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

Base Information

Chemical Name:methyl 3-benzyloxy-4-[(2S)-2-[(2R,3R)-3-hydroxymethyloxiran-2-yl]-2-triisopropylsilyloxyethyl]-5-nitrobenzoate
CAS No.:503311-45-3
Molecular Formula:C₂₉H₄₁NO₈Si
Molecular Weight:559.732
Hs Code.:

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

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

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

There total 12 articles about methyl 3-benzyloxy-4-[(2S)-2-[(2R,3R)-3-hydroxymethyloxiran-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:

: 503311-44-2
methyl 3-benzyloxy-4-[(2S)-2-[(2R,3R)-3-(tert-butyldimethylsilyloxymethyl)oxiran-2-yl]-2-triisopropylsilyloxyethyl]-5-nitrobenzoate

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

Guidance literature:: With (1S)-10-camphorsulfonic acid; In methanol; at 20 ℃; for 1h;
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

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

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

: 503867-75-2
methyl 3-benzyloxy-4-[(2S,3R,4S)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-4-(toluene-4-sulfonyl)oxy-2-triisopropylsilyloxypentyl]-5-nitrobenzoate

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

Guidance literature:: Multi-step reaction with 2 steps

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

2: CSA / methanol / 1 h / 20 °C

With camphor-10-sulfonic acid; sodium hydride; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo049862z