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

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(S,E)-3-HYDROXY-7-(TRITYLTHIO)HEPT-4-ENOIC ACID

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(S,E)‐3‐hydroxy‐7‐(tritylthio)hept‐4‐enoic acid

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High Quality Low Price (3S,4E)-3-Hydroxy-7-(tritylsulfanyl)-4-heptenoic acid C26H26O3S CAS 180973-24-4

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4-Heptenoic acid, 3-hydroxy-7-[(triphenylmethyl)thio]-, (3S,4E)-

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Xi`an Eastling Biotech Co., Ltd.

(3S,4E)-3-Hydroxy-7-[(triphenylmethyl)thio]-4-heptenoic acid

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(3S,4E)-3-Hydroxy-7-[(triphenylmethyl)thio]-4-heptenoic acid

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Antimex Chemical Limied

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Hangzhou Fandachem Co.,Ltd

180973-24-4 4-Heptenoic acid, 3-hydroxy-7-[(triphenylmethyl)thio]-, (3S,4E)-Appearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:intermediate Transportation:by air, by sea, by express

180973-24-4 4-Heptenoic acid, 3-hydroxy-7-[(triphenylmethyl)thio]-, (3S,4E)-

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SAGECHEM LIMITED

(3S,4E)-3-Hydroxy-7-[(triphenylmethyl)thio]-4-heptenoic acid

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Chemlyte Solutions

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Chemsigma International Co.,Ltd.

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ZHEJIANG JIUZHOU CHEM CO.,LTD

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LEAP CHEM Co., Ltd.

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(3S,4E)-3-Hydroxy-7-[(triphenylmethyl)thio]-4-heptenoic acid

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Yurui(Shanghai)Chemical Co.,Ltd

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(3S,4E)-3-Hydroxy-7-[(triphenylmethyl)thio]-4-heptenoic acid 180973-24-4

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suzhou BetterBioChem Co., Ltd.

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(S,E)-3-hydroxy-7-(tritylthio)hept-4-enoic acid

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Chemical Technology Co.,LTD

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Finetech Industry Limited

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Chengdu NoVi Biotechnology Co., Ltd.

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(3S,4E)-3-Hydroxy-7-[(triphenylmethyl)thio]-4-heptenoic acid

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Langchem

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(3S,4E)-3-Hydroxy-7-[(triphenylmethyl)thio]-4-heptenoic acid

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Alchemist-pharm chemical Technology Co. Ltd.

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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

Conditions	Yield
With lithium hydroxide In methanol; water	100%

: 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

Conditions	Yield
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

Conditions	Yield
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 hydroxide	76%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

: 76-83-5
trityl chloride

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: toluene / 6 h / 25 - 30 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 0.17 h / 0 - 5 °C 2.2: 3 h / 0 - 30 °C 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -75 - -70 °C 3.2: 2 h / -75 - 5 °C 4.1: triphenylphosphine / toluene; water / 6 h / 25 - 105 °C 4.2: 2 h / 0 - 5 °C 5.1: diisobutylaluminium hydride / toluene / 3 h / 0 - 5 °C / Inert atmosphere 6.1: manganese(IV) oxide / dichloromethane / 8 h / 25 - 45 °C 7.1: titanium tetrachloride / dichloromethane / 0 - 5 °C 7.2: 2 h / -78 °C 7.3: 0.5 h / -78 °C 8.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h / 0 - 30 °C View Scheme

Yield

Multi-step reaction with 8 steps
1.1: toluene / 6 h / 25 - 30 °C
2.1: sodium tetrahydroborate / tetrahydrofuran / 0.17 h / 0 - 5 °C
2.2: 3 h / 0 - 30 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -75 - -70 °C
3.2: 2 h / -75 - 5 °C
4.1: triphenylphosphine / toluene; water / 6 h / 25 - 105 °C
4.2: 2 h / 0 - 5 °C
5.1: diisobutylaluminium hydride / toluene / 3 h / 0 - 5 °C / Inert atmosphere
6.1: manganese(IV) oxide / dichloromethane / 8 h / 25 - 45 °C
7.1: titanium tetrachloride / dichloromethane / 0 - 5 °C
7.2: 2 h / -78 °C
7.3: 0.5 h / -78 °C
8.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h / 0 - 30 °C
View Scheme

