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

Base Information

• Chemical Name: (2R^*,3R^*,5S^*,6R^*)-2-<(benzyloxy)methyl>-6-ethenyl-3,5-dimethyl-3,4,5,6-tetrahydropyran-2-ol
• CAS No.: 98944-67-3
• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.376

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

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

Chemical Property:

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

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

(3S,5R,6R)-3,5-Dimethyl-6-(1-phenylselanyl-ethyl)-tetrahydro-pyran-2-one (98944-65-1) → (2R*,3R*,5S*,6R*)-2-<(benzyloxy)methyl>-6-ethenyl-3,5-dimethyl-3,4,5,6-tetrahydropyran-2-ol (98944-67-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / chloramine-T, triethylbenzylammonium chloride / benzene / 3 h / 21 °C / pH 7.5

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

With n-butyllithium; N-benzyl-N,N,N-triethylammonium chloride; chloroamine-T; In benzene;

DOI:10.1021/jo00225a040

Reference yield:

(benzyloxymethyl)tributylstannane (66222-28-4) + (3R*,5S*,6R*)-6-ethenyl-3,5-dimethyl-3,4,5,6-tetrahydro-2-pyrone (98944-66-2) → (2R*,3R*,5S*,6R*)-2-<(benzyloxy)methyl>-6-ethenyl-3,5-dimethyl-3,4,5,6-tetrahydropyran-2-ol (98944-67-3)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, hexane, -78 deg C, 4 min, 2.) THF, hexane, 5 min;

DOI:10.1021/jo00225a040

Reference yield: 92.0%

propionic acid anhydride (123-62-6) + (2R*,3R*,5S*,6R*)-2-<(benzyloxy)methyl>-6-ethenyl-3,5-dimethyl-3,4,5,6-tetrahydropyran-2-ol (98944-67-3) → Propionic acid (1S,2R,4S)-6-benzyloxy-2,4-dimethyl-5-oxo-1-vinyl-hexyl ester

Guidance literature:

With dmap; at 21 ℃; for 0.5h;

DOI:10.1021/jo00225a040

upstream raw materials:

(benzyloxymethyl)tributylstannane

(3R^*,5S^*,6R^*)-6-ethenyl-3,5-dimethyl-3,4,5,6-tetrahydro-2-pyrone

(3S,5R,6R)-3,5-Dimethyl-6-(1-phenylselanyl-ethyl)-tetrahydro-pyran-2-one

Downstream raw materials:

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

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

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