(2R,3S,E)-((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 5-iodo-3-methoxy-2,4-dimethylpent-4-enoate

Base Information

Chemical Name:(2R,3S,E)-((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 5-iodo-3-methoxy-2,4-dimethylpent-4-enoate
CAS No.:942133-26-8
Molecular Formula:C₃₃H₄₀INO₅S
Molecular Weight:689.655
Hs Code.:

Synonyms:(2R,3S,E)-((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 5-iodo-3-methoxy-2,4-dimethylpent-4-enoate

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Chemical Property of (2R,3S,E)-((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 5-iodo-3-methoxy-2,4-dimethylpent-4-enoate

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Technology Process of (2R,3S,E)-((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 5-iodo-3-methoxy-2,4-dimethylpent-4-enoate

There total 1 articles about (2R,3S,E)-((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 5-iodo-3-methoxy-2,4-dimethylpent-4-enoate 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%

: 942133-13-3
(2R,3S,E)-((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 3-hydroxy-5-iodo-2,4-dimethylpent-4-enoate

: 74-88-4
methyl iodide

: 942133-26-8
(2R,3S,E)-((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 5-iodo-3-methoxy-2,4-dimethylpent-4-enoate

Guidance literature:: With 3 A molecular sieve; silver(l) oxide; In diethyl ether; at 20 ℃; for 48h;
DOI:10.1021/ja071461o

Reference yield:

: 942133-26-8
(2R,3S,E)-((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 5-iodo-3-methoxy-2,4-dimethylpent-4-enoate

: (S)-1-(4-((1S,2S,3E,5E,7S,8R,10E,12Z,14Z,16S,17S,18E)-17-(tert-butyldimethylsilyloxy)-1-hydroxy-7-methoxy-21-(4-methoxybenzyloxy)-2,6,8,12,14,16,19-heptamethyl-9-oxohenicosa-3,5,10,12,14,18-hexaenyl)thiazol-2-yl)-3-methylbutyl methylcarbamate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 96 percent / LiAlH₄ / diethyl ether / 0 - 20 °C

2.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h / 20 °C

3.1: diethyl ether / 0.5 h / -78 °C

4.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

5.1: (c-Hex)2BCl; NEt₃ / diethyl ether / 1 h / 0 °C

5.2: diethyl ether / -78 - -30 °C

5.3: aq. H₂O₂ / diethyl ether; methanol / 1 h / 0 °C / pH 7

6.1: Ac₂O; DMAP / tetrahydrofuran / 0.67 h / 20 °C

6.2: DBU / tetrahydrofuran / 1 h

7.1: NaHCO₃; TBACl; NEt₃ / PdCl₂[PPh₃]2 / dimethylformamide; acetonitrile; H₂O / 0.17 h / 80 °C

With dmap; lithium aluminium tetrahydride; dicyclohexylboron chloride; tetrabutyl-ammonium chloride; acetic anhydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 5.2: Peterson aldol reaction / 7.1: Heck reaction;
DOI:10.1021/ja071461o

Reference yield:

: 942133-26-8
(2R,3S,E)-((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 5-iodo-3-methoxy-2,4-dimethylpent-4-enoate

: (S)-1-(4-((1S,2S,3E,5E,7S,8R,10E,12E,14Z,16S,17S,18E)-17-(tert-butyldimethylsilyloxy)-1-hydroxy-7-methoxy-21-(4-methoxybenzyloxy)-2,6,8,12,14,16,19-heptamethyl-9-oxohenicosa-3,5,10,12,14,18-hexaenyl)thiazol-2-yl)-3-methylbutyl methylcarbamate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 96 percent / LiAlH₄ / diethyl ether / 0 - 20 °C

2.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h / 20 °C

3.1: diethyl ether / 0.5 h / -78 °C

4.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

5.1: (c-Hex)2BCl; NEt₃ / diethyl ether / 1 h / 0 °C

5.2: diethyl ether / -78 - -30 °C

5.3: aq. H₂O₂ / diethyl ether; methanol / 1 h / 0 °C / pH 7

6.1: Ac₂O; DMAP / tetrahydrofuran / 0.67 h / 20 °C

6.2: DBU / tetrahydrofuran / 1 h

7.1: NaHCO₃; TBACl; NEt₃ / PdCl₂[PPh₃]2 / dimethylformamide; acetonitrile; H₂O / 0.17 h / 80 °C

With dmap; lithium aluminium tetrahydride; dicyclohexylboron chloride; tetrabutyl-ammonium chloride; acetic anhydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 5.2: Peterson aldol reaction / 7.1: Heck reaction;
DOI:10.1021/ja071461o