: 27144-18-9
3-(tritylthio) propanoic acid

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: sodium tetrahydroborate / tetrahydrofuran / 0.17 h / 0 - 5 °C 1.2: 3 h / 0 - 30 °C 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -75 - -70 °C 2.2: 2 h / -75 - 5 °C 3.1: triphenylphosphine / toluene; water / 6 h / 25 - 105 °C 3.2: 2 h / 0 - 5 °C 4.1: diisobutylaluminium hydride / toluene / 3 h / 0 - 5 °C / Inert atmosphere 5.1: manganese(IV) oxide / dichloromethane / 8 h / 25 - 45 °C 6.1: titanium tetrachloride / dichloromethane / 0 - 5 °C 6.2: 2 h / -78 °C 6.3: 0.5 h / -78 °C 7.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h / 0 - 30 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: sodium tetrahydroborate / tetrahydrofuran / 0.17 h / 0 - 5 °C
1.2: 3 h / 0 - 30 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -75 - -70 °C
2.2: 2 h / -75 - 5 °C
3.1: triphenylphosphine / toluene; water / 6 h / 25 - 105 °C
3.2: 2 h / 0 - 5 °C
4.1: diisobutylaluminium hydride / toluene / 3 h / 0 - 5 °C / Inert atmosphere
5.1: manganese(IV) oxide / dichloromethane / 8 h / 25 - 45 °C
6.1: titanium tetrachloride / dichloromethane / 0 - 5 °C
6.2: 2 h / -78 °C
6.3: 0.5 h / -78 °C
7.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h / 0 - 30 °C
View Scheme

: 100360-56-3
3-(tritylthio)propan-1-ol

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -75 - -70 °C 1.2: 2 h / -75 - 5 °C 2.1: triphenylphosphine / toluene; water / 6 h / 25 - 105 °C 2.2: 2 h / 0 - 5 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / 0 - 5 °C / Inert atmosphere 4.1: manganese(IV) oxide / dichloromethane / 8 h / 25 - 45 °C 5.1: titanium tetrachloride / dichloromethane / 0 - 5 °C 5.2: 2 h / -78 °C 5.3: 0.5 h / -78 °C 6.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h / 0 - 30 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -75 - -70 °C
1.2: 2 h / -75 - 5 °C
2.1: triphenylphosphine / toluene; water / 6 h / 25 - 105 °C
2.2: 2 h / 0 - 5 °C
3.1: diisobutylaluminium hydride / toluene / 3 h / 0 - 5 °C / Inert atmosphere
4.1: manganese(IV) oxide / dichloromethane / 8 h / 25 - 45 °C
5.1: titanium tetrachloride / dichloromethane / 0 - 5 °C
5.2: 2 h / -78 °C
5.3: 0.5 h / -78 °C
6.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h / 0 - 30 °C
View Scheme

: 180973-32-4
(S)-2-{(Z)-2-[(S)-2-((R)-2-Amino-3-methyl-butyrylamino)-3-tritylsulfanyl-propionylamino]-but-2-enoylamino}-3-methyl-butyric acid methyl ester

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 180973-33-5
(5E,7S,11R,14S,17E,20S)-methyl 17-ethylidene-7-hydroxy-11,20-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-14-(tritylthiomethyl)-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oate

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine	95%

: 1196992-63-8
C52H49N5O7S

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 1196992-65-0
C63H63N5O7S2

Conditions

Conditions	Yield
Stage #1: C52H49N5O7S With diethylamine In acetonitrile at 20℃; for 2h; Inert atmosphere; Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 0 - 20℃; Inert atmosphere;	95%

: 1196992-16-1
(R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-4-{(S)-1-[1-(methoxycarbonylmethyl-carbamoyl)-cyclopropylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 1196992-18-3
(R)-4-((E)-(S)-3-hydroxy-7-tritylsulfanyl-hept-4-enoylamino)-4-{(S)-1-[1-(methoxycarbonylmethyl-carbamoyl)-cyclopropylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester

Conditions

Conditions	Yield
Stage #1: (R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-4-{(S)-1-[1-(methoxycarbonylmethyl-carbamoyl)-cyclopropylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester With diethylamine In acetonitrile at 20℃; for 1h; Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 0 - 20℃;	91%

Yield

Stage #1: (R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-4-{(S)-1-[1-(methoxycarbonylmethyl-carbamoyl)-cyclopropylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester With diethylamine In acetonitrile at 20℃; for 1h;
Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 0 - 20℃;

91%

: 1196992-76-3
[(1-{(S)-2-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-3-tritylsulfanyl-propionylamino}-cyclopropanecarbonyl)-amino]-acetic acid methyl ester

