Benzoic acid (E)-(R)-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-3-methoxycarbonyl-allyl ester

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Chemical Name:Benzoic acid (E)-(R)-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-3-methoxycarbonyl-allyl ester
CAS No.:192122-54-6
Molecular Formula:C₁₈H₂₂O₆
Molecular Weight:334.369
Hs Code.:

Synonyms:Benzoic acid (E)-(R)-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-3-methoxycarbonyl-allyl ester

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Chemical Property of Benzoic acid (E)-(R)-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-3-methoxycarbonyl-allyl ester

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Technology Process of Benzoic acid (E)-(R)-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-3-methoxycarbonyl-allyl ester

There total 18 articles about Benzoic acid (E)-(R)-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-3-methoxycarbonyl-allyl 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: 92.0%

: 192122-53-5
Benzoic acid (E)-(R)-1-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-3-methoxycarbonyl-allyl ester

: 192122-54-6
Benzoic acid (E)-(R)-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-3-methoxycarbonyl-allyl ester

Guidance literature:: With hydrogen fluoride; In acetonitrile; for 12h; Ambient temperature;
DOI:10.1021/jo9619241

Reference yield:

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

: 192122-54-6
Benzoic acid (E)-(R)-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-3-methoxycarbonyl-allyl ester

Guidance literature:: Multi-step reaction with 18 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

5: 95 percent / conc. HCl / methanol / 0.08 h / pH 1

6: 9 percent / NaH / tetrahydrofuran / 4 h / -78 °C

7: 95 percent / NaH / tetrahydrofuran / 4 h / -78 °C

8: 73 percent / DIBAL / diethyl ether; hexane / 0.5 h / 0 °C

9: 93 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

10: 85 percent / imidazole / CH₂Cl₂ / 12 h / Ambient temperature

11: 96 percent / NaH, / CH₂Cl₂; methanol / 0.08 h

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

13: 89 percent / piperidine / pyridine / 2 h / 60 °C

14: 78 percent / DIBAL / diethyl ether; hexane / 0.5 h

15: 80 percent / Ti(OPr-i)4, (R,R)-(+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

16: 87 percent / Ti(OPr-i)4 / dimethylsulfoxide / 4 h / Ambient temperature

17: 1.) NaIO₄, 2.) NaH / 1.) THF, H₂O, room temperature, 2 h, 2.) THF, -78 deg C, 30 min

18: 92 percent / aq. HF / acetonitrile / 12 h / Ambient temperature

With piperidine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; hydrogen fluoride; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; pyridine; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; acetonitrile; benzene;
DOI:10.1021/jo9619241

Reference yield:

: 127280-22-2
{(2S,3S)-3-[3-(Tetrahydro-pyran-2-yloxy)-propyl]-oxiranyl}-methanol

: 192122-54-6
Benzoic acid (E)-(R)-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-3-methoxycarbonyl-allyl ester

Guidance literature:: Multi-step reaction with 17 steps

1: 80 percent / Ti(OPr-i)4 / CH₂Cl₂ / 4 h / Ambient temperature

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

3: 80 percent / NaH / benzene / 0.08 h / 0 °C

4: 95 percent / conc. HCl / methanol / 0.08 h / pH 1

5: 9 percent / NaH / tetrahydrofuran / 4 h / -78 °C

6: 95 percent / NaH / tetrahydrofuran / 4 h / -78 °C

7: 73 percent / DIBAL / diethyl ether; hexane / 0.5 h / 0 °C

8: 93 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

9: 85 percent / imidazole / CH₂Cl₂ / 12 h / Ambient temperature

10: 96 percent / NaH, / CH₂Cl₂; methanol / 0.08 h

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

12: 89 percent / piperidine / pyridine / 2 h / 60 °C

13: 78 percent / DIBAL / diethyl ether; hexane / 0.5 h

14: 80 percent / Ti(OPr-i)4, (R,R)-(+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

15: 87 percent / Ti(OPr-i)4 / dimethylsulfoxide / 4 h / Ambient temperature

16: 1.) NaIO₄, 2.) NaH / 1.) THF, H₂O, room temperature, 2 h, 2.) THF, -78 deg C, 30 min

17: 92 percent / aq. HF / acetonitrile / 12 h / Ambient temperature

With piperidine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; hydrogen fluoride; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; pyridine; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; acetonitrile; benzene;
DOI:10.1021/jo9619241