(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

Base Information

• Chemical Name: (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
• CAS No.: 778640-37-2
• Molecular Formula: C₃₀H₄₅NO₈
• Molecular Weight: 547.689

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (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

There total 10 articles about (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 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: 93.0%

vinyl magnesium bromide (1826-67-1) + (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) → (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 (778640-37-2)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1002/anie.200454192

Reference yield:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) → (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 (778640-37-2)

Guidance literature:

Multi-step reaction with 5 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

5.1: 93 percent / tetrahydrofuran / 1 h / 0 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene; 5.1: Grignard reaction;

DOI:10.1055/s-2007-965893

Reference yield:

(2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenal (778640-51-0) → (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 (778640-37-2)

Guidance literature:

Multi-step reaction with 7 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

7.1: 93 percent / tetrahydrofuran / 1 h / 0 °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; 7.1: Grignard reaction;

DOI:10.1055/s-2007-965893

upstream raw materials:

vinyl magnesium bromide

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

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

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

Downstream raw materials:

(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

(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

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