(3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]propionylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate

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Chemical Name:(3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]propionylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate
CAS No.:1075206-59-5
Molecular Formula:C₇₅H₈₉N₃O₈S₂Si
Molecular Weight:1252.76
Hs Code.:

(3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]propionylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate

Synonyms:(3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]propionylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate

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Chemical Property of (3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]propionylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate

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Technology Process of (3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]propionylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate

There total 17 articles about (3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]propionylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate 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: 94.0%

: 1027785-35-8
(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enamido]propanoic acid

: 1075206-51-7
(3S,4R)-allyl 4-[(S)-2-amino-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-5-methylhexanoate

: 1075206-59-5
(3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]propionylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate

Guidance literature:: With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at -30 ℃; Inert atmosphere;
DOI:10.1002/chem.200901552

Reference yield:

: 1027785-35-8
(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enamido]propanoic acid

: 1075206-51-7
(3S,4R)-allyl 4-[(S)-2-amino-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-5-methylhexanoate

: (3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]propionylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate

: 1075206-59-5
(3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]propionylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate

Guidance literature:: With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20 ℃; optical yield given as %de; Inert atmosphere;
DOI:10.1002/chem.200901552

Reference yield:

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

: 1075206-59-5
(3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]propionylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate

Guidance literature:: Multi-step reaction with 10 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

With 1H-imidazole; 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; potassium borohydride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; chromium(VI) oxide; potassium carbonate; N-ethyl-N,N-diisopropylamine; HATU; 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;
DOI:10.3987/COM-07-S(N)5