(3S,4R)-4-(Benzo[1,3]dioxole-5-carbonyl)-3-[(S)-hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one

Base Information

• Chemical Name: (3S,4R)-4-(Benzo[1,3]dioxole-5-carbonyl)-3-[(S)-hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one
• CAS No.: 135965-93-4
• Molecular Formula: C₂₂H₂₂O₉
• Molecular Weight: 430.411

Synonyms:(3S,4R)-4-(Benzo[1,3]dioxole-5-carbonyl)-3-[(S)-hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one

Chemical Property of (3S,4R)-4-(Benzo[1,3]dioxole-5-carbonyl)-3-[(S)-hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one

Chemical Property:

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Technology Process of (3S,4R)-4-(Benzo[1,3]dioxole-5-carbonyl)-3-[(S)-hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one

There total 4 articles about (3S,4R)-4-(Benzo[1,3]dioxole-5-carbonyl)-3-[(S)-hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one 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: 83.0%

(3S,4R)-4-(2-Benzo[1,3]dioxol-5-yl-[1,3]dithian-2-yl)-3-[(S)-hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one (136031-31-7) → (3S,4R)-4-(Benzo[1,3]dioxole-5-carbonyl)-3-[(S)-hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one (135965-93-4)

Guidance literature:

With calcium carbonate; mercury dichloride; In water; acetone; acetonitrile; at 85 ℃; for 12h;

DOI:10.1016/S0040-4020(01)86473-5

Reference yield:

2-(3,4-methylenedioxyphenyl)-1,3-dithiane (56579-86-3) → (3S,4R)-4-(Benzo[1,3]dioxole-5-carbonyl)-3-[(S)-hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one (135965-93-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n.butyllithium / 1.) THF, hexane, -78 deg C, 1 h 2.) THF, -84 deg C, 2 h

2: 81 percent / NaBH₄, KOH / ethanol / 1.5 h / Ambient temperature

4: 83 percent / HgCl₂, CaCO₃ / acetonitrile; acetone; H₂O / 12 h / 85 °C

With potassium hydroxide; sodium tetrahydroborate; n-butyllithium; calcium carbonate; mercury dichloride; In ethanol; water; acetone; acetonitrile;

DOI:10.1016/S0040-4020(01)86473-5

Reference yield:

(3R)-3-[(propane-1,3-diyldithio)-(3,4-methylenedioxyphenyl)methyl]butano-4-lactone (136031-30-6) → (3S,4R)-4-(Benzo[1,3]dioxole-5-carbonyl)-3-[(S)-hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one (135965-93-4)

Guidance literature:

Multi-step reaction with 2 steps

2: 83 percent / HgCl₂, CaCO₃ / acetonitrile; acetone; H₂O / 12 h / 85 °C

With calcium carbonate; mercury dichloride; In water; acetone; acetonitrile;

DOI:10.1016/S0040-4020(01)86473-5

upstream raw materials:

(3S,4R)-4-(2-Benzo[1,3]dioxol-5-yl-[1,3]dithian-2-yl)-3-[(S)-hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one

2-(3,4-methylenedioxyphenyl)-1,3-dithiane

(3R)-3-[(propane-1,3-diyldithio)-(3,4-methylenedioxyphenyl)methyl]butano-4-lactone

(3R,4R)-3-[(propane-1,3-diyldithio)-(3,4-methylenedioxyphenyl)methyl]-4-[(1R,2S,5R)-2-(1-methylethyl)-5-methyl-1-cyclohexyloxy]butano-4-lactone

Downstream raw materials:

(3S,4R)-4-((S)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-3-[(S)-(1-ethoxy-ethoxy)-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one

(4aR,5R,6R,11bS)-2,2-Di-tert-butyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-2-sila-cyclopenta[b]phenanthrene-5-carboxylic acid methyl ester

(2S,3S)-2-((4S,5R)-4-Benzo[1,3]dioxol-5-yl-2,2-di-tert-butyl-[1,3,2]dioxasilinan-5-yl)-3-hydroxy-3-(3,4,5-trimethoxy-phenyl)-propionic acid methyl ester

(2S,3S)-2-((4S,5R)-4-Benzo[1,3]dioxol-5-yl-2,2-di-tert-butyl-[1,3,2]dioxasilinan-5-yl)-3-(1-ethoxy-ethoxy)-3-(3,4,5-trimethoxy-phenyl)-propionic acid methyl ester

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