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

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-hexenal
• CAS No.: 778640-52-1
• Molecular Formula: C₂₈H₄₁NO₈
• Molecular Weight: 519.635

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

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-hexenal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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-hexenal

There total 9 articles about (2S,3S,4R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenal 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: 88.0%

(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 (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-hexenal (778640-52-1)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -100 ℃; for 1h;

DOI:10.1002/anie.200454192

Reference yield:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) → (2S,3S,4R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenal (778640-52-1)

Guidance literature:

Multi-step reaction with 4 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

4.1: 88 percent / DIBAL-H / toluene; CH₂Cl₂ / 1 h / -100 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1055/s-2007-965893

Reference yield:

(2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenal (778640-51-0) → (2S,3S,4R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenal (778640-52-1)

Guidance literature:

Multi-step reaction with 6 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

6.1: 88 percent / DIBAL-H / toluene; CH₂Cl₂ / 1 h / -100 °C

With sodium chlorite; sodium dihydrogenphosphate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene;

DOI:10.1055/s-2007-965893

upstream raw materials:

(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

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenal

(2R,3S,4R)-2,3-O-isopropylidene-4-(p-methoxybenzyloxy)-5-hexene-1,2,3-triol

Downstream raw materials:

(1S,2R,3R,6R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-6-(p-methoxybenzyloxy)-4-cyclohexene-1,2,3-triol

(1S,2S,3R,6R)-6-(tert-butyldimethylsiloxy)-1-[(2S)-2-(tert-butoxycarbonylamino)-3-hydroxypropyl]-1,2-O-isopropylidene-3-(p-methoxybenzyloxy)-4-cyclohexene-1,2-diol

(1S,2S,3R,6R)-6-(tert-butyldimethylsiloxy)-1-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-3-(p-methoxybenzyloxy)-4-cyclohexene-1,2-diol

(3R,4R,5S,6R)-4-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-4,5-O-isopropylidene-6-(p-methoxybenzyloxy)-1,7-octadiene-3,4,5-triol

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