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

Base Information

• Chemical Name: methyl (2E)-3-{(2S,3S)-5-oxo-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-4(E)-tetradecylidene[2-(2,3-dihydrofuryl)]}prop-2-enoate
• CAS No.: 473290-57-2
• Molecular Formula: C₃₇H₅₀O₆
• Molecular Weight: 590.8

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

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

Chemical Property:

Purity/Quality:

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

There total 14 articles about methyl (2E)-3-{(2S,3S)-5-oxo-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-4(E)-tetradecylidene[2-(2,3-dihydrofuryl)]}prop-2-enoate 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: 37.0%

(E)-3-[(2S,3S)-3-Benzyloxy-2-benzyloxymethyl-5-hydroxy-4-tetradec-(Z)-ylidene-tetrahydro-furan-2-yl]-acrylic acid methyl ester → methyl (2E)-3-{(2S,3S)-5-oxo-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-4-tetradecylidene[2-(2,3-dihydrofuryl)]}prop-2-enoate + methyl (2E)-3-{(2S,3S)-5-oxo-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-4(E)-tetradecylidene[2-(2,3-dihydrofuryl)]}prop-2-enoate (473290-57-2) + methyl (2E)-3-{(2S,3S)-5-oxo-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-4(Z)-tetradecylidene[2-(2,3-dihydrofuryl)]}prop-2-enoate (473290-55-0)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 20 ℃;

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) → methyl (2E)-3-{(2S,3S)-5-oxo-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-4(E)-tetradecylidene[2-(2,3-dihydrofuryl)]}prop-2-enoate (473290-57-2)

Guidance literature:

Multi-step reaction with 11 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

9: 31 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

10: 87 percent / aq. HCl / tetrahydrofuran / 0 - 20 °C

11: 37 percent / MnO₂ / CH₂Cl₂ / 20 °C

With hydrogenchloride; dichloro-acetic acid; manganese(IV) oxide; 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 / 9: Wittig reaction;

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

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose (57099-04-4) → methyl (2E)-3-{(2S,3S)-5-oxo-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-4(E)-tetradecylidene[2-(2,3-dihydrofuryl)]}prop-2-enoate (473290-57-2)

Guidance literature:

Multi-step reaction with 12 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

10: 31 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

11: 87 percent / aq. HCl / tetrahydrofuran / 0 - 20 °C

12: 37 percent / MnO₂ / CH₂Cl₂ / 20 °C

With hydrogenchloride; dichloro-acetic acid; manganese(IV) oxide; 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 / 10: Wittig reaction;

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

upstream raw materials:

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

(n-tetradecyl)triphenylphosphonium bromide

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