(3S,6S,9R,12R,16S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-9,12-diisopropyl-16-((E)-4-tritylsulfanyl-but-1-enyl)-6-tritylsulfanylmethyl-1-oxa-4,7,10,13-tetraaza-cyclohexadecane-2,5,8,11,14-pentaone

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Chemical Name:(3S,6S,9R,12R,16S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-9,12-diisopropyl-16-((E)-4-tritylsulfanyl-but-1-enyl)-6-tritylsulfanylmethyl-1-oxa-4,7,10,13-tetraaza-cyclohexadecane-2,5,8,11,14-pentaone
CAS No.:620568-02-7
Molecular Formula:C₆₈H₈₂N₄O₇S₂Si
Molecular Weight:1159.64
Hs Code.:

(3S,6S,9R,12R,16S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-9,12-diisopropyl-16-((E)-4-tritylsulfanyl-but-1-enyl)-6-tritylsulfanylmethyl-1-oxa-4,7,10,13-tetraaza-cyclohexadecane-2,5,8,11,14-pentaone

Synonyms:(3S,6S,9R,12R,16S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-9,12-diisopropyl-16-((E)-4-tritylsulfanyl-but-1-enyl)-6-tritylsulfanylmethyl-1-oxa-4,7,10,13-tetraaza-cyclohexadecane-2,5,8,11,14-pentaone

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Chemical Property of (3S,6S,9R,12R,16S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-9,12-diisopropyl-16-((E)-4-tritylsulfanyl-but-1-enyl)-6-tritylsulfanylmethyl-1-oxa-4,7,10,13-tetraaza-cyclohexadecane-2,5,8,11,14-pentaone

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Technology Process of (3S,6S,9R,12R,16S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-9,12-diisopropyl-16-((E)-4-tritylsulfanyl-but-1-enyl)-6-tritylsulfanylmethyl-1-oxa-4,7,10,13-tetraaza-cyclohexadecane-2,5,8,11,14-pentaone

There total 15 articles about (3S,6S,9R,12R,16S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-9,12-diisopropyl-16-((E)-4-tritylsulfanyl-but-1-enyl)-6-tritylsulfanylmethyl-1-oxa-4,7,10,13-tetraaza-cyclohexadecane-2,5,8,11,14-pentaone 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: 58.0%

: 620567-24-0
(7R,11R,14R,17S,20S,E)-20-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-7-hydroxy-11,14-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-17-tritylthiomethyl-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oic acid

: 620568-02-7
(3S,6S,9R,12R,16S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-9,12-diisopropyl-16-((E)-4-tritylsulfanyl-but-1-enyl)-6-tritylsulfanylmethyl-1-oxa-4,7,10,13-tetraaza-cyclohexadecane-2,5,8,11,14-pentaone

Guidance literature:: With di-isopropyl azodicarboxylate; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1021/jo034765b

Reference yield:

: (2S,3R)-2-[(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanyl-propionylamino]-3-hydroxy-butyric acid 2-trimethylsilanyl-ethyl ester

: 620568-02-7
(3S,6S,9R,12R,16S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-9,12-diisopropyl-16-((E)-4-tritylsulfanyl-but-1-enyl)-6-tritylsulfanylmethyl-1-oxa-4,7,10,13-tetraaza-cyclohexadecane-2,5,8,11,14-pentaone

Guidance literature:: Multi-step reaction with 9 steps

1: 3.36 g / imidazole / 27 / 2 h / 20 °C

2: Et₂NH / CH₂Cl₂ / 3 h / 0 °C

3: 3.65 g / EDC; HOBt / dimethylformamide; CH₂Cl₂ / 20 h / 20 °C

4: Et₂NH / CH₂Cl₂ / 4 h / 0 °C

5: 3.20 g / EDC; HOBt / dimethylformamide; CH₂Cl₂ / 20 h / 20 °C

6: 100 percent / Et₂NH / CH₂Cl₂ / 6 h / 0 - 20 °C

7: 100 percent / BOP; DIPEA / CH₂Cl₂; acetonitrile / 1 h / 20 °C

8: 79 percent / aq. LiOH / tetrahydrofuran / 20 °C

9: 58 percent / PPh₃; TsOH*H₂O; DIAD / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; lithium hydroxide; di-isopropyl azodicarboxylate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; toluene-4-sulfonic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 27; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 9: Mitsunobu macrolactonization;
DOI:10.1021/jo034765b

Reference yield:

: 3695-77-0
triphenylmethanethiol

: 620568-02-7
(3S,6S,9R,12R,16S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-9,12-diisopropyl-16-((E)-4-tritylsulfanyl-but-1-enyl)-6-tritylsulfanylmethyl-1-oxa-4,7,10,13-tetraaza-cyclohexadecane-2,5,8,11,14-pentaone

Guidance literature:: Multi-step reaction with 8 steps

1.1: Et₃N / CH₂Cl₂ / 1 h / 20 °C

2.1: 1.06 g / benzene / 7 h / Heating

3.1: (n-Bu)2BOTf; DIPEA / CH₂Cl₂ / 1 h / 20 °C

3.2: 69 percent / CH₂Cl₂ / 8 h / -78 - -10 °C

4.1: 100 percent / Al-Hg / tetrahydrofuran; H₂O / 2 h / 0 °C

5.1: 78 percent / aq. LiOH; aq. H₂O₂ / tetrahydrofuran / 1 h / 0 °C

6.1: 100 percent / BOP; DIPEA / CH₂Cl₂; acetonitrile / 1 h / 20 °C

7.1: 79 percent / aq. LiOH / tetrahydrofuran / 20 °C

8.1: 58 percent / PPh₃; TsOH*H₂O; DIAD / tetrahydrofuran / 2 h / 0 °C

With lithium hydroxide; aluminium amalgam; di-isopropyl azodicarboxylate; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; acetonitrile; benzene; 8.1: Mitsunobu macrolactonization;
DOI:10.1021/jo034765b