(3R,4R,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-3-hydroxy-4-(2-(trimethylsilyl)ethylsulfonamido)cyclohex-1-enecarboxylate

Base Information

• Chemical Name: (3R,4R,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-3-hydroxy-4-(2-(trimethylsilyl)ethylsulfonamido)cyclohex-1-enecarboxylate
• CAS No.: 1041262-69-4
• Molecular Formula: C₂₂H₃₀N₂O₇SSi
• Molecular Weight: 494.641

Synonyms:(3R,4R,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-3-hydroxy-4-(2-(trimethylsilyl)ethylsulfonamido)cyclohex-1-enecarboxylate

Chemical Property of (3R,4R,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-3-hydroxy-4-(2-(trimethylsilyl)ethylsulfonamido)cyclohex-1-enecarboxylate

Chemical Property:

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Technology Process of (3R,4R,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-3-hydroxy-4-(2-(trimethylsilyl)ethylsulfonamido)cyclohex-1-enecarboxylate

There total 5 articles about (3R,4R,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-3-hydroxy-4-(2-(trimethylsilyl)ethylsulfonamido)cyclohex-1-enecarboxylate 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: 87.0%

(1S,5S,6R)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-7-(2-(trimethylsilyl)ethylsulfonyl)-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylate (1041262-65-0) → (3R,4R,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-3-hydroxy-4-(2-(trimethylsilyl)ethylsulfonamido)cyclohex-1-enecarboxylate (1041262-69-4)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In 2-pentanol; at 0 - 100 ℃; Inert atmosphere;

DOI:10.1002/chem.201003454

Reference yield: 65.0%

2-pentanol (584-02-1) + (1S,5S,6R)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-7-(2-(trimethylsilyl)ethylsulfonyl)-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylate (1041262-65-0) → (3R,4R,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-3-hydroxy-4-(2-(trimethylsilyl)ethylsulfonamido)cyclohex-1-enecarboxylate (1041262-69-4) + (1R,4S,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-1-(pentan-3-yloxy)-4-(2-(trimethylsilyl)ethylsulfonamido)cyclohex-2-enecarboxylate (1041262-70-7) + ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-[2-(trimethylsilyl)ethylsulfonamido]cyclohex-1-enecarboxylate (1041262-66-1)

Guidance literature:

With boron trifluoride diethyl etherate; at 75 ℃; for 0.25h;

DOI:10.1002/anie.200800282

Reference yield: 60.0%

2-pentanol (584-02-1) + (1S,5S,6R)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-7-(2-(trimethylsilyl)ethylsulfonyl)-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylate (1041262-65-0) → (3R,4R,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-3-hydroxy-4-(2-(trimethylsilyl)ethylsulfonamido)cyclohex-1-enecarboxylate (1041262-69-4) + ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-[2-(trimethylsilyl)ethylsulfonamido]cyclohex-1-enecarboxylate (1041262-66-1)

Guidance literature:

With indium(III) triflate; at 75 ℃; Inert atmosphere;

DOI:10.1002/chem.201003454

upstream raw materials:

2-pentanol

(1S,5S,6R)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-7-(2-(trimethylsilyl)ethylsulfonyl)-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylate

2-(trimethylsilyl)ethanesulfonamide

Downstream raw materials:

ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-[2-(trimethylsilyl)ethylsulfonamido]cyclohex-1-enecarboxylate

(1R,4S,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-1-(pentan-3-yloxy)-4-(2-(trimethylsilyl)ethylsulfonamido)cyclohex-2-enecarboxylate

ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-{N-[2-(trimethylsilyl)ethylsulfonyl]acetamido}cyclohex-1-enecarboxylate

(3R,4R,5S)-4-acetamido-5-(1,3-dioxoisoindol-2-yl)-3-(pentyl-3-yloxy)cyclohexyl-ethyl-1-ene-1-carboxylate

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