methyl (2E)-4-{(4S,5S)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}but-2-enoate

Base Information

Chemical Name:methyl (2E)-4-{(4S,5S)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}but-2-enoate
CAS No.:1138239-10-7
Molecular Formula:C₁₇H₂₂O₅
Molecular Weight:306.359
Hs Code.:

Synonyms:methyl (2E)-4-{(4S,5S)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}but-2-enoate

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Chemical Property of methyl (2E)-4-{(4S,5S)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}but-2-enoate

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Technology Process of methyl (2E)-4-{(4S,5S)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}but-2-enoate

There total 5 articles about methyl (2E)-4-{(4S,5S)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}but-2-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: 100.0%

: 1138239-09-4
methyl (2E)-4-{(4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}but-2-enoate

: 1138239-10-7
methyl (2E)-4-{(4S,5S)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}but-2-enoate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 2h;
DOI:10.1016/j.tetlet.2009.01.050

Reference yield: 97.0%

: 1384589-87-0
(R)-[(4R,5S)-5-allyl-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol

: 292638-85-8,9003-21-8,96-33-3
acrylic acid methyl ester

: 1138239-10-7
methyl (2E)-4-{(4S,5S)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}but-2-enoate

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1016/j.tetasy.2012.05.002

Reference yield:

: 86795-44-0,86795-47-3,147976-25-8,147976-26-9
3,4-O-isopropylidene-2-deoxy-D-ribose

: 1138239-10-7
methyl (2E)-4-{(4S,5S)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}but-2-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / -78 - 0 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: magnesium / diethyl ether / 20 °C / Inert atmosphere

3.2: 6 h / -78 °C / Inert atmosphere

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 3 h / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; oxalyl dichloride; potassium hexamethylsilazane; magnesium; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.2: Wittig reaction / 2.1: Swern oxidation / 2.2: Swern oxidation / 3.2: Grignard reaction / 3.3: Grignard reaction;
DOI:10.1016/j.tetasy.2012.05.002