Benzoic acid (E)-(R)-1-((E)-2-methoxycarbonyl-vinyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

Base Information

• Chemical Name: Benzoic acid (E)-(R)-1-((E)-2-methoxycarbonyl-vinyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester
• CAS No.: 153896-19-6
• Molecular Formula: C₂₁H₂₆O₆
• Molecular Weight: 374.434
• Mol file: 153896-19-6.mol

Synonyms:Benzoic acid (E)-(R)-1-((E)-2-methoxycarbonyl-vinyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

Chemical Property of Benzoic acid (E)-(R)-1-((E)-2-methoxycarbonyl-vinyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (E)-(R)-1-((E)-2-methoxycarbonyl-vinyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

There total 13 articles about Benzoic acid (E)-(R)-1-((E)-2-methoxycarbonyl-vinyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl 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: 88.0%

trimethyl phosphonoacetate (5927-18-4) + Benzoic acid (E)-(R)-1-formyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester (1026718-20-6) → Benzoic acid (E)-(R)-1-((E)-2-methoxycarbonyl-vinyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester (153896-19-6)

Guidance literature:

With sodium hydride; In benzene; at 0 ℃; for 0.5h;

DOI:10.1021/jo9619241

Reference yield:

trans-1-methanesulfonyloxy-4-(tetrahydropyran-2-yloxy)-2-butene (119343-28-1) → Benzoic acid (E)-(R)-1-((E)-2-methoxycarbonyl-vinyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester (153896-19-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / LiBr / dimethylformamide / 27 h / 0 °C

2: 75 percent / copper(I) chloride / tetrahydrofuran / 12 h / Ambient temperature

3: 81 percent / LiAlH₄ / tetrahydrofuran / 4 h / -78 °C

4: 80 percent / Ti(OPr-i)4, (R,R)-(+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

5: 84 percent / Ti(OPr-i)4 / CH₂Cl₂ / 0.25 h / Ambient temperature

6: NaIO₄ / tetrahydrofuran; H₂O / 2 h / Ambient temperature

7: 88 percent / NaH / benzene / 0.5 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; sodium hydride; copper(l) chloride; lithium bromide; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo9619241

Reference yield:

(E)-2-((4-bromobut-2-en-1-yl)oxy)tetrahydro-2H-pyran (98234-53-8,119343-29-2) → Benzoic acid (E)-(R)-1-((E)-2-methoxycarbonyl-vinyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester (153896-19-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / copper(I) chloride / tetrahydrofuran / 12 h / Ambient temperature

2: 81 percent / LiAlH₄ / tetrahydrofuran / 4 h / -78 °C

3: 80 percent / Ti(OPr-i)4, (R,R)-(+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

4: 84 percent / Ti(OPr-i)4 / CH₂Cl₂ / 0.25 h / Ambient temperature

5: NaIO₄ / tetrahydrofuran; H₂O / 2 h / Ambient temperature

6: 88 percent / NaH / benzene / 0.5 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; sodium hydride; copper(l) chloride; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; water; benzene;

DOI:10.1021/jo9619241

upstream raw materials:

trimethylphosphonoacetate anion

Benzoic acid (E)-(R)-1-((S)-1,2-dihydroxy-ethyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

methyl (triphenylphosphoranylidene)acetate

trimethyl phosphonoacetate

Downstream raw materials:

Benzoic acid (E)-(R)-5-hydroxy-1-((E)-2-methoxycarbonyl-vinyl)-pent-3-enyl ester

(1R)-1-[(2R,3S)-2-(benzoyloxy)-3,4-dihydroxybutyl]-3-(methoxycarbonyl)-2(E)-allyl benzoate