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

Base Information

• Chemical Name: Benzoic acid (E)-(R)-1-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-3-methoxycarbonyl-allyl ester
• CAS No.: 192122-53-5
• Molecular Formula: C₃₄H₄₀O₆Si
• Molecular Weight: 572.774

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

Chemical Property of Benzoic acid (E)-(R)-1-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-3-methoxycarbonyl-allyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (E)-(R)-1-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-3-methoxycarbonyl-allyl ester

There total 17 articles about Benzoic acid (E)-(R)-1-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-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:

(E)-(R)-(tetrahydro-pyran-2-yloxy)-hex-2-en-1-ol (66084-36-4) → Benzoic acid (E)-(R)-1-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-3-methoxycarbonyl-allyl ester (192122-53-5)

Guidance literature:

Multi-step reaction with 17 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

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

DOI:10.1021/jo9619241

Reference yield:

(E)-methyl-6-[(tetrahydro-2H-pyran-2-yl)oxy]-hex-2-en-oate (127089-43-4) → Benzoic acid (E)-(R)-1-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-3-methoxycarbonyl-allyl ester (192122-53-5)

Guidance literature:

Multi-step reaction with 18 steps

1: 88 percent / DIBAL / diethyl ether; hexane / 0.5 h / 0 °C

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

3: 80 percent / Ti(OPr-i)4 / CH₂Cl₂ / 4 h / Ambient temperature

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

5: 80 percent / NaH / benzene / 0.08 h / 0 °C

6: 95 percent / conc. HCl / methanol / 0.08 h / pH 1

7: 9 percent / NaH / tetrahydrofuran / 4 h / -78 °C

8: 95 percent / NaH / tetrahydrofuran / 4 h / -78 °C

9: 73 percent / DIBAL / diethyl ether; hexane / 0.5 h / 0 °C

10: 93 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

11: 85 percent / imidazole / CH₂Cl₂ / 12 h / Ambient temperature

12: 96 percent / NaH, / CH₂Cl₂; methanol / 0.08 h

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

14: 89 percent / piperidine / pyridine / 2 h / 60 °C

15: 78 percent / DIBAL / diethyl ether; hexane / 0.5 h

16: 80 percent / Ti(OPr-i)4, (R,R)-(+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

17: 87 percent / Ti(OPr-i)4 / dimethylsulfoxide / 4 h / Ambient temperature

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

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

DOI:10.1021/jo9619241

Reference yield:

Benzoic acid (R)-1-formyl-4-(tetrahydro-pyran-2-yloxy)-butyl ester (128694-42-8) → Benzoic acid (E)-(R)-1-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-3-methoxycarbonyl-allyl ester (192122-53-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 80 percent / NaH / benzene / 0.08 h / 0 °C

2: 95 percent / conc. HCl / methanol / 0.08 h / pH 1

3: 9 percent / NaH / tetrahydrofuran / 4 h / -78 °C

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

5: 73 percent / DIBAL / diethyl ether; hexane / 0.5 h / 0 °C

6: 93 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

7: 85 percent / imidazole / CH₂Cl₂ / 12 h / Ambient temperature

8: 96 percent / NaH, / CH₂Cl₂; methanol / 0.08 h

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

10: 89 percent / piperidine / pyridine / 2 h / 60 °C

11: 78 percent / DIBAL / diethyl ether; hexane / 0.5 h

12: 80 percent / Ti(OPr-i)4, (R,R)-(+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

13: 87 percent / Ti(OPr-i)4 / dimethylsulfoxide / 4 h / Ambient temperature

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

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

DOI:10.1021/jo9619241

upstream raw materials:

(E)-(R)-(tetrahydro-pyran-2-yloxy)-hex-2-en-1-ol

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

(E)-methyl-6-[(tetrahydro-2H-pyran-2-yl)oxy]-hex-2-en-oate

Benzoic acid (R)-1-formyl-4-(tetrahydro-pyran-2-yloxy)-butyl ester

Downstream raw materials:

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

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