(E)-3-((2S,3R,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-oxo-tetrahydro-furan-2-yl)-acrylic acid methyl ester

Base Information

• Chemical Name: (E)-3-((2S,3R,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-oxo-tetrahydro-furan-2-yl)-acrylic acid methyl ester
• CAS No.: 473290-51-6
• Molecular Formula: C₂₄H₂₆O₇
• Molecular Weight: 426.466

Synonyms:(E)-3-((2S,3R,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-oxo-tetrahydro-furan-2-yl)-acrylic acid methyl ester

Chemical Property of (E)-3-((2S,3R,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-oxo-tetrahydro-furan-2-yl)-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of (E)-3-((2S,3R,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-oxo-tetrahydro-furan-2-yl)-acrylic acid methyl ester

There total 10 articles about (E)-3-((2S,3R,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-oxo-tetrahydro-furan-2-yl)-acrylic acid methyl ester 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:

(E)-3-((2S,3S,4R,5R)-3-Benzyloxy-2-benzyloxymethyl-4-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-acrylic acid methyl ester (473290-50-5) → (E)-3-((2S,3R,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-oxo-tetrahydro-furan-2-yl)-acrylic acid methyl ester (473290-51-6)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4020(02)00477-5

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose (63593-02-2) → (E)-3-((2S,3R,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-oxo-tetrahydro-furan-2-yl)-acrylic acid methyl ester (473290-51-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / aq. NaOH / dioxane

2: 38 percent / n-BuLi / hexane; tetrahydrofuran / 1 h / Heating

3: 76 percent / NaH; n-Bu₄NI / tetrahydrofuran / 3 h / 20 °C

4: 93 percent / n-Bu₄NF / tetrahydrofuran / 20 °C

5: dicyclohexylcarbodiimide; dichloroacetic acid / dimethylsulfoxide / 20 °C

6: 1.05 g / CH₂Cl₂ / 20 °C

7: 52 percent / HCl / 0.5 h / 85 °C

8: (COCl)2; DMSO; Et₃N / CH₂Cl₂

With hydrogenchloride; dichloro-acetic acid; sodium hydroxide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; dimethyl sulfoxide; 1: Cannizzaro reaction / 6: Wittig reaction / 8: Swern oxidation;

DOI:10.1016/S0040-4020(02)00477-5

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose (57099-04-4) → (E)-3-((2S,3R,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-oxo-tetrahydro-furan-2-yl)-acrylic acid methyl ester (473290-51-6)

Guidance literature:

Multi-step reaction with 9 steps

1: aq. NaIO₄ / methanol

2: 94 percent / aq. NaOH / dioxane

3: 38 percent / n-BuLi / hexane; tetrahydrofuran / 1 h / Heating

4: 76 percent / NaH; n-Bu₄NI / tetrahydrofuran / 3 h / 20 °C

5: 93 percent / n-Bu₄NF / tetrahydrofuran / 20 °C

6: dicyclohexylcarbodiimide; dichloroacetic acid / dimethylsulfoxide / 20 °C

7: 1.05 g / CH₂Cl₂ / 20 °C

8: 52 percent / HCl / 0.5 h / 85 °C

9: (COCl)2; DMSO; Et₃N / CH₂Cl₂

With hydrogenchloride; dichloro-acetic acid; sodium hydroxide; sodium periodate; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; dimethyl sulfoxide; 2: Cannizzaro reaction / 7: Wittig reaction / 9: Swern oxidation;

DOI:10.1016/S0040-4020(02)00477-5

upstream raw materials:

(E)-3-((2S,3S,4R,5R)-3-Benzyloxy-2-benzyloxymethyl-4-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-acrylic acid methyl ester

3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose

1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose

Downstream raw materials:

methyl (2E)-3-{(2S,3S)-5-oxo-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-4(E)-tetradecylidene[2-(2,3-dihydrofuryl)]}prop-2-enoate

methyl (2E)-3-{(2S,3S)-5-oxo-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-4(Z)-tetradecylidene[2-(2,3-dihydrofuryl)]}prop-2-enoate

(E)-3-[(2S,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-tetradec-(Z)-ylidene-tetrahydro-furan-2-yl]-acrylic acid methyl ester

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