2,2-Dimethyl-propionic acid 2-{(2R,4R,6R)-4-hydroxy-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-ethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid 2-{(2R,4R,6R)-4-hydroxy-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-ethyl ester
• CAS No.: 224578-34-1
• Molecular Formula: C₂₄H₃₃NO₇
• Molecular Weight: 447.529

Synonyms:2,2-Dimethyl-propionic acid 2-{(2R,4R,6R)-4-hydroxy-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-ethyl ester

Chemical Property of 2,2-Dimethyl-propionic acid 2-{(2R,4R,6R)-4-hydroxy-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-ethyl ester

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of 2,2-Dimethyl-propionic acid 2-{(2R,4R,6R)-4-hydroxy-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-ethyl ester

There total 14 articles about 2,2-Dimethyl-propionic acid 2-{(2R,4R,6R)-4-hydroxy-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-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%

2,2-Dimethyl-propionic acid 2-{(2R,6R)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-4-oxo-tetrahydro-pyran-2-yl}-ethyl ester (224578-33-0) → 2,2-Dimethyl-propionic acid 2-{(2R,4R,6R)-4-hydroxy-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-ethyl ester (224578-34-1)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(99)00209-9

Reference yield:

p-methoxybenzyloxy acetic acid (88920-24-5) → 2,2-Dimethyl-propionic acid 2-{(2R,4R,6R)-4-hydroxy-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-ethyl ester (224578-34-1)

Guidance literature:

Multi-step reaction with 13 steps

2: DAST

3: 81 percent / BrCCl₃, DBU

4: 90 percent / DIBAL / CH₂Cl₂ / 0.17 h / -78 °C

5: 1.) (R,R)-1,2-diamino-1,2-diphenylethane bis-sulfonamide, BBr₃ / 1.) CH₂Cl₂, 12 h, 2.) CH₂Cl₂, -78 deg C

6: PPTs / CH₂Cl₂

7: TBAF / tetrahydrofuran

8: Et₃N / CH₂Cl₂

9: TsOH / methanol

10: NaH / toluene

11: 99 percent / OsO₄, K₃Fe(CN)6, K₂CO₃, NaHCO₃ / 2-methyl-propan-2-ol; H₂O

12: 98 percent / NaIO₄ / tetrahydrofuran; H₂O

13: 85 percent / L-Selectride / tetrahydrofuran / -78 °C

With sodium periodate; osmium(VIII) oxide; Bromotrichloromethane; (R,R)-1,2-diamino-1,2-diphenylethane bis-sulfonamide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; boron tribromide; L-Selectride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(99)00209-9

Reference yield:

2-(4-Methoxy-benzyloxymethyl)-oxazole-4-carbaldehyde (224578-16-9) → 2,2-Dimethyl-propionic acid 2-{(2R,4R,6R)-4-hydroxy-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-ethyl ester (224578-34-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) (R,R)-1,2-diamino-1,2-diphenylethane bis-sulfonamide, BBr₃ / 1.) CH₂Cl₂, 12 h, 2.) CH₂Cl₂, -78 deg C

2: PPTs / CH₂Cl₂

3: TBAF / tetrahydrofuran

4: Et₃N / CH₂Cl₂

5: TsOH / methanol

6: NaH / toluene

7: 99 percent / OsO₄, K₃Fe(CN)6, K₂CO₃, NaHCO₃ / 2-methyl-propan-2-ol; H₂O

8: 98 percent / NaIO₄ / tetrahydrofuran; H₂O

9: 85 percent / L-Selectride / tetrahydrofuran / -78 °C

With sodium periodate; osmium(VIII) oxide; (R,R)-1,2-diamino-1,2-diphenylethane bis-sulfonamide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; boron tribromide; L-Selectride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(99)00209-9

upstream raw materials:

2,2-Dimethyl-propionic acid 2-{(2R,6R)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-4-oxo-tetrahydro-pyran-2-yl}-ethyl ester

p-methoxybenzyloxy acetic acid

2-(4-Methoxy-benzyloxymethyl)-oxazole-4-carbaldehyde

2,2-Dimethyl-propionic acid (3R,7R)-3-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-7-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-5-methylene-heptyl ester

Downstream raw materials:

2,2-Dimethyl-propionic acid 2-{(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-ethyl ester

{(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-acetaldehyde

2-{(2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-ethanol

2,2-Dimethyl-propionic acid 2-{(2R,6R)-6-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-(2-hydroxymethyl-oxazol-4-yl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-ethyl ester

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