(2S,6R,9S,12R,13S)-13-(tert-butyldimethylsiloxy)-12-isopropyl-6-methyl-2-[(E)-4-(tritylthio)but-1-enyl]-9-(tritylthiomethyl)-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

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Chemical Name:(2S,6R,9S,12R,13S)-13-(tert-butyldimethylsiloxy)-12-isopropyl-6-methyl-2-[(E)-4-(tritylthio)but-1-enyl]-9-(tritylthiomethyl)-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone
CAS No.:1075206-62-0
Molecular Formula:C₆₄H₇₅N₃O₆S₂Si
Molecular Weight:1074.53
Hs Code.:

(2S,6R,9S,12R,13S)-13-(tert-butyldimethylsiloxy)-12-isopropyl-6-methyl-2-[(E)-4-(tritylthio)but-1-enyl]-9-(tritylthiomethyl)-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

Synonyms:(2S,6R,9S,12R,13S)-13-(tert-butyldimethylsiloxy)-12-isopropyl-6-methyl-2-[(E)-4-(tritylthio)but-1-enyl]-9-(tritylthiomethyl)-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

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Chemical Property of (2S,6R,9S,12R,13S)-13-(tert-butyldimethylsiloxy)-12-isopropyl-6-methyl-2-[(E)-4-(tritylthio)but-1-enyl]-9-(tritylthiomethyl)-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

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Technology Process of (2S,6R,9S,12R,13S)-13-(tert-butyldimethylsiloxy)-12-isopropyl-6-methyl-2-[(E)-4-(tritylthio)but-1-enyl]-9-(tritylthiomethyl)-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

There total 20 articles about (2S,6R,9S,12R,13S)-13-(tert-butyldimethylsiloxy)-12-isopropyl-6-methyl-2-[(E)-4-(tritylthio)but-1-enyl]-9-(tritylthiomethyl)-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: 90.0%

: 1075206-50-6
(7S,11R,14S,17R,18S,E)-18-(tert-butyldimethylsilyloxy)-7-hydroxy-17-isopropyl-11-methyl-9,12,15-trioxo-1,1,1-triphenyl-14-tritylthiomethyl-2-thia-10,13,16-triazaicos-5-en-20-oic acid

: 1075206-62-0
(2S,6R,9S,12R,13S)-13-(tert-butyldimethylsiloxy)-12-isopropyl-6-methyl-2-[(E)-4-(tritylthio)but-1-enyl]-9-(tritylthiomethyl)-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

Guidance literature:: With dmap; 2-methyl-6-nitrobenzoic anhydride; In dichloromethane; at 20 ℃;
DOI:10.1002/chem.200901552

Reference yield:

: 106391-88-2
(2R)-2-[(tert-butoxycarbonyl)amino]-3-methylbutylaldehyde

: 1075206-62-0
(2S,6R,9S,12R,13S)-13-(tert-butyldimethylsiloxy)-12-isopropyl-6-methyl-2-[(E)-4-(tritylthio)but-1-enyl]-9-(tritylthiomethyl)-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

Guidance literature:: Multi-step reaction with 13 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C

1.2: 0.67 h / -78 °C

2.1: sulfuric acid; chromium(VI) oxide / water; acetone / 1 h / 20 °C

3.1: potassium borohydride / methanol / 5 h / -40 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C

5.1: sodium hydroxide / ethanol / 6 h / 20 °C

6.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 20 °C

7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / 20 °C

8.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 3 h / 20 °C / Inert atmosphere

9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 20 °C

10.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 2 h / -30 °C / Inert atmosphere

11.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h / 20 °C

12.1: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

13.1: dmap; 2-methyl-6-nitrobenzoic anhydride / dichloromethane / 15 h / 20 °C

With morpholine; 1H-imidazole; 2,6-dimethylpyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-hydroxy-7-aza-benzotriazole; potassium borohydride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; 2-methyl-6-nitrobenzoic anhydride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; chromium(VI) oxide; potassium carbonate; N-ethyl-N,N-diisopropylamine; HATU; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 1.2: Aldol coupling / 2.1: Jones oxidation / 13.1: Shiina method;
DOI:10.3987/COM-07-S(N)5

Reference yield:

: 1027785-24-5
(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-en-1-ol

: 1075206-62-0
(2S,6R,9S,12R,13S)-13-(tert-butyldimethylsiloxy)-12-isopropyl-6-methyl-2-[(E)-4-(tritylthio)but-1-enyl]-9-(tritylthiomethyl)-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone

Guidance literature:: Multi-step reaction with 8 steps

1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C

2: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide / 0 - 20 °C

3: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 2 h / 20 °C / Inert atmosphere

4: lithium hydroxide / methanol / 3 h / 20 °C

5: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 2 h / -30 °C / Inert atmosphere

6: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h / 20 °C

7: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

8: dmap; 2-methyl-6-nitrobenzoic anhydride / dichloromethane / 15 h / 20 °C

With morpholine; dmap; sodium chlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-hydroxy-7-aza-benzotriazole; sodium dihydrogenphosphate dihydrate; 2-methyl-6-nitrobenzoic anhydride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; HATU; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile; 1: Dess-Martin oxidation / 2: Pinnick oxidation / 8: Shiina method;
DOI:10.3987/COM-07-S(N)5