2,2-Dimethyl-propionic acid (E)-(R)-4-(tert-butyl-diphenyl-silanyloxy)-4-[(2R,4R,6S)-6-(4-hydroxymethyl-oxazol-2-ylmethyl)-4,6-dimethoxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-enyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (E)-(R)-4-(tert-butyl-diphenyl-silanyloxy)-4-[(2R,4R,6S)-6-(4-hydroxymethyl-oxazol-2-ylmethyl)-4,6-dimethoxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-enyl ester
CAS No.:553636-28-5
Molecular Formula:C₃₈H₅₃NO₈Si
Molecular Weight:679.926
Hs Code.:

2,2-Dimethyl-propionic acid (E)-(R)-4-(tert-butyl-diphenyl-silanyloxy)-4-[(2R,4R,6S)-6-(4-hydroxymethyl-oxazol-2-ylmethyl)-4,6-dimethoxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-enyl ester

Synonyms:2,2-Dimethyl-propionic acid (E)-(R)-4-(tert-butyl-diphenyl-silanyloxy)-4-[(2R,4R,6S)-6-(4-hydroxymethyl-oxazol-2-ylmethyl)-4,6-dimethoxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-enyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (E)-(R)-4-(tert-butyl-diphenyl-silanyloxy)-4-[(2R,4R,6S)-6-(4-hydroxymethyl-oxazol-2-ylmethyl)-4,6-dimethoxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-enyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (E)-(R)-4-(tert-butyl-diphenyl-silanyloxy)-4-[(2R,4R,6S)-6-(4-hydroxymethyl-oxazol-2-ylmethyl)-4,6-dimethoxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-enyl ester

There total 11 articles about 2,2-Dimethyl-propionic acid (E)-(R)-4-(tert-butyl-diphenyl-silanyloxy)-4-[(2R,4R,6S)-6-(4-hydroxymethyl-oxazol-2-ylmethyl)-4,6-dimethoxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-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: 92.0%

: 553636-19-4
2,2-Dimethyl-propionic acid (E)-(R)-4-(tert-butyl-diphenyl-silanyloxy)-4-{(2R,4R,6S)-6-[4-(tert-butyl-diphenyl-silanyloxymethyl)-oxazol-2-ylmethyl]-4,6-dimethoxy-tetrahydro-pyran-2-yl}-2-methyl-but-2-enyl ester

: 553636-28-5
2,2-Dimethyl-propionic acid (E)-(R)-4-(tert-butyl-diphenyl-silanyloxy)-4-[(2R,4R,6S)-6-(4-hydroxymethyl-oxazol-2-ylmethyl)-4,6-dimethoxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-enyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1002/anie.200390322

Reference yield:

: 2,2-dimethyl-propionic acid 7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-methyl-octa-2,7-dienyl ester

: 553636-28-5
2,2-Dimethyl-propionic acid (E)-(R)-4-(tert-butyl-diphenyl-silanyloxy)-4-[(2R,4R,6S)-6-(4-hydroxymethyl-oxazol-2-ylmethyl)-4,6-dimethoxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-enyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: OsO₄; K₃Fe(CN)6; 1,4-diazabicyclo[2.2.2]octane / K₂CO₃; NaHCO₃ / H₂O; 2-methyl-propan-2-ol

2.1: NaIO₄ / tetrahydrofuran; H₂O

3.1: 94 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / 10 h / -20 °C

4.1: camphorsulfonic acid / 16 h / 20 °C

5.1: HF*pyridine / tetrahydrofuran

6.1: (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 °C

7.1: SmI₂ / tetrahydrofuran / 20 °C

8.1: DMSO; (CF₃CO)2O / CH₂Cl₂ / -78 °C

8.2: 88 percent / acetylacetone; triethylamine / CH₂Cl₂ / -60 - -40 °C

9.1: camphorsulfonic acid / 1.5 h / 20 °C

10.1: 90 percent / CaSO₄; Ag₂O / 72 h

11.1: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

With 1,4-diaza-bicyclo[2.2.2]octane; calcium sulfate; sodium periodate; osmium(VIII) oxide; samarium diiodide; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; silver(l) oxide; tetramethylammonium triacetoxyborohydride; potassium hexacyanoferrate(III); sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; dichloromethane; water; acetic acid; acetonitrile; tert-butyl alcohol; 7.1: Barbier coupling;
DOI:10.1002/anie.200390322

Reference yield:

: 2,2-Dimethyl-propionic acid (E)-(R)-4-(tert-butyl-diphenyl-silanyloxy)-4-[6-(2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-methyl-but-2-enyl ester

: 553636-28-5
2,2-Dimethyl-propionic acid (E)-(R)-4-(tert-butyl-diphenyl-silanyloxy)-4-[(2R,4R,6S)-6-(4-hydroxymethyl-oxazol-2-ylmethyl)-4,6-dimethoxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 °C

2.1: SmI₂ / tetrahydrofuran / 20 °C

3.1: DMSO; (CF₃CO)2O / CH₂Cl₂ / -78 °C

3.2: 88 percent / acetylacetone; triethylamine / CH₂Cl₂ / -60 - -40 °C

4.1: camphorsulfonic acid / 1.5 h / 20 °C

5.1: 90 percent / CaSO₄; Ag₂O / 72 h

6.1: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

With calcium sulfate; samarium diiodide; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; silver(l) oxide; In tetrahydrofuran; dichloromethane; 2.1: Barbier coupling;
DOI:10.1002/anie.200390322