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

Base Information

Chemical Name:(S)-hept-6-en-2-yl (3R,4S,5S)-5-benzyloxy-4-hydroxy-3-methoxyhept-6-enoate
CAS No.:917096-35-6
Molecular Formula:C₂₂H₃₂O₅
Molecular Weight:376.493
Hs Code.:

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

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

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

There total 16 articles about (S)-hept-6-en-2-yl (3R,4S,5S)-5-benzyloxy-4-hydroxy-3-methoxyhept-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: 93.0%

: 917096-34-5
(S)-hept-6-en-2-yl (3R,4S,5S)-5-benzyloxy-3-methoxy-4-(4-methoxybenzyloxy)hept-6-enoate

: 917096-35-6
(S)-hept-6-en-2-yl (3R,4S,5S)-5-benzyloxy-4-hydroxy-3-methoxyhept-6-enoate

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; for 2h;
DOI:10.1016/j.tetlet.2006.09.145

Reference yield:

: 917096-32-3
methyl (3R,4S,5S)-5-benzyloxy-3-methoxy-4-(4-methoxybenzyloxy)hept-6-enoate

: 917096-35-6
(S)-hept-6-en-2-yl (3R,4S,5S)-5-benzyloxy-4-hydroxy-3-methoxyhept-6-enoate

Guidance literature:: Multi-step reaction with 4 steps

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

2: Et₃N / tetrahydrofuran / 1 h / 20 °C

3: 196 mg / DMAP / tetrahydrofuran / 18 h / 20 °C

4: 93 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

With dmap; lithium hydroxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; 2: Yamaguchi esterification / 3: Yamaguchi esterification;
DOI:10.1016/j.carres.2007.04.013

Reference yield:

: 917096-25-4
(3R,4S,5S)-5-benzyloxy-3-methoxy-4-(4-methoxybenzyloxy)hept-6-enoic acid

: 917096-35-6
(S)-hept-6-en-2-yl (3R,4S,5S)-5-benzyloxy-4-hydroxy-3-methoxyhept-6-enoate

Guidance literature:: Multi-step reaction with 3 steps

1: Et₃N / tetrahydrofuran / 1 h / 20 °C

2: 196 mg / DMAP / tetrahydrofuran / 18 h / 20 °C

3: 93 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

With dmap; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; 1: Yamaguchi esterification / 2: Yamaguchi esterification;
DOI:10.1016/j.carres.2007.04.013