(E)-(2R,3R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-non-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

Base Information

Chemical Name:(E)-(2R,3R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-non-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester
CAS No.:457630-92-1
Molecular Formula:C₄₂H₆₁NO₅SSi
Molecular Weight:720.102
Hs Code.:

(E)-(2R,3R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-non-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

Synonyms:(E)-(2R,3R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-non-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

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Chemical Property of (E)-(2R,3R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-non-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

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Technology Process of (E)-(2R,3R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-non-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

There total 2 articles about (E)-(2R,3R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-non-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester 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%

: 69739-34-0
t-butyldimethylsiyl triflate

: 457630-83-0
(E)-(2R,3R,6S)-3-Hydroxy-2,6-dimethyl-non-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

: 457630-92-1
(E)-(2R,3R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-non-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

Guidance literature:: With 2,6-dimethylpyridine; at 0 ℃;
DOI:10.1021/ol0262284

Reference yield:

: 227299-35-6
(E)-(S)-4-Methyl-hept-2-enal

: 457630-92-1
(E)-(2R,3R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-non-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: Cy₂BOTf; TEA / 2 h / -78 °C

1.2: 16 h / -78 - -60 °C

1.3: 65 percent / H₂O₂ / methanol / 0 - 20 °C / pH 7

2.1: 94 percent / 2,6-lutidine / 0 °C

With 2,6-dimethylpyridine; TEA; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane;
DOI:10.1021/ol0262284

Reference yield:

: 457630-92-1
(E)-(2R,3R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-non-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

: (3E,5E,14E)-(9R,10R,12R,19S,20R)-9-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-10,12-bis-(4-methoxy-benzyloxy)-4,19-dimethyl-20-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-8,11,17-trimethylene-oxacycloicosa-3,5,14-trien-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 83 percent / DIBAL / CH₂Cl₂ / 2 h / -78 °C

2.1: 68 percent / Et₃N / CH₂Cl₂ / 16.33 h / 0 - 20 °C

3.1: 82 percent / dimethylsulfoxide / 16 h

4.1: 80 percent / indium rod / tetrahydrofuran / 6 h / 42 °C / sonication

5.1: 89 percent / TBAF; AcOH / tetrahydrofuran / 20 - 40 °C

6.1: 89 percent / 4 Angstroem MS; L-diethyl tartrate; t-BuOOH / Ti(i-PrO)4 / CH₂Cl₂ / 24 h / -23 °C

7.1: 79 percent / DIAD; PPh₃ / ethanol / 16.5 h / 0 - 20 °C

8.1: Bu₃SnF; Red-Sil; TBAF / (PPh₃)2PdCl₂ / diethyl ether / 20 °C

8.2: Cu(I) thiophenecarboxylate; NMP / 0 - 20 °C

9.1: PhHC=Ru(PCy₃)(IMes-H₂)Cl₂ / CH₂Cl₂ / 40 °C

With tert.-butylhydroperoxide; indium; diethyl (2R,3R)-tartrate; di-isopropyl azodicarboxylate; 4 Angstroem MS; Red-Sil; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; tributyltin fluoride; acetic acid; triethylamine; triphenylphosphine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) isopropylate; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; 4.1: Markovnikov addition / 6.1: Sharpless epoxidation / 7.1: Mitsunobu esterification / 8.2: Stille coupling;
DOI:10.1021/ol0262284