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 1196992-77-4
[(1-{(S)-2-[(R)-2-((E)-(S)-3-hydroxy-7-tritylsulfanyl-hept-4-enoylamino)-3-phenyl-propionylamino]-3-tritylsulfanyl-propionylamino}-cyclopropanecarbonyl)-amino]-acetic acid methyl ester

Conditions

Conditions	Yield
Stage #1: [(1-{(S)-2-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-3-tritylsulfanyl-propionylamino}-cyclopropanecarbonyl)-amino]-acetic acid methyl ester With diethylamine In acetonitrile at 20℃; for 2h; Inert atmosphere; Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 0 - 20℃; Inert atmosphere;	87%

Yield

Stage #1: [(1-{(S)-2-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-3-tritylsulfanyl-propionylamino}-cyclopropanecarbonyl)-amino]-acetic acid methyl ester With diethylamine In acetonitrile at 20℃; for 2h; Inert atmosphere;
Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 0 - 20℃; Inert atmosphere;

87%

: 1196992-05-8
(R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-4-{(S)-1-[1-(methoxycarbonylmethyl-carbamoyl)-1-methyl-ethylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 1196992-07-0
(R)-4-((E)-(S)-3-hydroxy-7-tritylsulfanyl-hept-4-enoylamino)-4-{(S)-1-[1-(methoxycarbonylmethyl-carbamoyl)-1-methyl-ethylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester

Conditions

Conditions	Yield
Stage #1: (R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-4-{(S)-1-[1-(methoxycarbonylmethyl-carbamoyl)-1-methyl-ethylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester With diethylamine In acetonitrile at 20℃; Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 0 - 20℃;	85%

Yield

Stage #1: (R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-4-{(S)-1-[1-(methoxycarbonylmethyl-carbamoyl)-1-methyl-ethylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester With diethylamine In acetonitrile at 20℃;
Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 0 - 20℃;

85%

: 2916-68-9
2-(Trimethylsilyl)ethanol

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 1043577-31-6
(S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-amino-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Cooling with ice;	80%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 5℃; for 0.916667h;	2.5 g

: 1196992-69-4
[(1-{(S)-2-[(R)-3-(3-chloro-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-tritylsulfanyl-propionylamino}-cyclopropanecarbonyl)-amino]-acetic acid methyl ester

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 1196992-72-9
[(1-{(S)-2-[(R)-3-(3-chloro-phenyl)-2-((E)-(S)-3-hydroxy-7-tritylsulfanyl-hept-4-enoylamino)-propionylamino]-3-tritylsulfanyl-propionylamino}-cyclopropanecarbonyl)-amino]-acetic acid methyl ester

Conditions

Conditions	Yield
Stage #1: [(1-{(S)-2-[(R)-3-(3-chloro-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-tritylsulfanyl-propionylamino}-cyclopropanecarbonyl)-amino]-acetic acid methyl ester With diethylamine In dichloromethane; acetonitrile at 20℃; for 1.5h; Inert atmosphere; Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 20℃; for 16h; Inert atmosphere;	80%

Yield

Stage #1: [(1-{(S)-2-[(R)-3-(3-chloro-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-tritylsulfanyl-propionylamino}-cyclopropanecarbonyl)-amino]-acetic acid methyl ester With diethylamine In dichloromethane; acetonitrile at 20℃; for 1.5h; Inert atmosphere;
Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 20℃; for 16h; Inert atmosphere;

80%

: 1196992-35-4
(R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-4-{(S)-1-[1-(methoxycarbonylmethyl-carbamoyl)-cyclobutylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 1196992-37-6
(R)-4-((E)-(S)-3-hydroxy-7-tritylsulfanyl-hept-4-enoylamino)-4-{(S)-1-[1-(methoxycarbonylmethyl-carbamoyl)-cyclobutylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester

Conditions

Conditions	Yield
Stage #1: (R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-4-{(S)-1-[1-(methoxycarbonylmethyl-carbamoyl)-cyclobutylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester With diethylamine In acetonitrile at 20℃; Inert atmosphere; Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 0 - 20℃; Inert atmosphere;	75%

Yield

Stage #1: (R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-4-{(S)-1-[1-(methoxycarbonylmethyl-carbamoyl)-cyclobutylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester With diethylamine In acetonitrile at 20℃; Inert atmosphere;
Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 0 - 20℃; Inert atmosphere;

