(S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-hydroxyhept-6-enoate

Base Information

Chemical Name:(S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-hydroxyhept-6-enoate
CAS No.:916154-12-6
Molecular Formula:C₂₈H₃₄O₆
Molecular Weight:466.574
Hs Code.:

Synonyms:(S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-hydroxyhept-6-enoate

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Chemical Property of (S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-hydroxyhept-6-enoate

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Technology Process of (S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-hydroxyhept-6-enoate

There total 11 articles about (S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-hydroxyhept-6-enoate 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: 90.0%

: 916154-11-5
(S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-(p-methoxybenzyloxy)hept-6-enoate

: 916154-12-6
(S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-hydroxyhept-6-enoate

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 2h;
DOI:10.1021/jo0615504

Reference yield:

: 916154-05-7
(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran

: 916154-12-6
(S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-hydroxyhept-6-enoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 74 percent / pyridinium chlorochromate; silica gel / CH₂Cl₂ / 6 h / 45 °C

2.1: 83 percent / methanol / 3 h / 20 °C / pH 9 - 10

3.1: 75 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 3 h

4.1: LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 12 h / 20 °C

5.1: triethylamine / tetrahydrofuran / 1 h / 20 °C

5.2: 400 mg / DMAP / tetrahydrofuran / 18 h / 20 °C

6.1: 83 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4.5 h / 0 - 20 °C

7.1: 95 percent / pyridine; DMAP / 3 h / 20 °C

8.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 2 h / 20 °C

With pyridine; dmap; lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; silica gel; triethylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jo0615504

Reference yield:

: 916154-04-6
((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol

: 916154-12-6
(S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-hydroxyhept-6-enoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / 0.5 h / 20 °C

1.2: 75 percent / n-BuLi / CH₂Cl₂; hexane; tetrahydrofuran / 2 h / 20 °C

2.1: 74 percent / pyridinium chlorochromate; silica gel / CH₂Cl₂ / 6 h / 45 °C

3.1: 83 percent / methanol / 3 h / 20 °C / pH 9 - 10

4.1: 75 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 3 h

5.1: LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 12 h / 20 °C

6.1: triethylamine / tetrahydrofuran / 1 h / 20 °C

6.2: 400 mg / DMAP / tetrahydrofuran / 18 h / 20 °C

7.1: 83 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4.5 h / 0 - 20 °C

8.1: 95 percent / pyridine; DMAP / 3 h / 20 °C

9.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 2 h / 20 °C

With pyridine; dmap; lithium hydroxide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; silica gel; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: Swern oxidation / 1.2: Wittig reaction;
DOI:10.1021/jo0615504