(3S,4R)-(E)-3-benzoyloxy-7-benzyloxy-4-methoxymethoxymethylhept-5-en-1-yne

Base Information

Chemical Name:(3S,4R)-(E)-3-benzoyloxy-7-benzyloxy-4-methoxymethoxymethylhept-5-en-1-yne
CAS No.:141859-07-6
Molecular Formula:C₂₄H₂₆O₅
Molecular Weight:394.467
Hs Code.:

Synonyms:(3S,4R)-(E)-3-benzoyloxy-7-benzyloxy-4-methoxymethoxymethylhept-5-en-1-yne

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4R)-(E)-3-benzoyloxy-7-benzyloxy-4-methoxymethoxymethylhept-5-en-1-yne

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Technology Process of (3S,4R)-(E)-3-benzoyloxy-7-benzyloxy-4-methoxymethoxymethylhept-5-en-1-yne

There total 9 articles about (3S,4R)-(E)-3-benzoyloxy-7-benzyloxy-4-methoxymethoxymethylhept-5-en-1-yne 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%

: 103-82-2
phenylacetic acid

: 141859-05-4
(3R,4R)-(E)-7-benzyloxy-4-methoxymethoxymethylhept-5-en-1-yn-3-ol

: 141859-07-6
(3S,4R)-(E)-3-benzoyloxy-7-benzyloxy-4-methoxymethoxymethylhept-5-en-1-yne

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 0.166667h;
DOI:10.3987/COM-91-S79

Reference yield:

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

: 141859-07-6
(3S,4R)-(E)-3-benzoyloxy-7-benzyloxy-4-methoxymethoxymethylhept-5-en-1-yne

Guidance literature:: Multi-step reaction with 9 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

8: tetra-n-butylammonium fluoride / tetrahydrofuran / 0.08 h / Ambient temperature

9: 84 percent / PPh₃, diisopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / 0 °C

With potassium fluoride on basic alumina; n-butyllithium; di-isopropyl azodicarboxylate; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 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

: 141859-07-6
(3S,4R)-(E)-3-benzoyloxy-7-benzyloxy-4-methoxymethoxymethylhept-5-en-1-yne

Guidance literature:: Multi-step reaction with 8 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

7: tetra-n-butylammonium fluoride / tetrahydrofuran / 0.08 h / Ambient temperature

8: 84 percent / PPh₃, diisopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / 0 °C

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