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

Base Information

• Chemical Name: (E)-3-[(2S,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-tetradec-(Z)-ylidene-tetrahydro-furan-2-yl]-acrylic acid methyl ester
• CAS No.: 473290-53-8
• Molecular Formula: C₃₈H₅₄O₆
• Molecular Weight: 606.843

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

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

There total 11 articles about (E)-3-[(2S,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-tetradec-(Z)-ylidene-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: 31.0%

(n-tetradecyl)triphenylphosphonium bromide (25791-20-2) + (E)-3-((2S,3R,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-oxo-tetrahydro-furan-2-yl)-acrylic acid methyl ester (473290-51-6) → (E)-3-[(2S,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-tetradec-(Z)-ylidene-tetrahydro-furan-2-yl]-acrylic acid methyl ester (473290-53-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 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) → (E)-3-[(2S,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-tetradec-(Z)-ylidene-tetrahydro-furan-2-yl]-acrylic acid methyl ester (473290-53-8)

Guidance literature:

Multi-step reaction with 9 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

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 / 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) → (E)-3-[(2S,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-tetradec-(Z)-ylidene-tetrahydro-furan-2-yl]-acrylic acid methyl ester (473290-53-8)

Guidance literature:

Multi-step reaction with 10 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

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 / 10: Wittig reaction;

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

upstream raw materials:

(n-tetradecyl)triphenylphosphonium bromide

(E)-3-((2S,3R,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-oxo-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

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

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