Methanesulfonic acid 2-{3-eth-(E)-ylidene-6-[(2-iodo-phenyl)-methanesulfonyl-amino]-cyclohex-1-enyl}-ethyl ester

Base Information

• Chemical Name: Methanesulfonic acid 2-{3-eth-(E)-ylidene-6-[(2-iodo-phenyl)-methanesulfonyl-amino]-cyclohex-1-enyl}-ethyl ester
• CAS No.: 311309-61-2
• Molecular Formula: C₁₈H₂₄INO₅S₂
• Molecular Weight: 525.429

Synonyms:Methanesulfonic acid 2-{3-eth-(E)-ylidene-6-[(2-iodo-phenyl)-methanesulfonyl-amino]-cyclohex-1-enyl}-ethyl ester

Chemical Property of Methanesulfonic acid 2-{3-eth-(E)-ylidene-6-[(2-iodo-phenyl)-methanesulfonyl-amino]-cyclohex-1-enyl}-ethyl ester

Chemical Property:

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Technology Process of Methanesulfonic acid 2-{3-eth-(E)-ylidene-6-[(2-iodo-phenyl)-methanesulfonyl-amino]-cyclohex-1-enyl}-ethyl ester

There total 10 articles about Methanesulfonic acid 2-{3-eth-(E)-ylidene-6-[(2-iodo-phenyl)-methanesulfonyl-amino]-cyclohex-1-enyl}-ethyl 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: 78.0%

methanesulfonyl chloride (124-63-0) + N-[4-ethylidene-2-(2-hydroxy-ethyl)-cyclohex-2-enyl]-N-(2-iodo-phenyl)-methanesulfonamide (311309-60-1) → Methanesulfonic acid 2-{3-eth-(E)-ylidene-6-[(2-iodo-phenyl)-methanesulfonyl-amino]-cyclohex-1-enyl}-ethyl ester (311309-61-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane;

DOI:10.1021/ol006477x

Reference yield:

3-isobutoxy-2-(2-propenyl)-2-cyclohexenone (143675-84-7) → Methanesulfonic acid 2-{3-eth-(E)-ylidene-6-[(2-iodo-phenyl)-methanesulfonyl-amino]-cyclohex-1-enyl}-ethyl ester (311309-61-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 72 percent / LDA

2: 83 percent / Et₃N; DMAP / CH₂Cl₂

3: 67 percent / DIBAL-H / CH₂Cl₂

4: 67 percent / NaBH₄; CeCl₃*7H₂O / methanol

5: 51 percent / Me₃P; DIAD; pyridine / tetrahydrofuran

6: 78 percent / OsO₄; NMO / acetone; H₂O; 2-methyl-propan-2-ol

7: 65 percent / NaIO₄ / H₂O; diethyl ether; ethanol

8: 95 percent / NaBH₄ / methanol / 0.33 h

9: 91 percent / DBU / toluene / Heating

10: 78 percent / Et₃N; DMAP / CH₂Cl₂

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; di-isopropyl azodicarboxylate; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; trimethylphosphane; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 1: aldol condensation / 2: Substitution / 3: Reduction / 4: Reduction / 5: Mitsunobu reaction / 6: Oxidation / 7: Oxidation / 8: Reduction / 9: Elimination / 10: Substitution;

DOI:10.1021/ol006477x

Reference yield:

methanesulfonic acid 1-(3-allyl-4-hydroxy-cyclohex-2-enyl)-ethyl ester (311309-55-4) → Methanesulfonic acid 2-{3-eth-(E)-ylidene-6-[(2-iodo-phenyl)-methanesulfonyl-amino]-cyclohex-1-enyl}-ethyl ester (311309-61-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 51 percent / Me₃P; DIAD; pyridine / tetrahydrofuran

2: 78 percent / OsO₄; NMO / acetone; H₂O; 2-methyl-propan-2-ol

3: 65 percent / NaIO₄ / H₂O; diethyl ether; ethanol

4: 95 percent / NaBH₄ / methanol / 0.33 h

5: 91 percent / DBU / toluene / Heating

6: 78 percent / Et₃N; DMAP / CH₂Cl₂

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; di-isopropyl azodicarboxylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trimethylphosphane; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 1: Mitsunobu reaction / 2: Oxidation / 3: Oxidation / 4: Reduction / 5: Elimination / 6: Substitution;

DOI:10.1021/ol006477x

upstream raw materials:

methanesulfonyl chloride

N-[4-ethylidene-2-(2-hydroxy-ethyl)-cyclohex-2-enyl]-N-(2-iodo-phenyl)-methanesulfonamide

3-isobutoxy-2-(2-propenyl)-2-cyclohexenone

methanesulfonic acid 1-(3-allyl-4-oxo-cyclohex-2-enyl)-ethyl ester

Downstream raw materials:

N-[2-(2-azido-ethyl)-4-ethylidene-cyclohex-2-enyl]-N-(2-iodo-phenyl)-methanesulfonamide

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