75%

: 1196991-91-9
(R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-4-{(S)-1-[1-(1-hydroxy-2-methoxycarbonyl-ethyl)-cyclopropylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 1196991-93-1
(R)-4-{(S)-1-[1-(1-hydroxy-2-methoxycarbonyl-ethyl)-cyclopropylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-4-((E)-(S)-3-hydroxy-7-tritylsulfanyl-hept-4-enoylamino)-butyric acid tert-butyl ester

Conditions

Conditions	Yield
Stage #1: (R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-4-{(S)-1-[1-(1-hydroxy-2-methoxycarbonyl-ethyl)-cyclopropylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester With diethylamine In dichloromethane; acetonitrile for 1.5h; Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 16h; Inert atmosphere;	72%

Yield

Stage #1: (R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-4-{(S)-1-[1-(1-hydroxy-2-methoxycarbonyl-ethyl)-cyclopropylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester With diethylamine In dichloromethane; acetonitrile for 1.5h;
Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 16h; Inert atmosphere;

72%

: (3S,4R)-4-[(S)-2-((R)-2-Amino-propionylamino)-3-tritylsulfanyl-propionylamino]-3-hydroxy-5-methyl-hexanoic acid allyl ester

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 881845-29-0
(3S,4R)-3-Hydroxy-4-{(S)-2-[(R)-2-((E)-(S)-3-hydroxy-7-tritylsulfanyl-hept-4-enoylamino)-propionylamino]-3-tritylsulfanyl-propionylamino}-5-methyl-hexanoic acid allyl ester

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine	65%

: 1196992-82-1
[(1-{(S)-2-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-pyridin-4-yl-propionylamino]-3-tritylsulfanyl-propionylamino}-cyclopropanecarbonyl)-amino]-acetic acid methyl ester

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 1196992-84-3
[(1-{(S)-2-[(R)-2-((E)-(S)-3-hydroxy-7-tritylsulfanyl-hept-4-enoylamino)-3-pyridin-4-yl-propionylamino]-3-tritylsulfanyl-propionylamino}-cyclopropanecarbonyl)-amino]-acetic acid methyl ester

Conditions

Conditions	Yield
Stage #1: [(1-{(S)-2-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-pyridin-4-yl-propionylamino]-3-tritylsulfanyl-propionylamino}-cyclopropanecarbonyl)-amino]-acetic acid methyl ester With diethylamine In acetonitrile at 20℃; Inert atmosphere; Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 0 - 20℃; Inert atmosphere;	61%

Yield

Stage #1: [(1-{(S)-2-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-pyridin-4-yl-propionylamino]-3-tritylsulfanyl-propionylamino}-cyclopropanecarbonyl)-amino]-acetic acid methyl ester With diethylamine In acetonitrile at 20℃; Inert atmosphere;
Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 0 - 20℃; Inert atmosphere;

61%

: 1196992-56-9
C46H44N4O7S

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 1196992-58-1
[(1-{(S)-2-[2-((E)-(S)-3-hydroxy-7-tritylsulfanyl-hept-4-enoylamino)-acetylamino]-3-tritylsulfanyl-propionylamino}-cyclopropanecarbonyl)-amino]-acetic acid methyl ester

Conditions

Conditions	Yield
Stage #1: C46H44N4O7S With diethylamine In acetonitrile at 20℃; for 2h; Inert atmosphere; Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 20℃; for 16h; Inert atmosphere;	56%

: 1196992-44-5
((R)-2-{(S)-2-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-propionylamino]-3-tritylsulfanyl-propionylamino}-3-methyl-butyrylamino)-acetic acid methyl ester

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 1196992-46-7
((R)-2-{(S)-2-[2-((E)-(S)-3-hydroxy-7-tritylsulfanyl-hept-4-enoylamino)-2-methyl-propionylamino]-3-tritylsulfanyl-propionylamino}-3-methyl-butyrylamino)-acetic acid methyl ester

Conditions

Conditions	Yield
Stage #1: ((R)-2-{(S)-2-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-propionylamino]-3-tritylsulfanyl-propionylamino}-3-methyl-butyrylamino)-acetic acid methyl ester With diethylamine In acetonitrile at 20℃; for 1.25h; Inert atmosphere; Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 0 - 20℃; Inert atmosphere;	51%

