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180973-24-4

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Basic Information
CAS No.: 180973-24-4
Name: (3S,4E)-3-Hydroxy-7-[(triphenylmethyl)thio]-4-heptenoic acid
Article Data: 7
Molecular Structure:
Molecular Structure of 180973-24-4 ((3S,4E)-3-Hydroxy-7-[(triphenylmethyl)thio]-4-heptenoic acid)
Formula: C26H26O3S
Molecular Weight: 418.557
Synonyms: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid;(3S,E)-3-hydroxy-7-tritylthio-4-heptenoic acid;(E)-(S)-3-hydroxy-7-tritylsulfanyl-hept-4-enoic acid;4-Heptenoic acid,3-hydroxy-7-[(triphenylmethyl)thio]-,(3S,4E);
Density: 1.201
PSA: 82.83000
LogP: 5.49360
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Synthetic route
180973-40-4

(E)-(S)-3-Hydroxy-7-tritylsulfanyl-hept-4-enoic acid benzyl ester

180973-24-4

(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

Conditions
ConditionsYield
With lithium hydroxide In methanol; water100%
663918-95-4

(3S,4E)-3-hydroxy-1-((4R)-4-isopropyl-2-thioxothiazolidin-3-yl)-7-tritylsulfanyl-hept-4-en-1-one

180973-24-4

(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

Conditions
ConditionsYield
With lithium hydroxide; water In tetrahydrofuran Cooling with ice;96%
Stage #1: (3S,4E)-3-hydroxy-1-((4R)-4-isopropyl-2-thioxothiazolidin-3-yl)-7-tritylsulfanyl-hept-4-en-1-one With water; lithium hydroxide In tetrahydrofuran at 0 - 20℃;
Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=2;		86%
With lithium hydroxide monohydrate; water In tetrahydrofuran at 0 - 30℃; for 12h;13 g
878630-47-8

(E)-(S)-3-hydroxy-1-[(R)-4-isopropyl-5,5-diphenyl-2-oxo-oxazolidin-3-yl]-7-tritylthio-4-hepten-1-one

180973-24-4

(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

Conditions
ConditionsYield
Stage #1: (E)-(S)-3-hydroxy-1-[(R)-4-isopropyl-5,5-diphenyl-2-oxo-oxazolidin-3-yl]-7-tritylthio-4-hepten-1-one With water; sodium hydroxide In tetrahydrofuran; methanol at 0℃; for 1h;
Stage #2: With hydrogenchloride In water; ethyl acetate at 0℃;		92%
With sodium hydroxide76%
With sodium hydroxide In methanol; water at 0 - 20℃; for 1h;58%
180973-22-2

(2E)-5-[(triphenylmethyl)thio]-2-pentenal

180973-24-4

(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: BuLi / tetrahydrofuran / -78 °C
1.2: Cp2ZrCl2 / tetrahydrofuran / -78 - 20 °C
2.1: 76 percent / NaOH
View Scheme
Multi-step reaction with 2 steps
1.1: SmI2 / tetrahydrofuran / -78 °C
1.2: tetrahydrofuran / -78 °C
2.1: 76 percent / NaOH
View Scheme
Multi-step reaction with 2 steps
1: 99 percent / Ti(IV) complex with (S)-(-)-binaphthyl amino alcohol
2: 100 percent / LiOH / methanol; H2O
View Scheme
3695-77-0

triphenylmethanethiol

180973-24-4

(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 78 percent / Cs2CO3
2: 91 percent / DIBAL
3: 74 percent / (COCl)2, DMSO, Et3N
4: 99 percent / Ti(IV) complex with (S)-(-)-binaphthyl amino alcohol
5: 100 percent / LiOH / methanol; H2O
View Scheme
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / 1 h / 25 °C / Inert atmosphere; Automated synthesizer
2.1: dmap / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere; Automated synthesizer
2.2: 2 h / -20 - 25 °C / Inert atmosphere; Automated synthesizer
2.3: -78 - 0 °C / Inert atmosphere; Automated synthesizer
3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere; Automated synthesizer
3.2: 1 h / -78 - -30 °C / Inert atmosphere; Automated synthesizer
3.3: 1 h / -50 - 0 °C / Inert atmosphere; Automated synthesizer
4.1: water; sodium hydroxide / tetrahydrofuran; methanol / 1 h / 0 °C
4.2: 0 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydride / tetrahydrofuran / 20 °C / Flow reactor
2.1: diisobutylaluminium hydride / toluene / -97 °C / Flow reactor
3.1: lithium hexamethyldisilazane / tetrahydrofuran / -40 °C / Flow reactor
3.2: 0.02 h / -78 °C / Flow reactor
4.1: sodium hydroxide / methanol; water / 1 h / 0 - 20 °C
View Scheme
180973-37-9

(E)-5-(tritylthio)-2-penten-1-ol

180973-24-4

(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 74 percent / (COCl)2, DMSO, Et3N
2: 99 percent / Ti(IV) complex with (S)-(-)-binaphthyl amino alcohol
3: 100 percent / LiOH / methanol; H2O
View Scheme
Multi-step reaction with 3 steps
1.1: manganese(IV) oxide / dichloromethane / 8 h / 25 - 45 °C
2.1: titanium tetrachloride / dichloromethane / 0 - 5 °C
2.2: 2 h / -78 °C
2.3: 0.5 h / -78 °C
3.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h / 0 - 30 °C
View Scheme
180973-36-8

