2,2-Dimethyl-propionic acid 2-{(2S,4R,6R)-6-[(2E,4Z,8E)-(1R,6R)-9-bromo-1-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-3-methyl-nona-2,4,8-trienyl]-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl}-oxazol-4-ylmethyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid 2-{(2S,4R,6R)-6-[(2E,4Z,8E)-(1R,6R)-9-bromo-1-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-3-methyl-nona-2,4,8-trienyl]-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl}-oxazol-4-ylmethyl ester
CAS No.:303158-62-5
Molecular Formula:C₄₄H₆₀BrNO₈Si
Molecular Weight:838.952
Hs Code.:

2,2-Dimethyl-propionic acid 2-{(2S,4R,6R)-6-[(2E,4Z,8E)-(1R,6R)-9-bromo-1-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-3-methyl-nona-2,4,8-trienyl]-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl}-oxazol-4-ylmethyl ester

Synonyms:2,2-Dimethyl-propionic acid 2-{(2S,4R,6R)-6-[(2E,4Z,8E)-(1R,6R)-9-bromo-1-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-3-methyl-nona-2,4,8-trienyl]-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl}-oxazol-4-ylmethyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid 2-{(2S,4R,6R)-6-[(2E,4Z,8E)-(1R,6R)-9-bromo-1-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-3-methyl-nona-2,4,8-trienyl]-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl}-oxazol-4-ylmethyl ester

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Technology Process of 2,2-Dimethyl-propionic acid 2-{(2S,4R,6R)-6-[(2E,4Z,8E)-(1R,6R)-9-bromo-1-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-3-methyl-nona-2,4,8-trienyl]-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl}-oxazol-4-ylmethyl ester

There total 19 articles about 2,2-Dimethyl-propionic acid 2-{(2S,4R,6R)-6-[(2E,4Z,8E)-(1R,6R)-9-bromo-1-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-3-methyl-nona-2,4,8-trienyl]-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl}-oxazol-4-ylmethyl 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: 60.0%

: 303158-49-8
(E)-((R)-5-bromo-2-methoxy-pent-4-ene-1-sulfonyl)-1-phenyl-1H-tetrazole

: 303158-50-1
2,2-dimethylpropionic acid 2-{(2S,4R,6R)-6-[(R)-(E)-1-(tert-butyldiphenylsilanyl-oxy)-3-but-2-en-4-al]-2,4-dimethoxy-tetrahydropyran-2-ylmethyl}-oxazol-4-ylmethyl ester

: 2,2-Dimethyl-propionic acid 2-{(2S,4R,6R)-6-[(2E,4E,6E,8E)-(R)-9-bromo-1-(tert-butyl-diphenyl-silanyloxy)-3-methyl-nona-2,4,6,8-tetraenyl]-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl}-oxazol-4-ylmethyl ester

: 303158-62-5
2,2-Dimethyl-propionic acid 2-{(2S,4R,6R)-6-[(2E,4Z,8E)-(1R,6R)-9-bromo-1-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-3-methyl-nona-2,4,8-trienyl]-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl}-oxazol-4-ylmethyl ester

Guidance literature:: With potassium hexamethylsilazane; In 1,2-dimethoxyethane; at -78 ℃;
DOI:10.1021/ol0063656

Reference yield:

: 2,2-Dimethyl-propionic acid (E)-(3S,5R,6R)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dihydroxy-9-methoxymethoxy-8-methyl-non-7-enyl ester

: 303158-62-5
2,2-Dimethyl-propionic acid 2-{(2S,4R,6R)-6-[(2E,4Z,8E)-(1R,6R)-9-bromo-1-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-3-methyl-nona-2,4,8-trienyl]-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl}-oxazol-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 95 percent / collidine / CH₂Cl₂ / 0 °C

2: 83 percent / BF₃*OEt₂; DMS

3: 98 percent / Et₃N / CH₂Cl₂

4: 88 percent / DIBAL / CH₂Cl₂ / 0 °C

5: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

6: 76 percent / SmI₂ / tetrahydrofuran / 0.25 h / 20 °C

7: 21 percent / pyridinium para-toluenesulfonate / 40 h / 50 °C

8: 91 percent / Et₃N / CH₂Cl₂

9: 85 percent / Ag₂O; CaSO₄

10: 95 percent / TBAF / 1,2-dichloro-ethane

11: 95 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

12: 60 percent / KHMDS / 1,2-dimethoxy-ethane / -78 °C

With pyridine; 2,3,5-trimethyl-pyridine; calcium sulfate; samarium diiodide; oxalyl dichloride; 2,3-dimercapto-succinic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; silver(l) oxide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 1,2-dichloro-ethane; 1: silylation / 2: ether cleavage / 3: silylation / 4: Reduction / 5: Oxidation / 6: Condensation / 7: Cyclization / 8: silylation / 9: Methylation / 10: desilylation / 11: Oxidation / 12: Condensation;
DOI:10.1021/ol0063656

Reference yield:

: 303158-67-0
2,2-Dimethyl-propionic acid (E)-(5R,6R)-6-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-9-methoxymethoxy-8-methyl-3-oxo-non-7-enyl ester

: 303158-62-5
2,2-Dimethyl-propionic acid 2-{(2S,4R,6R)-6-[(2E,4Z,8E)-(1R,6R)-9-bromo-1-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-3-methyl-nona-2,4,8-trienyl]-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl}-oxazol-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 97 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile

2: 95 percent / collidine / CH₂Cl₂ / 0 °C

3: 83 percent / BF₃*OEt₂; DMS

4: 98 percent / Et₃N / CH₂Cl₂

5: 88 percent / DIBAL / CH₂Cl₂ / 0 °C

6: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

7: 76 percent / SmI₂ / tetrahydrofuran / 0.25 h / 20 °C

8: 21 percent / pyridinium para-toluenesulfonate / 40 h / 50 °C

9: 91 percent / Et₃N / CH₂Cl₂

10: 85 percent / Ag₂O; CaSO₄

11: 95 percent / TBAF / 1,2-dichloro-ethane

12: 95 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

13: 60 percent / KHMDS / 1,2-dimethoxy-ethane / -78 °C

With pyridine; 2,3,5-trimethyl-pyridine; calcium sulfate; samarium diiodide; oxalyl dichloride; 2,3-dimercapto-succinic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; silver(l) oxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; acetic acid; 1,2-dichloro-ethane; acetonitrile; 1: Reduction / 2: silylation / 3: ether cleavage / 4: silylation / 5: Reduction / 6: Oxidation / 7: Condensation / 8: Cyclization / 9: silylation / 10: Methylation / 11: desilylation / 12: Oxidation / 13: Condensation;
DOI:10.1021/ol0063656