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

Base Information

• Chemical Name: (+/-)-(2S^*,3S^*,4S^*,5R^*)-2-formyl-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-3-tetrahydrofuranyl benzoate
• CAS No.: 110510-57-1
• Molecular Formula: C₁₉H₂₆O₇
• Molecular Weight: 366.411

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

SDS file from LookChem

Useful:

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

There total 14 articles about (+/-)-(2S^*,3S^*,4S^*,5R^*)-2-formyl-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-3-tetrahydrofuranyl benzoate 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: 70.0%

(+/-)-(2S*,3S*,4S*,5R*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranyl benzoate (98168-77-5) → (+/-)-(2S*,3S*,4S*,5R*)-2-formyl-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-3-tetrahydrofuranyl benzoate (110510-57-1)

Guidance literature:

With 2,3-dimercapto-succinic acid; ozone; In dichloromethane; at -78 ℃;

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

Reference yield:

benzoyl chloride (98-88-4) → (+/-)-(2S*,3S*,4S*,5R*)-2-formyl-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-3-tetrahydrofuranyl benzoate (110510-57-1)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jo00232a001

Reference yield:

Benzoic acid (Z)-(R)-1-[(1R,2S)-2-benzyloxy-1-(2-methoxy-ethoxymethoxy)-1-methyl-propyl]-2-methyl-but-2-enyl ester (107613-13-8) → (+/-)-(2S*,3S*,4S*,5R*)-2-formyl-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-3-tetrahydrofuranyl benzoate (110510-57-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 41 percent / NaHCO₃, I₂ / acetonitrile / 3 h / 0 °C

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

With dimethylsulfide; iodine; sodium hydrogencarbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,2-dichloro-benzene; acetonitrile;

DOI:10.1021/jo00232a001

upstream raw materials:

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

benzoyl chloride

Benzoic acid (Z)-(R)-1-[(1R,2S)-2-benzyloxy-1-(2-methoxy-ethoxymethoxy)-1-methyl-propyl]-2-methyl-but-2-enyl ester

(+/-)-(2R^*,3S^*,4S^*,5R^*)-4-<(2-methoxyethoxy)methoxy>-2-(1-iodoethyl)-2,4,5-trimethyl-3-tetrahydrofuranol

Downstream raw materials:

(+/-)-(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

(+/-)-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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