methyl 3-benzyloxy-4-[(2S)-2-[(2R,3R)-3-formyloxiran-2-yl]-2-triisopropylsilyloxyethyl]-5-nitrobenzoate

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Chemical Name:methyl 3-benzyloxy-4-[(2S)-2-[(2R,3R)-3-formyloxiran-2-yl]-2-triisopropylsilyloxyethyl]-5-nitrobenzoate
CAS No.:503867-76-3
Molecular Formula:C₂₉H₃₉NO₈Si
Molecular Weight:557.716
Hs Code.:

Synonyms:methyl 3-benzyloxy-4-[(2S)-2-[(2R,3R)-3-formyloxiran-2-yl]-2-triisopropylsilyloxyethyl]-5-nitrobenzoate

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Chemical Property of methyl 3-benzyloxy-4-[(2S)-2-[(2R,3R)-3-formyloxiran-2-yl]-2-triisopropylsilyloxyethyl]-5-nitrobenzoate

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Technology Process of methyl 3-benzyloxy-4-[(2S)-2-[(2R,3R)-3-formyloxiran-2-yl]-2-triisopropylsilyloxyethyl]-5-nitrobenzoate

There total 13 articles about methyl 3-benzyloxy-4-[(2S)-2-[(2R,3R)-3-formyloxiran-2-yl]-2-triisopropylsilyloxyethyl]-5-nitrobenzoate 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:

: 503311-45-3
methyl 3-benzyloxy-4-[(2S)-2-[(2R,3R)-3-hydroxymethyloxiran-2-yl]-2-triisopropylsilyloxyethyl]-5-nitrobenzoate

: 503867-76-3
methyl 3-benzyloxy-4-[(2S)-2-[(2R,3R)-3-formyloxiran-2-yl]-2-triisopropylsilyloxyethyl]-5-nitrobenzoate

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 0.5h;
DOI:10.1002/anie.200290016

Reference yield:

: 503311-52-2
methyl 3-benzyloxy-4-{(2S)-2-[(4S,5S)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethyl}-5-nitrobenzoate

: 503867-76-3
methyl 3-benzyloxy-4-[(2S)-2-[(2R,3R)-3-formyloxiran-2-yl]-2-triisopropylsilyloxyethyl]-5-nitrobenzoate

Guidance literature:: Multi-step reaction with 7 steps

1: 2,6-lutidine / CH₂Cl₂ / 7 h / 20 °C

2: 3.37 g / aq. AcOH / 4 h / 100 °C

3: Et₃N; DMAP / CH₂Cl₂ / 13 h / 20 °C

4: DABCO / CH₂Cl₂ / 1.5 h / 20 °C

5: 2.82 g / NaH / dimethylformamide / 1 h / 20 °C

6: CSA / methanol / 1 h / 20 °C

7: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 - 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; dmap; camphor-10-sulfonic acid; sodium hydride; Dess-Martin periodane; acetic acid; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo049862z

Reference yield:

: 503867-74-1
methyl 3-benzyloxy-4-[(2S,3R,4S)-5-(tert-butyldimethylsilyloxy)-3,4-dihydroxy-2-triisopropylsilyloxypentyl]-5-nitrobenzoate

: 503867-76-3
methyl 3-benzyloxy-4-[(2S)-2-[(2R,3R)-3-formyloxiran-2-yl]-2-triisopropylsilyloxyethyl]-5-nitrobenzoate

Guidance literature:: Multi-step reaction with 4 steps

1: DABCO / CH₂Cl₂ / 1.5 h / 20 °C

2: 2.82 g / NaH / dimethylformamide / 1 h / 20 °C

3: CSA / methanol / 1 h / 20 °C

4: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 - 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; camphor-10-sulfonic acid; sodium hydride; Dess-Martin periodane; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo049862z