(+)-(1S,2S,3R)-2,3-O-isopropylidene-3-(2-triphenylmetoxyethyl)-4-cyclopentenyl p-toluenesulfonate

Base Information

Chemical Name:(+)-(1S,2S,3R)-2,3-O-isopropylidene-3-(2-triphenylmetoxyethyl)-4-cyclopentenyl p-toluenesulfonate
CAS No.:902455-28-1
Molecular Formula:C₃₆H₃₆O₆S
Molecular Weight:596.744
Hs Code.:

Synonyms:(+)-(1S,2S,3R)-2,3-O-isopropylidene-3-(2-triphenylmetoxyethyl)-4-cyclopentenyl p-toluenesulfonate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+)-(1S,2S,3R)-2,3-O-isopropylidene-3-(2-triphenylmetoxyethyl)-4-cyclopentenyl p-toluenesulfonate

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Technology Process of (+)-(1S,2S,3R)-2,3-O-isopropylidene-3-(2-triphenylmetoxyethyl)-4-cyclopentenyl p-toluenesulfonate

There total 6 articles about (+)-(1S,2S,3R)-2,3-O-isopropylidene-3-(2-triphenylmetoxyethyl)-4-cyclopentenyl p-toluenesulfonate 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: 96.0%

: 902455-27-0
(+)-(1S,2S,3R)-2,3-O-isopropylidene-3-(2-triphenylmetoxyethyl)-4-cyclopentenol

: 98-59-9
p-toluenesulfonyl chloride

: 902455-28-1
(+)-(1S,2S,3R)-2,3-O-isopropylidene-3-(2-triphenylmetoxyethyl)-4-cyclopentenyl p-toluenesulfonate

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1016/j.tet.2006.04.042

Reference yield:

: (4R,5S)-5-((S)-1-Hydroxy-allyl)-2,2-dimethyl-4-vinyl-[1,3]dioxolane-4-carbaldehyde

: 902455-28-1
(+)-(1S,2S,3R)-2,3-O-isopropylidene-3-(2-triphenylmetoxyethyl)-4-cyclopentenyl p-toluenesulfonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: second generation Grubbs catalyst / CH₂Cl₂ / 5 h / 20 °C

2.1: potassium tert-butoxide / tetrahydrofuran / 0 - 20 °C

2.2: 826 mg / tetrahydrofuran / 12 h / 20 °C

3.1: borane-dimethyl sulfide; 2-methyl-2-butene / tetrahydrofuran / 0 - 20 °C

3.2: 71 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 12 h / 20 °C

4.1: 76 percent / 4-(dimethylamino)pyridine; pyridine / 24 h / 20 °C

5.1: 96 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

With pyridine; dmap; 2-methyl-but-2-ene; dimethylsulfide borane complex; potassium tert-butylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; 2.2: Wittig reaction;
DOI:10.1016/j.tet.2006.04.042

Reference yield:

: 474329-16-3
(-)-(1S)-1-[(4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl]prop-2-en-1-ol

: 902455-28-1
(+)-(1S,2S,3R)-2,3-O-isopropylidene-3-(2-triphenylmetoxyethyl)-4-cyclopentenyl p-toluenesulfonate

Guidance literature:: Multi-step reaction with 6 steps

1.1: TEMPO; tetrabutylammonium chloride; N-chlorosuccinimide / NaHCO₃; K₂CO₃ / CH₂Cl₂; H₂O / 3 h / 20 °C / pH 8.6

2.1: second generation Grubbs catalyst / CH₂Cl₂ / 5 h / 20 °C

3.1: potassium tert-butoxide / tetrahydrofuran / 0 - 20 °C

3.2: 826 mg / tetrahydrofuran / 12 h / 20 °C

4.1: borane-dimethyl sulfide; 2-methyl-2-butene / tetrahydrofuran / 0 - 20 °C

4.2: 71 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 12 h / 20 °C

5.1: 76 percent / 4-(dimethylamino)pyridine; pyridine / 24 h / 20 °C

6.1: 96 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

With pyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-chloro-succinimide; 2-methyl-but-2-ene; dimethylsulfide borane complex; potassium tert-butylate; tetrabutyl-ammonium chloride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; dichloromethane; water; 3.2: Wittig reaction;
DOI:10.1016/j.tet.2006.04.042