2,2-dimethylpropionic acid 2-{(2S,4R,6R)-6-[(R)-(E)-1-(tert-butyldiphenylsilanyl-oxy)-4-(tert-butylmethoxyphenylsilanyloxy)-3-methyl-but-2-enyl]-4-hydroxy-2-methoxy-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)-4-(tert-butylmethoxyphenylsilanyloxy)-3-methyl-but-2-enyl]-4-hydroxy-2-methoxy-tetrahydropyran-2-ylmethyl}-oxazol-4-ylmethyl ester
CAS No.:303158-60-3
Molecular Formula:C₄₈H₆₇NO₉Si₂
Molecular Weight:858.232
Hs Code.:

2,2-dimethylpropionic acid 2-{(2S,4R,6R)-6-[(R)-(E)-1-(tert-butyldiphenylsilanyl-oxy)-4-(tert-butylmethoxyphenylsilanyloxy)-3-methyl-but-2-enyl]-4-hydroxy-2-methoxy-tetrahydropyran-2-ylmethyl}-oxazol-4-ylmethyl ester

Synonyms:2,2-dimethylpropionic acid 2-{(2S,4R,6R)-6-[(R)-(E)-1-(tert-butyldiphenylsilanyl-oxy)-4-(tert-butylmethoxyphenylsilanyloxy)-3-methyl-but-2-enyl]-4-hydroxy-2-methoxy-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)-4-(tert-butylmethoxyphenylsilanyloxy)-3-methyl-but-2-enyl]-4-hydroxy-2-methoxy-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)-4-(tert-butylmethoxyphenylsilanyloxy)-3-methyl-but-2-enyl]-4-hydroxy-2-methoxy-tetrahydropyran-2-ylmethyl}-oxazol-4-ylmethyl ester

There total 10 articles about 2,2-dimethylpropionic acid 2-{(2S,4R,6R)-6-[(R)-(E)-1-(tert-butyldiphenylsilanyl-oxy)-4-(tert-butylmethoxyphenylsilanyloxy)-3-methyl-but-2-enyl]-4-hydroxy-2-methoxy-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: 91.0%

: 94124-39-7
tert-butylphenylmethoxysilyl bromide

: 303158-61-4
2,2-Dimethyl-propionic acid 2-{(2S,4R,6R)-6-[(E)-(R)-1-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-3-methyl-but-2-enyl]-4-hydroxy-2-methoxy-tetrahydro-pyran-2-ylmethyl}-oxazol-4-ylmethyl ester

: 303158-60-3
2,2-dimethylpropionic acid 2-{(2S,4R,6R)-6-[(R)-(E)-1-(tert-butyldiphenylsilanyl-oxy)-4-(tert-butylmethoxyphenylsilanyloxy)-3-methyl-but-2-enyl]-4-hydroxy-2-methoxy-tetrahydropyran-2-ylmethyl}-oxazol-4-ylmethyl ester

Guidance literature:: With triethylamine; In dichloromethane;
DOI:10.1021/ol0063656

Reference yield: 42.0%

: 67-56-1
methanol

: 303158-72-7
2,2-dimethyl-propionic acid 2-[4,6-bis-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-10-(tert-butyl-methoxy-phenyl-silanyloxy)-2-hydroxy-9-methyl-dec-8-enyl]-oxazol-4-ylmethyl ester

: 303158-61-4
2,2-Dimethyl-propionic acid 2-{(2S,4R,6R)-6-[(E)-(R)-1-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-3-methyl-but-2-enyl]-4-hydroxy-2-methoxy-tetrahydro-pyran-2-ylmethyl}-oxazol-4-ylmethyl ester

: 303158-60-3
2,2-dimethylpropionic acid 2-{(2S,4R,6R)-6-[(R)-(E)-1-(tert-butyldiphenylsilanyl-oxy)-4-(tert-butylmethoxyphenylsilanyloxy)-3-methyl-but-2-enyl]-4-hydroxy-2-methoxy-tetrahydropyran-2-ylmethyl}-oxazol-4-ylmethyl ester

Guidance literature:: With pyridinium p-toluenesulfonate; at 50 ℃; for 40h;
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

: 303158-60-3
2,2-dimethylpropionic acid 2-{(2S,4R,6R)-6-[(R)-(E)-1-(tert-butyldiphenylsilanyl-oxy)-4-(tert-butylmethoxyphenylsilanyloxy)-3-methyl-but-2-enyl]-4-hydroxy-2-methoxy-tetrahydropyran-2-ylmethyl}-oxazol-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 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

With 2,3,5-trimethyl-pyridine; samarium diiodide; oxalyl dichloride; 2,3-dimercapto-succinic acid; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: silylation / 2: ether cleavage / 3: silylation / 4: Reduction / 5: Oxidation / 6: Condensation / 7: Cyclization / 8: silylation;
DOI:10.1021/ol0063656