(+/-)-(2S^*,3R^*,4S^*,5R^*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran-4-ol

Base Information

• Chemical Name: (+/-)-(2S^*,3R^*,4S^*,5R^*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran-4-ol
• CAS No.: 110510-62-8
• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.423

Synonyms:(+/-)-(2S^*,3R^*,4S^*,5R^*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran-4-ol

Chemical Property of (+/-)-(2S^*,3R^*,4S^*,5R^*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran-4-ol

Chemical Property:

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Technology Process of (+/-)-(2S^*,3R^*,4S^*,5R^*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran-4-ol

There total 7 articles about (+/-)-(2S^*,3R^*,4S^*,5R^*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran-4-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: 86.0%

(+/-)-(2S*,3R*,4S*,5R*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran (110510-60-6) → (+/-)-(2S*,3R*,4S*,5R*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran-4-ol (110510-62-8)

Guidance literature:

With zinc dibromide; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1021/jo00232a001

Reference yield:

(+/-)-(2S*,3R*,4R*,5R*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranol (98095-67-1) → (+/-)-(2S*,3R*,4S*,5R*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran-4-ol (110510-62-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h / Ambient temperature

2: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, from -78 deg C to 22 deg C

3: 98 percent / benzene / 36 h / Heating

4: 86 percent / ZnBr₂ / CH₂Cl₂ / 2 h / Ambient temperature

With dmap; dimethylsulfide; ozone; triethylamine; zinc dibromide; In dichloromethane; benzene;

DOI:10.1021/jo00232a001

Reference yield:

(+/-)-(2S*,4S*,5R*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranone (98095-68-2) → (+/-)-(2S*,3R*,4S*,5R*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran-4-ol (110510-62-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / LiBH₄ / tetrahydrofuran / 1 h / 0 °C

2: 87 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h / Ambient temperature

3: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, from -78 deg C to 22 deg C

4: 98 percent / benzene / 36 h / Heating

5: 86 percent / ZnBr₂ / CH₂Cl₂ / 2 h / Ambient temperature

With dmap; lithium borohydride; dimethylsulfide; ozone; triethylamine; zinc dibromide; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/jo00232a001

upstream raw materials:

(+/-)-(2S^*,3R^*,4S^*,5R^*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran

(+/-)-(2S^*,3R^*,4R^*,5R^*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranol

(+/-)-(2S^*,4S^*,5R^*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranone

(+/-)-(2S^*,3R^*,4S^*,5R^*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranyl benzoate

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