(2S,3S,4R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester

Base Information

Chemical Name:(2S,3S,4R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester
CAS No.:778640-43-0
Molecular Formula:C₂₉H₄₃NO₉
Molecular Weight:549.662
Hs Code.:

(2S,3S,4R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester

Synonyms:(2S,3S,4R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester

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Chemical Property of (2S,3S,4R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester

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Technology Process of (2S,3S,4R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester

There total 8 articles about (2S,3S,4R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic 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:

: 778640-58-7
(R)-4-((R)-{(4S,5S)-5-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-4-methoxycarbonyl-2,2-dimethyl-[1,3]dioxolan-4-yl}-methylsulfanylthiocarboxyoxy-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 778640-43-0
(2S,3S,4R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 1h; Heating;
DOI:10.1002/anie.200454192

Reference yield:

: 95715-87-0
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

: 778640-43-0
(2S,3S,4R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

1.2: 69 percent / tetrahydrofuran / 4 h / -78 °C

2.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

2.2: tetrahydrofuran / 0.33 h / 0 °C

2.3: tetrahydrofuran / 0.5 h / 0 - 20 °C

3.1: 475 mg / n-Bu₃SnH; AIBN / toluene / 1 h / Heating

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hexamethyldisilazane; In tetrahydrofuran; toluene;
DOI:10.1055/s-2007-965893

Reference yield:

: 778640-51-0
(2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenal

: 778640-43-0
(2S,3S,4R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaClO₂; NaH₂PO₄ / dimethylsulfoxide; H₂O / 1 h / 20 °C

2.1: 2.61 g / diethyl ether; methanol / 0.5 h / 20 °C

3.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

3.2: 69 percent / tetrahydrofuran / 4 h / -78 °C

4.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

4.2: tetrahydrofuran / 0.33 h / 0 °C

4.3: tetrahydrofuran / 0.5 h / 0 - 20 °C

5.1: 475 mg / n-Bu₃SnH; AIBN / toluene / 1 h / Heating

With sodium chlorite; sodium dihydrogenphosphate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; water; dimethyl sulfoxide; toluene;
DOI:10.1055/s-2007-965893