2,2-Dimethyl-propionic acid (3R,7S)-3-(tert-butyl-dimethyl-silanyloxy)-8-{(2S,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-5-methylene-7-(toluene-4-sulfonyloxy)-octyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (3R,7S)-3-(tert-butyl-dimethyl-silanyloxy)-8-{(2S,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-5-methylene-7-(toluene-4-sulfonyloxy)-octyl ester
CAS No.:224578-36-3
Molecular Formula:C₆₀H₈₃NO₁₁SSi₂
Molecular Weight:1082.56
Hs Code.:

2,2-Dimethyl-propionic acid (3R,7S)-3-(tert-butyl-dimethyl-silanyloxy)-8-{(2S,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-5-methylene-7-(toluene-4-sulfonyloxy)-octyl ester

Synonyms:2,2-Dimethyl-propionic acid (3R,7S)-3-(tert-butyl-dimethyl-silanyloxy)-8-{(2S,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-5-methylene-7-(toluene-4-sulfonyloxy)-octyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (3R,7S)-3-(tert-butyl-dimethyl-silanyloxy)-8-{(2S,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-5-methylene-7-(toluene-4-sulfonyloxy)-octyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (3R,7S)-3-(tert-butyl-dimethyl-silanyloxy)-8-{(2S,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-5-methylene-7-(toluene-4-sulfonyloxy)-octyl ester

There total 19 articles about 2,2-Dimethyl-propionic acid (3R,7S)-3-(tert-butyl-dimethyl-silanyloxy)-8-{(2S,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-5-methylene-7-(toluene-4-sulfonyloxy)-octyl 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: 82.0%

: 98-59-9
p-toluenesulfonyl chloride

: 224578-22-7
2,2-Dimethyl-propionic acid (3R,7S)-3-(tert-butyl-dimethyl-silanyloxy)-8-{(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-7-hydroxy-5-methylene-octyl ester

: 224578-36-3
2,2-Dimethyl-propionic acid (3R,7S)-3-(tert-butyl-dimethyl-silanyloxy)-8-{(2S,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-5-methylene-7-(toluene-4-sulfonyloxy)-octyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane;
DOI:10.1016/S0040-4039(99)00209-9

Reference yield:

: 88920-24-5
p-methoxybenzyloxy acetic acid

: 224578-36-3
2,2-Dimethyl-propionic acid (3R,7S)-3-(tert-butyl-dimethyl-silanyloxy)-8-{(2S,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-5-methylene-7-(toluene-4-sulfonyloxy)-octyl ester

Guidance literature:: Multi-step reaction with 18 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

14: 91 percent / imidazol / dimethylformamide

15: 95 percent / LiOH / tetrahydrofuran; methanol; H₂O

16: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

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

18: 82 percent / DMAP, Et₃N / CH₂Cl₂

With 1H-imidazole; dmap; lithium hydroxide; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; Bromotrichloromethane; (S,S)-1,2-diamino-1,2-diphenylethane bis-sulfonamide; (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; dimethyl sulfoxide; 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; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4039(99)00209-9

Reference yield:

: 224578-16-9
2-(4-Methoxy-benzyloxymethyl)-oxazole-4-carbaldehyde

: 224578-36-3
2,2-Dimethyl-propionic acid (3R,7S)-3-(tert-butyl-dimethyl-silanyloxy)-8-{(2S,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-5-methylene-7-(toluene-4-sulfonyloxy)-octyl ester

Guidance literature:: Multi-step reaction with 14 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

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; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; boron tribromide; L-Selectride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4039(99)00209-9