(E)-5-Tritylsulfanyl-pent-2-enoic acid methyl ester

180973-24-4

(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 91 percent / DIBAL
2: 74 percent / (COCl)2, DMSO, Et3N
3: 99 percent / Ti(IV) complex with (S)-(-)-binaphthyl amino alcohol
4: 100 percent / LiOH / methanol; H2O
View Scheme
2409-87-2

methyl (2E)-penta-2,4-dienoate

180973-24-4

(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 78 percent / Cs2CO3
2: 91 percent / DIBAL
3: 74 percent / (COCl)2, DMSO, Et3N
4: 99 percent / Ti(IV) complex with (S)-(-)-binaphthyl amino alcohol
5: 100 percent / LiOH / methanol; H2O
View Scheme
150350-28-0

S-trityl 3-mercaptopropionaldehyde

180973-24-4

(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dmap / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere; Automated synthesizer
1.2: 2 h / -20 - 25 °C / Inert atmosphere; Automated synthesizer
1.3: -78 - 0 °C / Inert atmosphere; Automated synthesizer
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere; Automated synthesizer
2.2: 1 h / -78 - -30 °C / Inert atmosphere; Automated synthesizer
2.3: 1 h / -50 - 0 °C / Inert atmosphere; Automated synthesizer
3.1: water; sodium hydroxide / tetrahydrofuran; methanol / 1 h / 0 °C
3.2: 0 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere
1.2: 0 - 20 °C / Inert atmosphere
2.1: diisobutylaluminium hydride / toluene / -97 °C / Flow reactor
3.1: lithium hexamethyldisilazane / tetrahydrofuran / -40 °C / Flow reactor
3.2: 0.02 h / -78 °C / Flow reactor
4.1: sodium hydroxide / methanol; water / 1 h / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere
1.2: 0 - 20 °C / Inert atmosphere
2.1: diisobutylaluminium hydride / toluene / -97 °C / Flow reactor
3.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C / Flow reactor
3.2: 0.02 h / Flow reactor
4.1: sodium hydroxide / methanol; water / 1 h / 0 - 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: triphenylphosphine / toluene; water / 6 h / 25 - 105 °C
1.2: 2 h / 0 - 5 °C
2.1: diisobutylaluminium hydride / toluene / 3 h / 0 - 5 °C / Inert atmosphere
3.1: manganese(IV) oxide / dichloromethane / 8 h / 25 - 45 °C
4.1: titanium tetrachloride / dichloromethane / 0 - 5 °C
4.2: 2 h / -78 °C
4.3: 0.5 h / -78 °C
5.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h / 0 - 30 °C
View Scheme
1309766-86-6

ethyl (E)-5-(triphenylmethylthio)-2-pentenoate

180973-24-4

(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: diisobutylaluminium hydride / toluene / -97 °C / Flow reactor
2.1: lithium hexamethyldisilazane / tetrahydrofuran / -40 °C / Flow reactor
2.2: 0.02 h / -78 °C / Flow reactor
3.1: sodium hydroxide / methanol; water / 1 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: diisobutylaluminium hydride / toluene / -97 °C / Flow reactor
2.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C / Flow reactor
2.2: 0.02 h / Flow reactor
3.1: sodium hydroxide / methanol; water / 1 h / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: diisobutylaluminium hydride / toluene / 3 h / 0 - 5 °C / Inert atmosphere
2.1: manganese(IV) oxide / dichloromethane / 8 h / 25 - 45 °C
3.1: titanium tetrachloride / dichloromethane / 0 - 5 °C
3.2: 2 h / -78 °C
3.3: 0.5 h / -78 °C
4.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h / 0 - 30 °C
View Scheme
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Chemistry

Molecular Structure of (3S,4E)-3-Hydroxy-7-[(triphenylmethyl)thio]-4-heptenoic acid (CAS No.180973-24-4):

Molecular Formula: C26H26O3S 
Molecular Weight: 418.5478
CAS No: 180973-24-4
H bond acceptors: 3
H bond donors: 2
Freely Rotating Bonds: 11
Polar Surface Area: 82.83 Å2
Index of Refraction: 1.624
Molar Refractivity: 123.08 cm3
Molar Volume: 348.423 cm3
Surface Tension: 52.238 dyne/cm
Density: 1.201 g/cm3
Flash Point: 308.363 °C
Enthalpy of Vaporization: 92.097 kJ/mol
Boiling Point: 586.266 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
Systematic Name: (3S,4E)-3-Hydroxy-7-(tritylsulfanyl)hept-4-enoic acid 
InChI: InChI=1/C26H26O3S/c27-24(20-25(28)29)18-10-11-19-30-26(21-12-4-1-5-13-21,22-14-6-2-7-15-22)23-16-8-3-9-17-23/h1-10,12-18,24,27H,11,19-20H2,(H,28,29)/b18-10+/t24-/m1/s1
InChIKey: BGUJCVRJDCZLQS-XMZCUOJSBV
Std. InChI: InChI=1S/C26H26O3S/c27-24(20-25(28)29)18-10-11-19-30-26(21-12-4-1-5-13-21,22-14-6-2-7-15-22)23-16-8-3-9-17-23/h1-10,12-18,24,27H,11,19-20H2,(H,28,29)/b18-10+/t24-/m1/s1
Std. InChIKey: BGUJCVRJDCZLQS-XMZCUOJSSA-N