(3R,5R)-5-((1S)-1-hydroxyethyl)-2-methoxyoxolan-3-yl 6-methoxy-2-prop-2-enylbenzoate

Base Information

• Chemical Name: (3R,5R)-5-((1S)-1-hydroxyethyl)-2-methoxyoxolan-3-yl 6-methoxy-2-prop-2-enylbenzoate
• CAS No.: 620987-55-5
• Molecular Formula: C₁₈H₂₄O₆
• Molecular Weight: 336.385
• Mol file: 620987-55-5.mol

Synonyms:(3R,5R)-5-((1S)-1-hydroxyethyl)-2-methoxyoxolan-3-yl 6-methoxy-2-prop-2-enylbenzoate

Chemical Property of (3R,5R)-5-((1S)-1-hydroxyethyl)-2-methoxyoxolan-3-yl 6-methoxy-2-prop-2-enylbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R)-5-((1S)-1-hydroxyethyl)-2-methoxyoxolan-3-yl 6-methoxy-2-prop-2-enylbenzoate

There total 13 articles about (3R,5R)-5-((1S)-1-hydroxyethyl)-2-methoxyoxolan-3-yl 6-methoxy-2-prop-2-enylbenzoate 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: 74.0%

methanol (67-56-1) + (3R,5R)-5-((1S)-1-hydroxyethyl)-2-oxo-3,4,5-trihydrofuryl 6-methoxy-2-prop-2-enylbenzoate (620987-54-4) → (3R,5R)-5-((1S)-1-hydroxyethyl)-2-methoxyoxolan-3-yl 6-methoxy-2-prop-2-enylbenzoate (620987-55-5)

Guidance literature:

(3R,5R)-5-((1S)-1-hydroxyethyl)-2-oxo-3,4,5-trihydrofuryl 6-methoxy-2-prop-2-enylbenzoate; With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.25h;

methanol; With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 8h;

DOI:10.1021/jo050750x

Reference yield:

L-rhamnose (73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6) → (3R,5R)-5-((1S)-1-hydroxyethyl)-2-methoxyoxolan-3-yl 6-methoxy-2-prop-2-enylbenzoate (620987-55-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 99 percent / BaCO₃; Br₂ / H₂O / 24 h / 20 °C

2.1: 99 percent / pyridine / 0 - 20 °C

3.1: 99 percent / H₂; Et₃N / Pd/C / ethyl acetate / 24 h / 20 °C / 2585.74 Torr

4.1: NaOMe / methanol / 3 h / 20 °C

4.2: 87 percent / H₂SO₄ / dioxane / 1 h / 20 °C

5.1: 90 percent / EDCI; DMAP / CH₂Cl₂ / 24 h / 20 °C

6.1: DIBAL-H / toluene / 0.25 h / -78 °C

7.1: HCl / dioxane / 4 h / 20 °C

With pyridine; hydrogenchloride; dmap; hydrogen; bromine; sodium methylate; diisobutylaluminium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; barium carbonate; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/ol035630v

Reference yield:

2,3,5-tri-O-benzoyl-L-rhamnono-1,4-lactone (81644-86-2) → (3R,5R)-5-((1S)-1-hydroxyethyl)-2-methoxyoxolan-3-yl 6-methoxy-2-prop-2-enylbenzoate (620987-55-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 99 percent / H₂; Et₃N / Pd/C / ethyl acetate / 24 h / 20 °C / 2585.74 Torr

2.1: NaOMe / methanol / 3 h / 20 °C

2.2: 87 percent / H₂SO₄ / dioxane / 1 h / 20 °C

3.1: 90 percent / EDCI; DMAP / CH₂Cl₂ / 24 h / 20 °C

4.1: DIBAL-H / toluene / 0.25 h / -78 °C

5.1: HCl / dioxane / 4 h / 20 °C

With hydrogenchloride; dmap; hydrogen; sodium methylate; diisobutylaluminium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/ol035630v

upstream raw materials:

methanol

(3R,5R)-5-((1S)-1-hydroxyethyl)-2-oxo-3,4,5-trihydrofuryl 6-methoxy-2-prop-2-enylbenzoate

L-rhamnose

(3R,4R,5R,6S)-6-methyl-2-oxo-4,5-diphenylcarbonyloxy-3H-4,5,6-trihydropyran-3-yl benzoate

Downstream raw materials:

2-Allyl-6-methoxy-benzoic acid (3R,5R)-2-methoxy-5-((S)-1-trifluoromethanesulfonyloxy-ethyl)-tetrahydro-furan-3-yl ester

(3R,5R)-5-((1S)-1-methylbut-3-enyl)-2-methoxyoxolan-3-yl 6-methoxy-2-prop-2-enylbenzoate

(3R,5R)-5-((1S)-1-methylbut-3-enyl)-2-hydroxyoxolan-3-yl 6-hydroxy-2-prop-2-enylbenzoate

1-((1E)-2-cyanovinyl)-(1R,3R,4S)-3-hydroxy-4-methylhept-6-enyl 6-hydroxy-2-prop-2-enylbenzoate