(E)-4-{(2R,3S)-3-[4-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-butyryloxy]-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester

Base Information

Chemical Name:(E)-4-{(2R,3S)-3-[4-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-butyryloxy]-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester
CAS No.:125878-22-0
Molecular Formula:C₃₂H₄₀O₇
Molecular Weight:536.665
Hs Code.:

Synonyms:(E)-4-{(2R,3S)-3-[4-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-butyryloxy]-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester

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Chemical Property of (E)-4-{(2R,3S)-3-[4-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-butyryloxy]-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester

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Technology Process of (E)-4-{(2R,3S)-3-[4-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-butyryloxy]-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester

There total 18 articles about (E)-4-{(2R,3S)-3-[4-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-butyryloxy]-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester 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: 87.0%

: 125877-95-4
4-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-butyric acid

: 125878-04-8
(E)-4-((2R,3S)-3-Hydroxy-tetrahydro-pyran-2-yl)-but-2-enoic acid benzyl ester

: 125878-22-0
(E)-4-{(2R,3S)-3-[4-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-butyryloxy]-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester

Guidance literature:: With dmap; camphor-10-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 25 ℃; for 4h;
DOI:10.1021/ja00164a026

Reference yield:

: 121422-51-3
(2S,3R)-3-hydroxy-2-vinyloxane

: 125878-22-0
(E)-4-{(2R,3S)-3-[4-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-butyryloxy]-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) KH / 1.) THF, 0 deg C, 10 min, 2.) 25 deg C, 3 h

2: 1.) 9-BBN, 2.) 30percent H₂O₂, 3 N NaOH / 1.) THF, 0 deg C

3: 85 percent / benzene / 3 h / 25 °C

4: 99 percent / H₂ / 5percent Pd/C / hexane / 0.5 h / 25 °C

5: 92 percent / LiOH / tetrahydrofuran; H₂O / 3 h / 45 °C

6: 87 percent / 1,3-dicyclohexylcarbodiimide (DCC), 4-(dimethylamino)pyridine (DMAP), camphorsulfonic acid (CSA) / CH₂Cl₂ / 4 h / 25 °C

With dmap; lithium hydroxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; camphor-10-sulfonic acid; hydrogen; dihydrogen peroxide; potassium hydride; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; benzene;
DOI:10.1021/ja00164a026

Reference yield:

: 125877-77-2
(2S,3R)-3-(benzyloxy)-2-vinyl-3,4,5,6-tetrahydro-2H-pyran

: 125878-22-0
(E)-4-{(2R,3S)-3-[4-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-butyryloxy]-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) 9-BBN, 2.) 30percent H₂O₂, 3 N NaOH / 1.) THF, 0 deg C

2: 85 percent / benzene / 3 h / 25 °C

3: 99 percent / H₂ / 5percent Pd/C / hexane / 0.5 h / 25 °C

4: 92 percent / LiOH / tetrahydrofuran; H₂O / 3 h / 45 °C

5: 87 percent / 1,3-dicyclohexylcarbodiimide (DCC), 4-(dimethylamino)pyridine (DMAP), camphorsulfonic acid (CSA) / CH₂Cl₂ / 4 h / 25 °C

With dmap; lithium hydroxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; camphor-10-sulfonic acid; hydrogen; dihydrogen peroxide; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; benzene;
DOI:10.1021/ja00164a026