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

Base Information

• Chemical Name: (1R^*,2S^*,4R^*)-1-ethenyl-5,5-(ethylenedioxy)-2,4-dimethyl-6-(phenylmethoxy)hexyl propanoate
• CAS No.: 98944-68-4
• Molecular Formula: C₂₂H₃₂O₅
• Molecular Weight: 376.493

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 3 articles about (1R^*,2S^*,4R^*)-1-ethenyl-5,5-(ethylenedioxy)-2,4-dimethyl-6-(phenylmethoxy)hexyl propanoate 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%

2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane (7381-30-8) + Propionic acid (1S,2R,4S)-6-benzyloxy-2,4-dimethyl-5-oxo-1-vinyl-hexyl ester → (1R*,2S*,4R*)-1-ethenyl-5,5-(ethylenedioxy)-2,4-dimethyl-6-(phenylmethoxy)hexyl propanoate (98944-68-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; 1.) -78 deg C, 1 h, 2.) from -78 deg C to 0 deg C, 6 h;

DOI:10.1021/jo00225a040

Reference yield:

(benzyloxymethyl)tributylstannane (66222-28-4) → (1R*,2S*,4R*)-1-ethenyl-5,5-(ethylenedioxy)-2,4-dimethyl-6-(phenylmethoxy)hexyl propanoate (98944-68-4)

Guidance literature:

Multi-step reaction with 3 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

With dmap; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

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) → (1R*,2S*,4R*)-1-ethenyl-5,5-(ethylenedioxy)-2,4-dimethyl-6-(phenylmethoxy)hexyl propanoate (98944-68-4)

Guidance literature:

Multi-step reaction with 2 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

With dmap; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1021/jo00225a040

upstream raw materials:

2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane

(benzyloxymethyl)tributylstannane

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

Downstream raw materials:

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

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

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

(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

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