(4R)-4-[(4'R)-1'-O-acetyl-2',3'-O-isopropylidene-L-erythrofuranos-4'-yl]-2-phenylamino-2-oxazoline

Base Information

Chemical Name:(4R)-4-[(4'R)-1'-O-acetyl-2',3'-O-isopropylidene-L-erythrofuranos-4'-yl]-2-phenylamino-2-oxazoline
CAS No.:630390-63-5
Molecular Formula:C₁₈H₂₂N₂O₆
Molecular Weight:362.382
Hs Code.:

Synonyms:(4R)-4-[(4'R)-1'-O-acetyl-2',3'-O-isopropylidene-L-erythrofuranos-4'-yl]-2-phenylamino-2-oxazoline

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Chemical Property of (4R)-4-[(4'R)-1'-O-acetyl-2',3'-O-isopropylidene-L-erythrofuranos-4'-yl]-2-phenylamino-2-oxazoline

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Technology Process of (4R)-4-[(4'R)-1'-O-acetyl-2',3'-O-isopropylidene-L-erythrofuranos-4'-yl]-2-phenylamino-2-oxazoline

There total 10 articles about (4R)-4-[(4'R)-1'-O-acetyl-2',3'-O-isopropylidene-L-erythrofuranos-4'-yl]-2-phenylamino-2-oxazoline 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: 72.0%

: 1-O-acetyl-5-deoxy-2,3-O-isopropylidene-5-(3-phenylcarbodiimido)-6-O-trimethylsilyl-α-D-mannofuranose

: 630390-63-5
(4R)-4-[(4'R)-1'-O-acetyl-2',3'-O-isopropylidene-L-erythrofuranos-4'-yl]-2-phenylamino-2-oxazoline

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃;
DOI:10.1021/jo034673m

Reference yield:

: 7306-64-1
2,3:5,6-di-O-isopropylidene-L-gulonolactone

: 630390-63-5
(4R)-4-[(4'R)-1'-O-acetyl-2',3'-O-isopropylidene-L-erythrofuranos-4'-yl]-2-phenylamino-2-oxazoline

Guidance literature:: Multi-step reaction with 10 steps

1: 75 percent / DIBAL / toluene; hexane / 2 h / -78 - 20 °C

2: 75 percent / pyridine

3: 80 percent / aq. AcOH / 2 h / 40 °C

4: 72 percent / pyridine / 36 h / 20 °C

5: pyridine / CH₂Cl₂ / 1 h / -25 - 25 °C

6: 1.87 g / NaN₃ / dimethylformamide / 18 h / 20 °C

7: 75 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / 0 - 20 °C

8: 80 percent / HMDS; pyridine / 2 h / 20 °C

9: 70 percent / PPh₃ / toluene / 24 h / 20 °C

10: 72 percent / TBAF / tetrahydrofuran / 0 °C

With pyridine; sodium azide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; acetic acid; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo034673m

Reference yield:

: 94842-76-9
2,3:5,6-di-O-isopropylidene-α-D-mannofuranose

: 630390-63-5
(4R)-4-[(4'R)-1'-O-acetyl-2',3'-O-isopropylidene-L-erythrofuranos-4'-yl]-2-phenylamino-2-oxazoline

Guidance literature:: Multi-step reaction with 9 steps

1: 75 percent / pyridine

2: 80 percent / aq. AcOH / 2 h / 40 °C

3: 72 percent / pyridine / 36 h / 20 °C

4: pyridine / CH₂Cl₂ / 1 h / -25 - 25 °C

5: 1.87 g / NaN₃ / dimethylformamide / 18 h / 20 °C

6: 75 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / 0 - 20 °C

7: 80 percent / HMDS; pyridine / 2 h / 20 °C

8: 70 percent / PPh₃ / toluene / 24 h / 20 °C

9: 72 percent / TBAF / tetrahydrofuran / 0 °C

With pyridine; sodium azide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo034673m