Acetic acid (E)-(4S,5R,6S,7R)-4-benzyloxy-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-7-((2S,3R)-3-vinyl-oxiranyl)-hept-2-enyl ester

Base Information

Chemical Name:Acetic acid (E)-(4S,5R,6S,7R)-4-benzyloxy-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-7-((2S,3R)-3-vinyl-oxiranyl)-hept-2-enyl ester
CAS No.:182411-51-4
Molecular Formula:C₄₀H₆₂O₈Si₂
Molecular Weight:727.098
Hs Code.:

Synonyms:Acetic acid (E)-(4S,5R,6S,7R)-4-benzyloxy-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-7-((2S,3R)-3-vinyl-oxiranyl)-hept-2-enyl ester

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Chemical Property of Acetic acid (E)-(4S,5R,6S,7R)-4-benzyloxy-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-7-((2S,3R)-3-vinyl-oxiranyl)-hept-2-enyl ester

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Technology Process of Acetic acid (E)-(4S,5R,6S,7R)-4-benzyloxy-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-7-((2S,3R)-3-vinyl-oxiranyl)-hept-2-enyl ester

There total 17 articles about Acetic acid (E)-(4S,5R,6S,7R)-4-benzyloxy-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-7-((2S,3R)-3-vinyl-oxiranyl)-hept-2-enyl 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: 99.0%

: 108-24-7
acetic anhydride

: 182411-50-3
(E)-(4S,5R,6S,7R)-4-Benzyloxy-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-7-((2S,3R)-3-vinyl-oxiranyl)-hept-2-en-1-ol

: 182411-51-4
Acetic acid (E)-(4S,5R,6S,7R)-4-benzyloxy-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-7-((2S,3R)-3-vinyl-oxiranyl)-hept-2-enyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 0.166667h; Ambient temperature;
DOI:10.1016/0040-4020(96)00700-4

Reference yield:

: (3aS,4R,7R,7aS)-7-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ol

: 182411-51-4
Acetic acid (E)-(4S,5R,6S,7R)-4-benzyloxy-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-7-((2S,3R)-3-vinyl-oxiranyl)-hept-2-enyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 67 percent / benzene / 6 h / Heating

2: 69 percent / TfOH / diethyl ether / Ambient temperature

3: 1.) DIBAL, 2.) NaBH₄, CeCl₃ / 1.) dichloromethane, hexane, -78 deg C, 30 min, 2.) MeOH, RT

4: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

5: 100 percent / TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

6: (COCl)2, DMSO / CH₂Cl₂ / 1 h / -78 °C

7: 1.) t-BuOK / 1.) THF, 0 deg C, 1.5 h, 2.) THF, -78 deg C, 30 min

8: PTS*H₂O / ethanol / 25 h / Ambient temperature

9: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

10: 1.) DIBAL_. 2.) NaBH₄, CeCl₃*7H₂O / 1.) CH₂Cl₂, hexane, -78 deg C, 30 min, 2.) MeOH, RT

11: 17 percent / (+)-DET, Ti(Oi-Pr)4, t-BuO₂H / CH₂Cl₂ / 216 h / -25 °C

12: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, 0 deg C, 1.5 h, 2.) THF, 0 deg C, 30 min

13: 99 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

14: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 0.17 h / Ambient temperature

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; diethyl (2R,3R)-tartrate; trifluorormethanesulfonic acid; PTS*H₂O; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; benzene;
DOI:10.1016/0040-4020(96)00700-4

Reference yield:

: (2E,8E)-(4R,5R,6S,7S)-7-Benzyloxy-5,6,10-trihydroxy-4-(4-methoxy-benzyloxy)-deca-2,8-dienoic acid ethyl ester

: 182411-51-4
Acetic acid (E)-(4S,5R,6S,7R)-4-benzyloxy-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-7-((2S,3R)-3-vinyl-oxiranyl)-hept-2-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2: 1.) DIBAL_. 2.) NaBH₄, CeCl₃*7H₂O / 1.) CH₂Cl₂, hexane, -78 deg C, 30 min, 2.) MeOH, RT

3: 17 percent / (+)-DET, Ti(Oi-Pr)4, t-BuO₂H / CH₂Cl₂ / 216 h / -25 °C

4: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, 0 deg C, 1.5 h, 2.) THF, 0 deg C, 30 min

5: 99 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

6: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 0.17 h / Ambient temperature

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; cerium(III) chloride; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0040-4020(96)00700-4