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

Base Information

• Chemical Name: (+/-)-(2S^*,3R^*,4S^*,5R^*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranyl benzoate
• CAS No.: 98095-66-0
• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.439

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

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

Chemical Property:

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

There total 11 articles about (+/-)-(2S^*,3R^*,4S^*,5R^*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-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: 95.0%

Benzoic acid (2S,3R,4R,5S)-2-((S)-1-iodo-ethyl)-4-(2-methoxy-ethoxymethoxy)-2,4,5-trimethyl-tetrahydro-furan-3-yl ester (98095-65-9,107657-76-1,107657-77-2,110549-58-1,110549-59-2) → (+/-)-(2S*,3R*,4S*,5R*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranyl benzoate (98095-66-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,2-dichloro-benzene; Heating;

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

Reference yield: 87.0%

(+/-)-(2S*,3R*,4R*,5R*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranol (98095-67-1) + benzoyl chloride (98-88-4) → (+/-)-(2S*,3R*,4S*,5R*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranyl benzoate (98095-66-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 48h; Ambient temperature;

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*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranyl benzoate (98095-66-0)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With dmap; lithium borohydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00232a001

upstream raw materials:

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

benzoyl chloride

Benzoic acid (2S,3R,4R,5S)-2-((S)-1-iodo-ethyl)-4-(2-methoxy-ethoxymethoxy)-2,4,5-trimethyl-tetrahydro-furan-3-yl ester

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

Downstream raw materials:

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

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

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