(1R)-1-{(2R)-4-oxo-6-[(E)-2-phenyl-1-ethenyl]-3,4-dihydro-2H-2-pyranylmethyl}-3-butenyl acrylate

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Chemical Name:(1R)-1-{(2R)-4-oxo-6-[(E)-2-phenyl-1-ethenyl]-3,4-dihydro-2H-2-pyranylmethyl}-3-butenyl acrylate
CAS No.:885322-76-9
Molecular Formula:C₂₁H₂₂O₄
Molecular Weight:338.403
Hs Code.:

Synonyms:(1R)-1-{(2R)-4-oxo-6-[(E)-2-phenyl-1-ethenyl]-3,4-dihydro-2H-2-pyranylmethyl}-3-butenyl acrylate

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Chemical Property of (1R)-1-{(2R)-4-oxo-6-[(E)-2-phenyl-1-ethenyl]-3,4-dihydro-2H-2-pyranylmethyl}-3-butenyl acrylate

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Technology Process of (1R)-1-{(2R)-4-oxo-6-[(E)-2-phenyl-1-ethenyl]-3,4-dihydro-2H-2-pyranylmethyl}-3-butenyl acrylate

There total 9 articles about (1R)-1-{(2R)-4-oxo-6-[(E)-2-phenyl-1-ethenyl]-3,4-dihydro-2H-2-pyranylmethyl}-3-butenyl acrylate 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: 89.0%

: 885322-75-8
(1R,3R,8E)-1-allyl-3-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-5,7-dioxo-9-phenyl-8-nonenyl acrylate

: 885322-76-9
(1R)-1-{(2R)-4-oxo-6-[(E)-2-phenyl-1-ethenyl]-3,4-dihydro-2H-2-pyranylmethyl}-3-butenyl acrylate

Guidance literature:: With hydrogen fluoride; In water; acetonitrile; at 45 ℃; for 3h;
DOI:10.1021/jo060028e

Reference yield:

: 885322-69-0
(3S)-3-[(tert-butyldiphenylsilyl)oxy]-5-[(tert-butyldimethylsilyl)oxy]hexanal

: 885322-76-9
(1R)-1-{(2R)-4-oxo-6-[(E)-2-phenyl-1-ethenyl]-3,4-dihydro-2H-2-pyranylmethyl}-3-butenyl acrylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: (+)-Ipc₂BOMe / diethyl ether / 0 - 20 °C

1.2: diethyl ether / 4 h / -100 °C

1.3: NaOH; H₂O₂ / diethyl ether; H₂O / 20 °C

2.1: 94 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

3.1: 89 percent / TsOH*2H₂O / tetrahydrofuran; H₂O / 7 h / 20 °C

4.1: 88 percent / Et₃N; oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

5.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C

5.2: 63 percent / tetrahydrofuran; hexane / 0.75 h / -78 °C

6.1: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

7.1: 89 percent / HF / H₂O; acetonitrile / 3 h / 45 °C

With oxalyl dichloride; hydrogen fluoride; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; (+)-B-methoxydiisocamphenylborane; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetonitrile; 1.2: Brown asymmetric alkylation / 4.1: Swern oxidation;
DOI:10.1021/jo060028e

Reference yield:

: 885322-68-9
(3R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]hex-5-ene

: 885322-76-9
(1R)-1-{(2R)-4-oxo-6-[(E)-2-phenyl-1-ethenyl]-3,4-dihydro-2H-2-pyranylmethyl}-3-butenyl acrylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: N-methylmorpholine N-oxide; OsO₄ / tetrahydrofuran; H₂O / 10 h / 20 °C

1.2: 84 percent / NaIO₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

2.1: (+)-Ipc₂BOMe / diethyl ether / 0 - 20 °C

2.2: diethyl ether / 4 h / -100 °C

2.3: NaOH; H₂O₂ / diethyl ether; H₂O / 20 °C

3.1: 94 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

4.1: 89 percent / TsOH*2H₂O / tetrahydrofuran; H₂O / 7 h / 20 °C

5.1: 88 percent / Et₃N; oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

6.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C

6.2: 63 percent / tetrahydrofuran; hexane / 0.75 h / -78 °C

7.1: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

8.1: 89 percent / HF / H₂O; acetonitrile / 3 h / 45 °C

With osmium(VIII) oxide; oxalyl dichloride; hydrogen fluoride; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; (+)-B-methoxydiisocamphenylborane; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetonitrile; 2.2: Brown asymmetric alkylation / 5.1: Swern oxidation;
DOI:10.1021/jo060028e