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

Base Information

Chemical Name:methyl 3-benzyloxy-4-{(2S)-2-[(4S,5S)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethyl}-5-nitrobenzoate
CAS No.:503311-52-2
Molecular Formula:C₂₉H₄₁NO₉Si
Molecular Weight:575.731
Hs Code.:

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

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Chemical Property of methyl 3-benzyloxy-4-{(2S)-2-[(4S,5S)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethyl}-5-nitrobenzoate

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Technology Process of methyl 3-benzyloxy-4-{(2S)-2-[(4S,5S)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethyl}-5-nitrobenzoate

There total 5 articles about methyl 3-benzyloxy-4-{(2S)-2-[(4S,5S)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethyl}-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: 94.0%

: 503311-39-5
3-Benzyloxy-4-{2-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-5-nitro-benzoic acid methyl ester

: 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

: 3-Benzyloxy-4-{(R)-2-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl}-5-nitro-benzoic acid methyl ester

Guidance literature:: With zinc(II) tetrahydroborate; In diethyl ether; at -30 ℃; for 3h;
DOI:10.1002/anie.200290016

Reference yield:

: 438547-22-9
3-Benzyloxy-5-nitro-4-trifluoromethanesulfonyloxy-benzoic acid methyl ester

: 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

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / Pd(OAc)2; PPh₃; Et₃N / tetrahydrofuran / 13 h / 20 - 65 °C

2: benzene / 1 h / 20 °C

3: aq. AcOH / 2 h / 20 °C

4: 94 percent / Zn(BH₄)2 / diethyl ether / 3 h / -30 °C

With palladium diacetate; zinc(II) tetrahydroborate; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; benzene; 1: Sonogashira coupling;
DOI:10.1002/anie.200290016

Reference yield:

: 360562-49-8
5-[(tert-Butyldimethylsilyl)oxy]-1,2-dideoxy-3,4-O-(1-methylethylidene)-L-threo-pent-1-yne

: 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

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / Pd(OAc)2; PPh₃; Et₃N / tetrahydrofuran / 13 h / 20 - 65 °C

2: benzene / 1 h / 20 °C

3: aq. AcOH / 2 h / 20 °C

4: 94 percent / Zn(BH₄)2 / diethyl ether / 3 h / -30 °C

With palladium diacetate; zinc(II) tetrahydroborate; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; benzene; 1: Sonogashira coupling;
DOI:10.1002/anie.200290016