxy-5-methyl-oct-6-en-2-ynoate 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:

: 131101-47-8,135501-85-8,110339-27-0
(R)-5-Benzyloxy-4-hydroxy-2-pentyne

: 121896-40-0
methyl (4R,5S)-(E)-8-benzyloxy-4-tert-butyldimethylsilyloxy-5-methyl-oct-6-en-2-ynoate

Guidance literature:: Multi-step reaction with 6 steps

1: H₂ / Lindlar catalyst / ethyl acetate / Ambient temperature

2: 1.) KF-Al₂O₃; 2.) EtMgBr / 1.) CH₃CN, rt; 2.) Et₂O, 0 deg C

3: 90 percent / n-BuLi / tetrahydrofuran / -78 °C

4: n-Bu₄NF / tetrahydrofuran / Ambient temperature

5: 87 percent / imidazole / dimethylformamide / Ambient temperature

6: 1.)n-BuLi / 1.) THF, -72 deg C; 2.) THF, -45 deg C

With 1H-imidazole; potassium fluoride on basic alumina; n-butyllithium; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; Lindlar's catalyst; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1246/cl.1988.2041

Reference yield:

: 110339-29-2
(R)-(Z)-1-Benzyloxy-2-hydroxy-3-pentene

: 121896-40-0
methyl (4R,5S)-(E)-8-benzyloxy-4-tert-butyldimethylsilyloxy-5-methyl-oct-6-en-2-ynoate

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) KF-Al₂O₃; 2.) EtMgBr / 1.) CH₃CN, rt; 2.) Et₂O, 0 deg C

2: 90 percent / n-BuLi / tetrahydrofuran / -78 °C

3: n-Bu₄NF / tetrahydrofuran / Ambient temperature

4: 87 percent / imidazole / dimethylformamide / Ambient temperature

5: 1.)n-BuLi / 1.) THF, -72 deg C; 2.) THF, -45 deg C

With 1H-imidazole; potassium fluoride on basic alumina; n-butyllithium; ethylmagnesium bromide; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1246/cl.1988.2041

Reference yield:

: 120448-41-1
(3R,4S)-(E)-7-benzyloxy-4-methylhept-5-en-1-yn-3-ol

: 121896-40-0
methyl (4R,5S)-(E)-8-benzyloxy-4-tert-butyldimethylsilyloxy-5-methyl-oct-6-en-2-ynoate

Guidance literature:: Multi-step reaction with 2 steps

1: 87 percent / imidazole / dimethylformamide / Ambient temperature

2: 1.)n-BuLi / 1.) THF, -72 deg C; 2.) THF, -45 deg C

With 1H-imidazole; n-butyllithium; In N,N-dimethyl-formamide;
DOI:10.1246/cl.1988.2041