(4R,5S)-4-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}-5-ethenyl-2,2-dimethyl-1,3-dioxolane

Base Information

Chemical Name:(4R,5S)-4-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}-5-ethenyl-2,2-dimethyl-1,3-dioxolane
CAS No.:1448445-89-3
Molecular Formula:C₂₆H₃₆O₃Si
Molecular Weight:424.656
Hs Code.:

Synonyms:(4R,5S)-4-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}-5-ethenyl-2,2-dimethyl-1,3-dioxolane

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Chemical Property of (4R,5S)-4-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}-5-ethenyl-2,2-dimethyl-1,3-dioxolane

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Technology Process of (4R,5S)-4-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}-5-ethenyl-2,2-dimethyl-1,3-dioxolane

There total 9 articles about (4R,5S)-4-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}-5-ethenyl-2,2-dimethyl-1,3-dioxolane 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: 90.0%

: 1448445-88-2
(3S,4R,6R)-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}hept-1-ene-3,4-diol

: 77-76-9
2,2-dimethoxy-propane

: 1448445-89-3
(4R,5S)-4-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}-5-ethenyl-2,2-dimethyl-1,3-dioxolane

Guidance literature:: With camphorsulfonic acid; In dichloromethane; at 0 ℃; for 0.25 - 0.333333h;
DOI:10.1002/hlca.201200164

Reference yield:

: 303044-40-8
(2E,5R)-5-{[(1,1-dimethylethyl)diphenylsilyl]oxy}hex-2-en-1-ol

: 1448445-89-3
(4R,5S)-4-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}-5-ethenyl-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 5 steps

1.1: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

1.2: 8 h / -20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

2.2: 0.5 h / -78 - 20 °C

3.1: sodium hexamethyldisilazane / tetrahydrofuran; hexane / 2 h / 0 °C

3.2: 0.5 h / 0 °C

4.1: scandium tris(trifluoromethanesulfonate); water / tetrahydrofuran / 2.5 h / 20 °C

5.1: camphorsulfonic acid / dichloromethane / 0.25 - 0.33 h / 0 °C

With titanium(IV) isopropylate; oxalyl dichloride; water; sodium hexamethyldisilazane; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; hexane; dichloromethane; 1.1: |Sharpless Asymmetric Epoxidation / 1.2: |Sharpless Asymmetric Epoxidation / 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;
DOI:10.1002/hlca.201200164

Reference yield:

: 303044-41-9
(2R,3R)-3-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}oxirane-2-methanol

: 1448445-89-3
(4R,5S)-4-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}-5-ethenyl-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

1.2: 0.5 h / -78 - 20 °C

2.1: sodium hexamethyldisilazane / tetrahydrofuran; hexane / 2 h / 0 °C

2.2: 0.5 h / 0 °C

3.1: scandium tris(trifluoromethanesulfonate); water / tetrahydrofuran / 2.5 h / 20 °C

4.1: camphorsulfonic acid / dichloromethane / 0.25 - 0.33 h / 0 °C

With oxalyl dichloride; water; sodium hexamethyldisilazane; dimethyl sulfoxide; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; hexane; dichloromethane; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation;
DOI:10.1002/hlca.201200164