5-<(2R^*,4S^*)-1-iodo-5,5-(ethylenedioxy)-2,4-dimethyl-6-(phenylmethoxy)hexyl>-3-methyl-4,5-dihydro-2(3H)-furanone

Base Information

• Chemical Name: 5-<(2R^*,4S^*)-1-iodo-5,5-(ethylenedioxy)-2,4-dimethyl-6-(phenylmethoxy)hexyl>-3-methyl-4,5-dihydro-2(3H)-furanone
• CAS No.: 98944-72-0
• Molecular Formula: C₂₂H₃₁IO₅
• Molecular Weight: 502.39

Synonyms:5-<(2R^*,4S^*)-1-iodo-5,5-(ethylenedioxy)-2,4-dimethyl-6-(phenylmethoxy)hexyl>-3-methyl-4,5-dihydro-2(3H)-furanone

Chemical Property of 5-<(2R^*,4S^*)-1-iodo-5,5-(ethylenedioxy)-2,4-dimethyl-6-(phenylmethoxy)hexyl>-3-methyl-4,5-dihydro-2(3H)-furanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-<(2R^*,4S^*)-1-iodo-5,5-(ethylenedioxy)-2,4-dimethyl-6-(phenylmethoxy)hexyl>-3-methyl-4,5-dihydro-2(3H)-furanone

There total 6 articles about 5-<(2R^*,4S^*)-1-iodo-5,5-(ethylenedioxy)-2,4-dimethyl-6-(phenylmethoxy)hexyl>-3-methyl-4,5-dihydro-2(3H)-furanone 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:

methyl (2R*,4E,6R*,8S*)-9,9-(ethylenedioxy)-2,6,8-trimethyl-10-(phenylmethoxy)-4-decenoate (98944-70-8) → 5-<(2R*,4S*)-1-iodo-5,5-(ethylenedioxy)-2,4-dimethyl-6-(phenylmethoxy)hexyl>-3-methyl-4,5-dihydro-2(3H)-furanone (98944-72-0)

Guidance literature:

With iodine; In acetonitrile; at -15 ℃; for 9h;

DOI:10.1021/jo00225a040

Reference yield:

(benzyloxymethyl)tributylstannane (66222-28-4) → 5-<(2R*,4S*)-1-iodo-5,5-(ethylenedioxy)-2,4-dimethyl-6-(phenylmethoxy)hexyl>-3-methyl-4,5-dihydro-2(3H)-furanone (98944-72-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) butyllithium / 1.) THF, hexane, -78 deg C, 4 min, 2.) THF, hexane, 5 min

2: 92 percent / 4-(dimethylamino)pyridine / 0.5 h / 21 °C

3: 94 percent / trimethylsilyl triflate / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) from -78 deg C to 0 deg C, 6 h

4: 1.) LDA, HMPA, 2.) tert-butyldimethylsilyl chloride / 1.) THF, hexane, -75 deg C, 7 min, 2.) THF, hexane, a) -78 deg C, 9 min, b) 21 deg C, 2.5 h

5: 91 percent / diethyl ether / 0.33 h / 0 °C

6: I₂ / acetonitrile / 9 h / -15 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; iodine; tert-butyldimethylsilyl chloride; lithium diisopropyl amide; In diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/jo00225a040

Reference yield:

(2R*,3R*,5S*,6R*)-2-<(benzyloxy)methyl>-6-ethenyl-3,5-dimethyl-3,4,5,6-tetrahydropyran-2-ol (98944-67-3) → 5-<(2R*,4S*)-1-iodo-5,5-(ethylenedioxy)-2,4-dimethyl-6-(phenylmethoxy)hexyl>-3-methyl-4,5-dihydro-2(3H)-furanone (98944-72-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / 4-(dimethylamino)pyridine / 0.5 h / 21 °C

2: 94 percent / trimethylsilyl triflate / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) from -78 deg C to 0 deg C, 6 h

3: 1.) LDA, HMPA, 2.) tert-butyldimethylsilyl chloride / 1.) THF, hexane, -75 deg C, 7 min, 2.) THF, hexane, a) -78 deg C, 9 min, b) 21 deg C, 2.5 h

4: 91 percent / diethyl ether / 0.33 h / 0 °C

5: I₂ / acetonitrile / 9 h / -15 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; trimethylsilyl trifluoromethanesulfonate; iodine; tert-butyldimethylsilyl chloride; lithium diisopropyl amide; In diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/jo00225a040

upstream raw materials:

methyl (2R^*,4E,6R^*,8S^*)-9,9-(ethylenedioxy)-2,6,8-trimethyl-10-(phenylmethoxy)-4-decenoate

(benzyloxymethyl)tributylstannane

(2R^*,3R^*,5S^*,6R^*)-2-<(benzyloxy)methyl>-6-ethenyl-3,5-dimethyl-3,4,5,6-tetrahydropyran-2-ol

(1R^*,2S^*,4R^*)-1-ethenyl-5,5-(ethylenedioxy)-2,4-dimethyl-6-(phenylmethoxy)hexyl propanoate

Downstream raw materials:

5-<(2R^*,4S^*)-5,5-(ethylenedioxy)-1-hydroxy-2,4-dimethyl-6-(phenylmethoxy)hexyl>-3-methyl-4,5-dihydro-2(3H)-furanone

(3R^*,5S^*)-5-<(2R^*,3R^*,5S^*,6R^*)-6-hydroxy-3,5-dimethyl-6-(phenylmethoxy)-2,3,4,5-tetrahydropyran-2-yl>-3-methyl-4,5-dihydro-2(3H)-furanone

(3R^*,5S^*)-5-<(2R^*,3R^*,5S^*,6S^*)-6-hydroxy-3,5-dimethyl-6-(phenylmethoxy)-2,3,4,5-tetrahydropyran-2-yl>-3-methyl-4,5-dihydro-2(3H)-furanone

methyl (6R^*,8S^*)-4,5-epoxy-9,9-(ethylenedioxy)-2,6,8-trimethyl-10-(phenylmethoxy)decanoate

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