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

Base Information

Chemical Name: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
CAS No.:303158-50-1
Molecular Formula:C₃₈H₅₁NO₈Si
Molecular Weight:677.91
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 12 articles about 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 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: 95.0%

: 303158-75-0
2,2-Dimethyl-propionic acid 2-{(2S,4R,6R)-6-[(E)-(R)-1-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-3-methyl-but-2-enyl]-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl}-oxazol-4-ylmethyl ester

: 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

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane;
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

: 303158-50-1
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

Guidance literature:: Multi-step reaction with 11 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

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; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; silver(l) oxide; In tetrahydrofuran; 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;
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

: 303158-50-1
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

Guidance literature:: Multi-step reaction with 12 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

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; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; silver(l) oxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; 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;
DOI:10.1021/ol0063656