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

Base Information

• Chemical Name: (+/-)-(2S^*,3S^*,4S^*,5R^*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran
• CAS No.: 110510-59-3
• Molecular Formula: C₂₄H₃₄O₈
• Molecular Weight: 450.529

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

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

Chemical Property:

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

There total 15 articles about (+/-)-(2S^*,3S^*,4S^*,5R^*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran 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: 97.0%

(+/-)-(2S*,3S*,4S*,5R*)-2-formyl-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-3-tetrahydrofuranyl benzoate (110510-57-1) + (carbethoxyethylidene)triphenylphosphorane (21382-82-1) → (+/-)-(2S*,3S*,4S*,5R*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran (110510-59-3)

Guidance literature:

In dichloromethane;

DOI:10.1016/S0040-4039(00)98828-2

Reference yield:

(+/-)-(2S*,3S*,4S*,5R*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranyl benzoate (98168-77-5) → (+/-)-(2S*,3S*,4S*,5R*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran (110510-59-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 93 percent / benzene / 72 h / Heating

With dimethylsulfide; ozone; In benzene;

DOI:10.1021/jo00232a001

Reference yield:

benzoyl chloride (98-88-4) → (+/-)-(2S*,3S*,4S*,5R*)-3-(benzoyloxy)-2-<2-carbethoxy-1(E)-propenyl>-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran (110510-59-3)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N, 4-DMAP / CH₂Cl₂ / Ambient temperature

2: 93 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / 1,2-dichloro-benzene / 0.33 h / 180 °C

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

4: 93 percent / benzene / 72 h / Heating

With dmap; dimethylsulfide; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; 1,2-dichloro-benzene; benzene;

DOI:10.1021/jo00232a001

upstream raw materials:

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

(carbethoxyethylidene)triphenylphosphorane

benzoyl chloride

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

Downstream raw materials:

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

(+/-)-citreoviral

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

(+/-)-epicitreoviral

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