Benzoic acid 2-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-ethyl ester

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Chemical Name:Benzoic acid 2-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-ethyl ester
CAS No.:192122-42-2
Molecular Formula:C₃₀H₃₆O₄Si
Molecular Weight:488.699
Hs Code.:

Synonyms:Benzoic acid 2-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-ethyl ester

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Chemical Property of Benzoic acid 2-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-ethyl ester

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Technology Process of Benzoic acid 2-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-ethyl ester

There total 12 articles about Benzoic acid 2-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-ethyl 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: 85.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 192122-39-7
Benzoic acid 2-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-yl)-ethyl ester

: 192122-42-2
Benzoic acid 2-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-ethyl ester

Guidance literature:: With 1H-imidazole; In dichloromethane; for 12h; Ambient temperature;
DOI:10.1021/jo9619241

Reference yield:

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

: 192122-42-2
Benzoic acid 2-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 10 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

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

Reference yield:

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

: 192122-42-2
Benzoic acid 2-[(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 9 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

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; sodium periodate; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; benzene;
DOI:10.1021/jo9619241