2R-isopropyl-6R-methyl-13S-triisopropylsilanyloxy-2S-[4-(triphenyl-λ-sulfanyl)but-1E-enyl]-9S-tritylsulfanylmethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

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Chemical Name:2R-isopropyl-6R-methyl-13S-triisopropylsilanyloxy-2S-[4-(triphenyl-λ-sulfanyl)but-1E-enyl]-9S-tritylsulfanylmethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone
CAS No.:663919-05-9
Molecular Formula:C₆₇H₈₁N₃O₆S₂Si
Molecular Weight:1116.61
Hs Code.:

2R-isopropyl-6R-methyl-13S-triisopropylsilanyloxy-2S-[4-(triphenyl-λ-sulfanyl)but-1E-enyl]-9S-tritylsulfanylmethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

Synonyms:2R-isopropyl-6R-methyl-13S-triisopropylsilanyloxy-2S-[4-(triphenyl-λ-sulfanyl)but-1E-enyl]-9S-tritylsulfanylmethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

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Chemical Property of 2R-isopropyl-6R-methyl-13S-triisopropylsilanyloxy-2S-[4-(triphenyl-λ-sulfanyl)but-1E-enyl]-9S-tritylsulfanylmethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

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Technology Process of 2R-isopropyl-6R-methyl-13S-triisopropylsilanyloxy-2S-[4-(triphenyl-λ-sulfanyl)but-1E-enyl]-9S-tritylsulfanylmethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

There total 16 articles about 2R-isopropyl-6R-methyl-13S-triisopropylsilanyloxy-2S-[4-(triphenyl-λ-sulfanyl)but-1E-enyl]-9S-tritylsulfanylmethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone 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: 53.0%

: 663919-04-8
4R-{2S-[2-(3S-hydroxy-7-tritylsulfanylhept-4E-enoylamino)propionylamino]-3-tritylsulfanylpropionylamino}-5R-methyl-3S-triisopropylsilanyloxyhexanoic acid

: 663919-05-9
2R-isopropyl-6R-methyl-13S-triisopropylsilanyloxy-2S-[4-(triphenyl-λ-sulfanyl)but-1E-enyl]-9S-tritylsulfanylmethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

Guidance literature:: 4R-{2S-[2-(3S-hydroxy-7-tritylsulfanylhept-4E-enoylamino)propionylamino]-3-tritylsulfanylpropionylamino}-5R-methyl-3S-triisopropylsilanyloxyhexanoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 2h;

With dmap; In tetrahydrofuran; toluene; at 50 ℃; for 4h;
DOI:10.1021/ja039258q

Reference yield:

: 22838-58-0
Boc-D-Val-OH

: 663919-05-9
2R-isopropyl-6R-methyl-13S-triisopropylsilanyloxy-2S-[4-(triphenyl-λ-sulfanyl)but-1E-enyl]-9S-tritylsulfanylmethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

Guidance literature:: Multi-step reaction with 14 steps

1.1: EDAC*HCl; DMAP / CH₂Cl₂ / 4.5 h / 0 - 20 °C

2.1: LDA / tetrahydrofuran / 1 h / -78 °C

2.2: 2.38 g / tetrahydrofuran / 0.75 h / -78 °C

3.1: 70 percent / potassium borohydride / methanol / 0.83 h / -78 - 0 °C

4.1: aq. LiOH / tetrahydrofuran / 2 h / 20 °C

5.1: 569 g / DCC; DMAP / CH₂Cl₂ / 18 h / 20 °C

6.1: TFA / CH₂Cl₂ / 3 h / 0 °C

7.1: 808.5 mg / PyBOP; DIEA / 0.33 h / 20 °C

8.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 4.5 h / 0 - 20 °C

9.1: EtNH₂ / acetonitrile / 3 h / 20 °C

10.1: 174.1 mg / PyBOP; DIEA / CH₂Cl₂ / 2 h / 20 °C

11.1: EtNH₂ / acetonitrile / 5 h / 20 °C

12.1: 176 mg / DMAP / CH₂Cl₂ / 7 h / 20 °C

13.1: 71 percent / Zn; NH₄Ac / tetrahydrofuran / 5 h / 20 °C

14.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C

14.2: 53 percent / DMAP / toluene; tetrahydrofuran / 4 h / 50 °C

With 2,6-dimethylpyridine; dmap; lithium hydroxide; potassium borohydride; 2,4,6-trichlorobenzoyl chloride; ammonium acetate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 2.2: Claisen condensation / 14.1: Yamaguchi macrolactonization;
DOI:10.1021/ja039258q

Reference yield:

: 180973-22-2
(2E)-5-[(triphenylmethyl)thio]-2-pentenal

: 663919-05-9
2R-isopropyl-6R-methyl-13S-triisopropylsilanyloxy-2S-[4-(triphenyl-λ-sulfanyl)but-1E-enyl]-9S-tritylsulfanylmethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

Guidance literature:: Multi-step reaction with 4 steps

1.1: TiCl₄; DIEA / CH₂Cl₂ / 2 h / -78 °C

1.2: 76 percent / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 176 mg / DMAP / CH₂Cl₂ / 7 h / 20 °C

3.1: 71 percent / Zn; NH₄Ac / tetrahydrofuran / 5 h / 20 °C

4.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C

4.2: 53 percent / DMAP / toluene; tetrahydrofuran / 4 h / 50 °C

With dmap; 2,4,6-trichlorobenzoyl chloride; ammonium acetate; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; dichloromethane; 4.1: Yamaguchi macrolactonization;
DOI:10.1021/ja039258q