Yield

Stage #1: ((R)-2-{(S)-2-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-propionylamino]-3-tritylsulfanyl-propionylamino}-3-methyl-butyrylamino)-acetic acid methyl ester With diethylamine In acetonitrile at 20℃; for 1.25h; Inert atmosphere;
Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 0 - 20℃; Inert atmosphere;

51%

: [2-((S)-2-{[1-(9H-fluoren-9-ylmethoxycarbonylamino)-cyclopropanecarbonyl]-amino}-3-tritylsulfanyl-propionylamino)-3-methyl-butyrylamino]-acetic acid methyl ester

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: [2-((S)-2-{[1-((E)-(S)-3-hydroxy-7-tritylsulfanyl-hept-4-enoylamino)-cyclopropanecarbonyl]-amino}-3-tritylsulfanyl-propionylamino)-3-methyl-butyrylamino]-acetic acid methyl ester

Conditions

Conditions	Yield
Stage #1: [2-((S)-2-{[1-(9H-fluoren-9-ylmethoxycarbonylamino)-cyclopropanecarbonyl]-amino}-3-tritylsulfanyl-propionylamino)-3-methyl-butyrylamino]-acetic acid methyl ester With diethylamine In acetonitrile at 20℃; Inert atmosphere; Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 0 - 20℃; Inert atmosphere;	41%

Yield

Stage #1: [2-((S)-2-{[1-(9H-fluoren-9-ylmethoxycarbonylamino)-cyclopropanecarbonyl]-amino}-3-tritylsulfanyl-propionylamino)-3-methyl-butyrylamino]-acetic acid methyl ester With diethylamine In acetonitrile at 20℃; Inert atmosphere;
Stage #2: (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 0 - 20℃; Inert atmosphere;

41%

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: spiruchostatin A

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 65 percent / N,N-diisopropylethylamine; benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium PF6(1-) 2: 87 percent / morpholine / Pd(PPh3)4 / methanol 3: 67 percent / MNBA; DMAP / CH2Cl2 4: 100 percent / I2 / methanol; CH2Cl2 View Scheme

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: (3S,4R)-3-Hydroxy-4-[((E)-(4S,7R,11S)-11-hydroxy-7-methyl-6,9-dioxo-1,2-dithia-5,8-diaza-cyclopentadec-12-ene-4-carbonyl)-amino]-5-methyl-hexanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 65 percent / N,N-diisopropylethylamine; benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium PF6(1-) 2: 87 percent / morpholine / Pd(PPh3)4 / methanol 3: 100 percent / I2 / methanol; CH2Cl2 View Scheme

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 881845-68-7
(2S,6R,9S,12R,13S)-13-Hydroxy-12-isopropyl-6-methyl-2-((E)-4-tritylsulfanyl-but-1-enyl)-9-tritylsulfanylmethyl-1-oxa-5,8,11-triaza-cyclopentadecane-4,7,10,15-tetraone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 65 percent / N,N-diisopropylethylamine; benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium PF6(1-) 2: 87 percent / morpholine / Pd(PPh3)4 / methanol 3: 67 percent / MNBA; DMAP / CH2Cl2 View Scheme

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 878630-45-6
(3S,4R)-3-Hydroxy-4-{(S)-2-[(R)-2-((E)-(S)-3-hydroxy-7-tritylsulfanyl-hept-4-enoylamino)-propionylamino]-3-tritylsulfanyl-propionylamino}-5-methyl-hexanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / N,N-diisopropylethylamine; benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium PF6(1-) 2: 87 percent / morpholine / Pd(PPh3)4 / methanol View Scheme

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 128517-07-7
romidepsin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, DIEA 2: 98 percent / LiOH 3: EDCl, DMAP, TsOH 4: 84 percent / I2 / methanol; H2O View Scheme

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 180973-35-7
(3S,9S,12R,16S)-6-eth-(Z)-ylidene-3,12-diisopropyl-16-((E)-4-tritylsulfanyl-but-1-enyl)-9-tritylsulfanylmethyl-1-oxa-4,7,10,13-tetraazacyclohexadecane-2,5,8,11,14-pentaone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, DIEA 2: 98 percent / LiOH 3: EDCl, DMAP, TsOH View Scheme

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: 180973-34-6
(5E,7S,11R,14S,17E,20S)-17-ethylidene-7-hydroxy-11,20-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-14-(tritylthiomethyl)-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, DIEA 2: 98 percent / LiOH View Scheme

: C51H51ClN3O5PolS

: 180973-24-4
(E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid

: C77H75ClN3O7PolS2

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 24h;

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