Benzoic acid (R)-1-((E)-2-methoxycarbonyl-vinyl)-4-(tetrahydro-pyran-2-yloxy)-butyl ester

Base Information

Chemical Name:Benzoic acid (R)-1-((E)-2-methoxycarbonyl-vinyl)-4-(tetrahydro-pyran-2-yloxy)-butyl ester
CAS No.:128778-20-1
Molecular Formula:C₂₀H₂₆O₆
Molecular Weight:362.423
Hs Code.:

Synonyms:Benzoic acid (R)-1-((E)-2-methoxycarbonyl-vinyl)-4-(tetrahydro-pyran-2-yloxy)-butyl ester

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Chemical Property of Benzoic acid (R)-1-((E)-2-methoxycarbonyl-vinyl)-4-(tetrahydro-pyran-2-yloxy)-butyl ester

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Technology Process of Benzoic acid (R)-1-((E)-2-methoxycarbonyl-vinyl)-4-(tetrahydro-pyran-2-yloxy)-butyl ester

There total 10 articles about Benzoic acid (R)-1-((E)-2-methoxycarbonyl-vinyl)-4-(tetrahydro-pyran-2-yloxy)-butyl 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: 80.0%

: 5927-18-4
trimethyl phosphonoacetate

: 128694-42-8
Benzoic acid (R)-1-formyl-4-(tetrahydro-pyran-2-yloxy)-butyl ester

: 128778-20-1
Benzoic acid (R)-1-((E)-2-methoxycarbonyl-vinyl)-4-(tetrahydro-pyran-2-yloxy)-butyl ester

Guidance literature:: With sodium hydride; In benzene; at 0 ℃; for 0.0833333h;
DOI:10.1021/jo9619241

Reference yield:

: 51326-51-3
4-(tetrahydropyran-2-yloxy)butan-1-ol

: 128778-20-1
Benzoic acid (R)-1-((E)-2-methoxycarbonyl-vinyl)-4-(tetrahydro-pyran-2-yloxy)-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: SO₃-Py, Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.5 h / Ambient temperature

2: 83 percent / piperidine / pyridine / 2 h / 60 °C

3: 88 percent / DIBAL / diethyl ether; hexane / 0.5 h / 0 °C

4: 81 percent / Ti(OPr-i)4, (R,R)-(+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

5: 80 percent / Ti(OPr-i)4 / CH₂Cl₂ / 4 h / Ambient temperature

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

7: 80 percent / NaH / benzene / 0.08 h / 0 °C

With piperidine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; pyridine; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; benzene;
DOI:10.1021/jo9619241

Reference yield:

: 66084-36-4
(E)-(R)-(tetrahydro-pyran-2-yloxy)-hex-2-en-1-ol

: 128778-20-1
Benzoic acid (R)-1-((E)-2-methoxycarbonyl-vinyl)-4-(tetrahydro-pyran-2-yloxy)-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 81 percent / Ti(OPr-i)4, (R,R)-(+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

2: 80 percent / Ti(OPr-i)4 / CH₂Cl₂ / 4 h / Ambient temperature

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

4: 80 percent / NaH / benzene / 0.08 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; diethyl (2R,3R)-tartrate; sodium hydride; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; water; benzene;
DOI:10.1021/jo9619241