[(2S,6S)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-3-oxo-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester

Base Information

Chemical Name:[(2S,6S)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-3-oxo-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester
CAS No.:206255-45-0
Molecular Formula:C₃₈H₅₆O₉Si
Molecular Weight:684.943
Hs Code.:

[(2S,6S)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-3-oxo-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester

Synonyms:[(2S,6S)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-3-oxo-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester

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Chemical Property of [(2S,6S)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-3-oxo-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester

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Technology Process of [(2S,6S)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-3-oxo-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester

There total 10 articles about [(2S,6S)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-3-oxo-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl 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:

: {(2S,6S)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-3-oxo-tetrahydro-pyran-4-yl}-methanesulfonyloxy-acetic acid methyl ester

: 206255-45-0
[(2S,6S)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-3-oxo-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; Yield given; Ambient temperature;
DOI:10.1021/ja9727631

Reference yield:

: 206255-40-5
6-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-hexane-2,4-dione

: 206255-45-0
[(2S,6S)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-3-oxo-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) LDA, 3.) p-TsOH

2: NaBH₄, CeCl₃*7H₂O / methanol / -20 °C

3: m-CPBA, NaHCO₃ / CH₂Cl₂

4: DMAP / CH₂Cl₂ / -10 °C

5: Dess-Martin periodinane / Ambient temperature

6: 95 percent / SmI₂ / tetrahydrofuran; methanol / -78 °C

7: 90 percent / LDA / tetrahydrofuran / -78 °C

8: Et₃N / CH₂Cl₂ / -10 °C

9: DBU / tetrahydrofuran / Ambient temperature

With dmap; sodium tetrahydroborate; samarium diiodide; cerium(III) chloride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja9727631

Reference yield:

: 206255-41-6
(3R,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-pentanal

: 206255-45-0
[(2S,6S)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-3-oxo-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) LDA, 3.) p-TsOH

2: NaBH₄, CeCl₃*7H₂O / methanol / -20 °C

3: m-CPBA, NaHCO₃ / CH₂Cl₂

4: DMAP / CH₂Cl₂ / -10 °C

5: Dess-Martin periodinane / Ambient temperature

6: 95 percent / SmI₂ / tetrahydrofuran; methanol / -78 °C

7: 90 percent / LDA / tetrahydrofuran / -78 °C

8: Et₃N / CH₂Cl₂ / -10 °C

9: DBU / tetrahydrofuran / Ambient temperature

With dmap; sodium tetrahydroborate; samarium diiodide; cerium(III) chloride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja9727631