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

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid 2-{(2R,6R)-6-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-(2-iodomethyl-oxazol-4-yl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-ethyl ester
• CAS No.: 224578-38-5
• Molecular Formula: C₃₉H₅₂INO₆Si
• Molecular Weight: 785.835

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

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

Chemical Property:

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

There total 22 articles about 2,2-Dimethyl-propionic acid 2-{(2R,6R)-6-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-(2-iodomethyl-oxazol-4-yl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-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: 97.0%

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 (224578-37-4) → 2,2-Dimethyl-propionic acid 2-{(2R,6R)-6-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-(2-iodomethyl-oxazol-4-yl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-ethyl ester (224578-38-5)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane;

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,6R)-6-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-(2-iodomethyl-oxazol-4-yl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-ethyl ester (224578-38-5)

Guidance literature:

Multi-step reaction with 18 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

10: 91 percent / imidazol / dimethylformamide

11: 95 percent / LiOH / tetrahydrofuran; methanol; H₂O

12: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

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

14: 82 percent / DMAP, Et₃N / CH₂Cl₂

15: 90 percent / HF*pyr / acetonitrile

16: 89 percent / NaH / benzene / Heating

17: 91 percent / DDQ, pH 7 buffer / 2-methyl-propan-2-ol; CH₂Cl₂

18: 97 percent / PPh₃, I₂, imidazole / CH₂Cl₂

With 1H-imidazole; dmap; lithium hydroxide; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; (S,S)-1,2-diamino-1,2-diphenylethane bis-sulfonamide; (R,R)-1,2-diamino-1,2-diphenylethane bis-sulfonamide; pH 7 buffer; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; boron tribromide; L-Selectride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene;

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

Reference yield:

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 (224578-18-1) → 2,2-Dimethyl-propionic acid 2-{(2R,6R)-6-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-(2-iodomethyl-oxazol-4-yl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-ethyl ester (224578-38-5)

Guidance literature:

Multi-step reaction with 17 steps

1: PPTs / CH₂Cl₂

2: TBAF / tetrahydrofuran

3: Et₃N / CH₂Cl₂

4: TsOH / methanol

5: NaH / toluene

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

7: 98 percent / NaIO₄ / tetrahydrofuran; H₂O

8: 85 percent / L-Selectride / tetrahydrofuran / -78 °C

9: 91 percent / imidazol / dimethylformamide

10: 95 percent / LiOH / tetrahydrofuran; methanol; H₂O

11: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

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

13: 82 percent / DMAP, Et₃N / CH₂Cl₂

14: 90 percent / HF*pyr / acetonitrile

15: 89 percent / NaH / benzene / Heating

16: 91 percent / DDQ, pH 7 buffer / 2-methyl-propan-2-ol; CH₂Cl₂

17: 97 percent / PPh₃, I₂, imidazole / CH₂Cl₂

With 1H-imidazole; dmap; lithium hydroxide; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; (S,S)-1,2-diamino-1,2-diphenylethane bis-sulfonamide; pH 7 buffer; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; boron tribromide; L-Selectride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene;

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

upstream raw materials:

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

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

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

Downstream raw materials:

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

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