(E)-(4S,6R)-7-Benzyloxy-1-{(2R,3R)-3-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxiranyl}-4-methyl-6-triethylsilanyloxy-hept-1-en-3-one

Base Information

Chemical Name:(E)-(4S,6R)-7-Benzyloxy-1-{(2R,3R)-3-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxiranyl}-4-methyl-6-triethylsilanyloxy-hept-1-en-3-one
CAS No.:388082-03-9
Molecular Formula:C₄₂H₆₈O₇Si₂
Molecular Weight:741.169
Hs Code.:

(E)-(4S,6R)-7-Benzyloxy-1-{(2R,3R)-3-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxiranyl}-4-methyl-6-triethylsilanyloxy-hept-1-en-3-one

Synonyms:(E)-(4S,6R)-7-Benzyloxy-1-{(2R,3R)-3-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxiranyl}-4-methyl-6-triethylsilanyloxy-hept-1-en-3-one

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Chemical Property of (E)-(4S,6R)-7-Benzyloxy-1-{(2R,3R)-3-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxiranyl}-4-methyl-6-triethylsilanyloxy-hept-1-en-3-one

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Technology Process of (E)-(4S,6R)-7-Benzyloxy-1-{(2R,3R)-3-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxiranyl}-4-methyl-6-triethylsilanyloxy-hept-1-en-3-one

There total 14 articles about (E)-(4S,6R)-7-Benzyloxy-1-{(2R,3R)-3-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxiranyl}-4-methyl-6-triethylsilanyloxy-hept-1-en-3-one 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: 92.0%

: 388082-00-6
(2S,3R)-3-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxirane-2-carbaldehyde

: 388081-99-0
((3S,5R)-6-Benzyloxy-3-methyl-2-oxo-5-triethylsilanyloxy-hexyl)-phosphonic acid dimethyl ester

: 388082-03-9
(E)-(4S,6R)-7-Benzyloxy-1-{(2R,3R)-3-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxiranyl}-4-methyl-6-triethylsilanyloxy-hept-1-en-3-one

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -20 ℃; for 2h;
DOI:10.1021/ol016948v

Reference yield:

: 994-30-9
triethylsilyl chloride

: 388082-03-9
(E)-(4S,6R)-7-Benzyloxy-1-{(2R,3R)-3-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxiranyl}-4-methyl-6-triethylsilanyloxy-hept-1-en-3-one

Guidance literature:: Multi-step reaction with 2 steps

1: -78 - 20 °C

2: 92 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene / 2 h / -20 °C

With potassium hexamethylsilazane; In tetrahydrofuran; toluene; 2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol016948v

Reference yield:

: 80910-01-6,108836-41-5,134733-19-0,144069-33-0
(S)-2-[(4-methoxybenzyloxy)methyl]oxirane

: 388082-03-9
(E)-(4S,6R)-7-Benzyloxy-1-{(2R,3R)-3-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxiranyl}-4-methyl-6-triethylsilanyloxy-hept-1-en-3-one

Guidance literature:: Multi-step reaction with 9 steps

1: CuI

2: imidazole

3: OsO₄; NMO

4: NaIO₄

5: DIBAL / -78 °C

6: 90 percent / Ti(O-i-Pr)4; (-)-DET; TBHP / -40 °C

7: 91 percent / Swern reagent

8: 92 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene / 2 h / -20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; N-methyl-2-indolinone; swern reagent; potassium hexamethylsilazane; diisobutylaluminium hydride; (-)-diethyl tartrate; In tetrahydrofuran; toluene; 7: Sharpless asymmetric epoxidation / 8: Swern oxidation / 9: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol016948v