(2R,2''R,4R,6R)-6-(2''-Benzyloxy-4''-pentenyl)-4-(methoxycarbonylmethyl)-2-phenyl-1,3-dioxane

Base Information

Chemical Name:(2R,2''R,4R,6R)-6-(2''-Benzyloxy-4''-pentenyl)-4-(methoxycarbonylmethyl)-2-phenyl-1,3-dioxane
CAS No.:201419-22-9
Molecular Formula:C₂₅H₃₀O₅
Molecular Weight:410.51
Hs Code.:

Synonyms:(2R,2''R,4R,6R)-6-(2''-Benzyloxy-4''-pentenyl)-4-(methoxycarbonylmethyl)-2-phenyl-1,3-dioxane

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Chemical Property of (2R,2''R,4R,6R)-6-(2''-Benzyloxy-4''-pentenyl)-4-(methoxycarbonylmethyl)-2-phenyl-1,3-dioxane

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Technology Process of (2R,2''R,4R,6R)-6-(2''-Benzyloxy-4''-pentenyl)-4-(methoxycarbonylmethyl)-2-phenyl-1,3-dioxane

There total 8 articles about (2R,2''R,4R,6R)-6-(2''-Benzyloxy-4''-pentenyl)-4-(methoxycarbonylmethyl)-2-phenyl-1,3-dioxane 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: 72.0%

: 100-52-7
benzaldehyde

: 201419-21-8
Methyl (2E,5S,7R)-7-benzyloxy-5-hydroxy-2,9-decanedienoate

: 201419-22-9
(2R,2''R,4R,6R)-6-(2''-Benzyloxy-4''-pentenyl)-4-(methoxycarbonylmethyl)-2-phenyl-1,3-dioxane

Guidance literature:: With potassium tert-butylate; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0040-4039(97)10455-5

Reference yield:

: 201419-20-7
Methyl (2E,5S,7R)-7-benzyloxy-5-dimethylphenylsilyl-2,9-decanedienoate

: 201419-22-9
(2R,2''R,4R,6R)-6-(2''-Benzyloxy-4''-pentenyl)-4-(methoxycarbonylmethyl)-2-phenyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 2 steps

1.1: BF₃*2AcOH / CH₂Cl₂ / 0.08 h / 20 °C

1.2: 72 percent / KF; MCPBA / dimethylformamide / 2 h / 0 °C

2.1: 72 percent / t-BuOK / tetrahydrofuran / 0.25 h / 0 °C

With potassium tert-butylate; boron trifluoride diacetate; In tetrahydrofuran; dichloromethane; 1.1: Fluorination / 1.2: Oxidation / 2.1: Cyclization;
DOI:10.1002/(SICI)1521-3765(19991001)5:10<2850::AID-CHEM2850>3.0.CO;2-7

Reference yield:

: 251908-42-6
(2'E,4S,5'S)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-7'-oxo-2'-heptenoyl]-oxazolidin-2-one

: 201419-22-9
(2R,2''R,4R,6R)-6-(2''-Benzyloxy-4''-pentenyl)-4-(methoxycarbonylmethyl)-2-phenyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 5 steps

1.1: B-methoxy-bis(4-isocaranyl)borane / tetrahydrofuran; diethyl ether / 1.25 h / -78 - 20 °C

1.2: tetrahydrofuran; diethyl ether / 1 h / -78 °C

1.3: H₂O₂; H₂O / tetrahydrofuran; diethyl ether; methanol / 15 h / Heating

2.1: 83 percent / CF₃SO₃H / CH₂Cl₂; hexane / 15 h / 20 °C

3.1: 88 percent / methanol; tetrahydrofuran; CH₂Cl₂ / 0.08 h / 0 °C

4.1: BF₃*2AcOH / CH₂Cl₂ / 0.08 h / 20 °C

4.2: 72 percent / KF; MCPBA / dimethylformamide / 2 h / 0 °C

5.1: 72 percent / t-BuOK / tetrahydrofuran / 0.25 h / 0 °C

With trifluorormethanesulfonic acid; B-methoxy-bis(2-isocaranyl)borane; potassium tert-butylate; boron trifluoride diacetate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; 1.1: Substitution / 1.2: Addition / 1.3: Hydrolysis / 2.1: Etherification / 3.1: Ring cleavage / 4.1: Fluorination / 4.2: Oxidation / 5.1: Cyclization;
DOI:10.1002/(SICI)1521-3765(19991001)5:10<2850::AID-CHEM2850>3.0.CO;2-7