(2S,3S,4S,E)-((1S,2R)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 3-hydroxy-7-iodo-2,4,6-trimethylhept-6-enoate

Base Information

Chemical Name:(2S,3S,4S,E)-((1S,2R)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 3-hydroxy-7-iodo-2,4,6-trimethylhept-6-enoate
CAS No.:1132969-89-1
Molecular Formula:C₃₅H₄₄INO₅S
Molecular Weight:717.709
Hs Code.:

Synonyms:(2S,3S,4S,E)-((1S,2R)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 3-hydroxy-7-iodo-2,4,6-trimethylhept-6-enoate

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Chemical Property of (2S,3S,4S,E)-((1S,2R)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 3-hydroxy-7-iodo-2,4,6-trimethylhept-6-enoate

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MSDS Files:: SDS file from LookChem

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Technology Process of (2S,3S,4S,E)-((1S,2R)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 3-hydroxy-7-iodo-2,4,6-trimethylhept-6-enoate

There total 6 articles about (2S,3S,4S,E)-((1S,2R)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 3-hydroxy-7-iodo-2,4,6-trimethylhept-6-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: 90.0%

: 1032592-19-0
(2S,4E)-2,4-dimethyl-5-iodo-4-pentenal

: 187324-67-0
(1S,2R)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate

: 145412-54-0
dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane

: 1132969-89-1
(2S,3S,4S,E)-((1S,2R)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 3-hydroxy-7-iodo-2,4,6-trimethylhept-6-enoate

: 108-93-0
cyclohexanol

Guidance literature:: (1S,2R)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate; With triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In hexane; dichloromethane; at -78 ℃; Inert atmosphere;

(2S,4E)-2,4-dimethyl-5-iodo-4-pentenal; Further stages;
DOI:10.1002/chem.201102797

Reference yield: 90.0%

: 1032592-19-0
(2S,4E)-2,4-dimethyl-5-iodo-4-pentenal

: 187324-67-0
(1S,2R)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate

: 1132969-89-1
(2S,3S,4S,E)-((1S,2R)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 3-hydroxy-7-iodo-2,4,6-trimethylhept-6-enoate

Guidance literature:: (1S,2R)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate; With triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In hexane; dichloromethane; at -78 ℃; for 4.05h; Inert atmosphere;

(2S,4E)-2,4-dimethyl-5-iodo-4-pentenal; In hexane; dichloromethane; at -78 ℃; Inert atmosphere;

With dihydrogen peroxide; In methanol; hexane; dichloromethane; at 20 ℃; for 16.5h; pH=7; diastereoselective reaction; aq. buffer;
DOI:10.1002/anie.200804645

Reference yield:

: 1132969-88-0
(S,E)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-5-iodo-N,2,4-trimethylpent-4-enamide

: 1132969-89-1
(2S,3S,4S,E)-((1S,2R)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 3-hydroxy-7-iodo-2,4,6-trimethylhept-6-enoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: ammonia borane; n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

2.1: pyridine; Dess-Martin periodane / methanol; dichloromethane / 2.75 h / 0 - 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 20 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

With pyridine; n-butyllithium; ammonia borane; Dess-Martin periodane; triethylamine; diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; 3.1: Masamune anti-aldol reaction;
DOI:10.1002/chem.201102797