2-((E)-(4S,5S,6R)-7-Hydroxy-4,5,6-tris-methoxymethoxy-hept-1-enyl)-4-methoxy-6-methoxymethoxy-benzoic acid methyl ester

Base Information

Chemical Name:2-((E)-(4S,5S,6R)-7-Hydroxy-4,5,6-tris-methoxymethoxy-hept-1-enyl)-4-methoxy-6-methoxymethoxy-benzoic acid methyl ester
CAS No.:335058-78-1
Molecular Formula:C₂₄H₃₈O₁₂
Molecular Weight:518.559
Hs Code.:

Synonyms:

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Chemical Property of 2-((E)-(4S,5S,6R)-7-Hydroxy-4,5,6-tris-methoxymethoxy-hept-1-enyl)-4-methoxy-6-methoxymethoxy-benzoic acid methyl ester

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Technology Process of 2-((E)-(4S,5S,6R)-7-Hydroxy-4,5,6-tris-methoxymethoxy-hept-1-enyl)-4-methoxy-6-methoxymethoxy-benzoic acid methyl ester

There total 10 articles about 2-((E)-(4S,5S,6R)-7-Hydroxy-4,5,6-tris-methoxymethoxy-hept-1-enyl)-4-methoxy-6-methoxymethoxy-benzoic 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:

: 335058-46-3
Benzyl-β-D-ribopyranosid

: 335058-78-1
2-((E)-(4S,5S,6R)-7-Hydroxy-4,5,6-tris-methoxymethoxy-hept-1-enyl)-4-methoxy-6-methoxymethoxy-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 85 percent / i-Pr₂NEt / acetonitrile / 4 h / 50 °C

2: 100 percent / H₂ / Pd(OH)2 / ethanol / 3 h

3: n-BuLi; BF₃*Et₂O / tetrahydrofuran / -78 - 20 °C

4: pyridine / 1 h / 0 °C

5: 100 percent / TBAF / acetic acid; tetrahydrofuran / 2 h

6: 85 percent / CuI; Ph₃P; Et₃N / Pd(OAc)2 / 2 h

7: 98 percent / pyridine / 1 h / 0 °C

8: H₂ / Pd/BaCO₃ / ethanol; quinoline / 0.5 h

9: n-Bu₃P / Pd₂(dba)3CHCl₃ / dioxane; formamide / 1 h / 95 °C

10: 95 percent / NaOMe / methanol / 3 h / 50 °C

With copper(l) iodide; n-butyllithium; tributylphosphine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium diacetate; palladium dihydroxide; palladium-barium carbonate; In tetrahydrofuran; 1,4-dioxane; pyridine; quinoline; methanol; ethanol; formamide; acetic acid; acetonitrile; 6: Sonogashira coupling / 9: Tsuji hydrogenolysis;
DOI:10.1246/cl.2001.172

Reference yield:

: 10257-32-6
D-ribose

: 335058-78-1
2-((E)-(4S,5S,6R)-7-Hydroxy-4,5,6-tris-methoxymethoxy-hept-1-enyl)-4-methoxy-6-methoxymethoxy-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 89 percent / CSA / 80 °C

2: 85 percent / i-Pr₂NEt / acetonitrile / 4 h / 50 °C

3: 100 percent / H₂ / Pd(OH)2 / ethanol / 3 h

4: n-BuLi; BF₃*Et₂O / tetrahydrofuran / -78 - 20 °C

5: pyridine / 1 h / 0 °C

6: 100 percent / TBAF / acetic acid; tetrahydrofuran / 2 h

7: 85 percent / CuI; Ph₃P; Et₃N / Pd(OAc)2 / 2 h

8: 98 percent / pyridine / 1 h / 0 °C

9: H₂ / Pd/BaCO₃ / ethanol; quinoline / 0.5 h

10: n-Bu₃P / Pd₂(dba)3CHCl₃ / dioxane; formamide / 1 h / 95 °C

11: 95 percent / NaOMe / methanol / 3 h / 50 °C

With copper(l) iodide; n-butyllithium; tributylphosphine; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium diacetate; palladium dihydroxide; palladium-barium carbonate; In tetrahydrofuran; 1,4-dioxane; pyridine; quinoline; methanol; ethanol; formamide; acetic acid; acetonitrile; 7: Sonogashira coupling / 10: Tsuji hydrogenolysis;
DOI:10.1246/cl.2001.172

Reference yield:

: (3R,4R,5R)-3,4,5-Tris-methoxymethoxy-tetrahydro-pyran-2-ol

: 335058-78-1
2-((E)-(4S,5S,6R)-7-Hydroxy-4,5,6-tris-methoxymethoxy-hept-1-enyl)-4-methoxy-6-methoxymethoxy-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: n-BuLi; BF₃*Et₂O / tetrahydrofuran / -78 - 20 °C

2: pyridine / 1 h / 0 °C

3: 100 percent / TBAF / acetic acid; tetrahydrofuran / 2 h

4: 85 percent / CuI; Ph₃P; Et₃N / Pd(OAc)2 / 2 h

5: 98 percent / pyridine / 1 h / 0 °C

6: H₂ / Pd/BaCO₃ / ethanol; quinoline / 0.5 h

7: n-Bu₃P / Pd₂(dba)3CHCl₃ / dioxane; formamide / 1 h / 95 °C

8: 95 percent / NaOMe / methanol / 3 h / 50 °C

With copper(l) iodide; n-butyllithium; tributylphosphine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; triethylamine; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium diacetate; palladium-barium carbonate; In tetrahydrofuran; 1,4-dioxane; pyridine; quinoline; methanol; ethanol; formamide; acetic acid; 4: Sonogashira coupling / 7: Tsuji hydrogenolysis;
DOI:10.1246/cl.2001.172