L-allo-1-(benzyloxycarbonyl)-4-((4-ooazetidin-2-yl)oxy)proline diphenylmethyl ester

Base Information

• Chemical Name: L-allo-1-(benzyloxycarbonyl)-4-((4-ooazetidin-2-yl)oxy)proline diphenylmethyl ester
• CAS No.: 97551-75-2
• Molecular Formula: C₂₉H₂₈N₂O₆
• Molecular Weight: 500.551

Synonyms:

Chemical Property of L-allo-1-(benzyloxycarbonyl)-4-((4-ooazetidin-2-yl)oxy)proline diphenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-allo-1-(benzyloxycarbonyl)-4-((4-ooazetidin-2-yl)oxy)proline diphenylmethyl ester

There total 16 articles about L-allo-1-(benzyloxycarbonyl)-4-((4-ooazetidin-2-yl)oxy)proline diphenylmethyl 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: 50.0%

N-(benzyloxycarbonyl)-5-bromo-4-(4-oxo-2-azetidinyloxy)-D-threo-L-norvaline diphenylmethyl ester (97569-85-2) → L-allo-1-(benzyloxycarbonyl)-4-((4-ooazetidin-2-yl)oxy)proline diphenylmethyl ester (97551-75-2,97590-62-0) + 3-<(3S,5R)-7-oxo-1-aza-4-oxabicyclo<3.2.0>hept-3-yl>-N-(benzyloxycarbonyl)-L-alanine diphenylmethyl ester (97590-61-9) + 3-<(3S,5S)-7-oxo-1-aza-4-oxabicyclo<3.2.0>hept-3-yl>-N-(benzyloxycarbonyl)-L-alanine diphenylmethyl ester (97551-74-1)

Guidance literature:

With 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octadienoate; In N,N-dimethyl-formamide; at 70 ℃; for 10h;

DOI:10.1021/jo00219a008

Reference yield:

5-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose (80244-96-8) → L-allo-1-(benzyloxycarbonyl)-4-((4-ooazetidin-2-yl)oxy)proline diphenylmethyl ester (97551-75-2,97590-62-0)

Guidance literature:

Multi-step reaction with 15 steps

1: 97.3 percent / 1,2-dichloro-ethane / 1 h / Heating

2: 95 percent / Bu3SnH, α,α'-azobis(isobutyronitrile) (AIBN) / toluene / 1 h / Heating

3: 60.9 percent / trifluoroacetic acid (TFA) / 1.25 h / 5 °C

4: 1.) dibutyltin oxide, 2.) Et₃N / 1.) MeOH, reflux, 1.5 h, 2.) 1,2-dimethoxyethane, 4 deg C, 1 h

5: 98 percent / RuO₄ / 1,2-dichloro-ethane / 1 h / 4 - 20 °C

6: 90.1 percent / LiN₃ / dimethylformamide / Ambient temperature

7: 51 percent / H₂, HCl / 10percent Pd/C / ethanol / 0.75 h / 760 Torr

8: 90.5 percent / NaHCO₃ / H₂O; diethyl ether / 2.5 h / 4 - 20 °C

9: 93.4 percent / Dowex AG 50W-X₄ (H⁺) / dioxane; H₂O / 24 h / 73 - 75 °C

10: 1.) 0.1 N aq. KOH, 2.) Dowex AG 50W-X₄ (H⁺) / 1.) 20 deg C, 1 h

11: 78.3 percent / methyl acetate / 4 h / Ambient temperature

12: 62.6 percent / pyridine, 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 1.) -10 deg C, 5 h, 2.) RT, 15 h

13: 51.5 percent / Pd(OAc)2, NEt₃ / benzene / 38 h / Ambient temperature

14: 94.9 percent / LiBr / tetrahydrofuran / 6.5 h / Heating

15: 35.2 percent / 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octadienoate / dimethylformamide / 10 h / 70 °C

With pyridine; hydrogenchloride; dmap; palladium diacetate; potassium hydroxide; ruthenium tetroxide; lithium azide; 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octadienoate; Dowex AG 50W-X₄ (H⁺); azobisisobutyronitrile; hydrogen; tri-n-butyl-tin hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; acetic acid methyl ester; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00219a008

Reference yield:

1,2-O-isopropylidene-α-D-xylose (20031-21-4) → L-allo-1-(benzyloxycarbonyl)-4-((4-ooazetidin-2-yl)oxy)proline diphenylmethyl ester (97551-75-2,97590-62-0)

Guidance literature:

Multi-step reaction with 16 steps

1: 85.1 percent / pyridine / CH₂Cl₂ / Ambient temperature

2: 97.3 percent / 1,2-dichloro-ethane / 1 h / Heating

3: 95 percent / Bu3SnH, α,α'-azobis(isobutyronitrile) (AIBN) / toluene / 1 h / Heating

4: 60.9 percent / trifluoroacetic acid (TFA) / 1.25 h / 5 °C

5: 1.) dibutyltin oxide, 2.) Et₃N / 1.) MeOH, reflux, 1.5 h, 2.) 1,2-dimethoxyethane, 4 deg C, 1 h

6: 98 percent / RuO₄ / 1,2-dichloro-ethane / 1 h / 4 - 20 °C

7: 90.1 percent / LiN₃ / dimethylformamide / Ambient temperature

8: 51 percent / H₂, HCl / 10percent Pd/C / ethanol / 0.75 h / 760 Torr

9: 90.5 percent / NaHCO₃ / H₂O; diethyl ether / 2.5 h / 4 - 20 °C

10: 93.4 percent / Dowex AG 50W-X₄ (H⁺) / dioxane; H₂O / 24 h / 73 - 75 °C

11: 1.) 0.1 N aq. KOH, 2.) Dowex AG 50W-X₄ (H⁺) / 1.) 20 deg C, 1 h

12: 78.3 percent / methyl acetate / 4 h / Ambient temperature

13: 62.6 percent / pyridine, 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 1.) -10 deg C, 5 h, 2.) RT, 15 h

14: 51.5 percent / Pd(OAc)2, NEt₃ / benzene / 38 h / Ambient temperature

15: 94.9 percent / LiBr / tetrahydrofuran / 6.5 h / Heating

16: 35.2 percent / 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octadienoate / dimethylformamide / 10 h / 70 °C

With pyridine; hydrogenchloride; dmap; palladium diacetate; potassium hydroxide; ruthenium tetroxide; lithium azide; 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octadienoate; Dowex AG 50W-X₄ (H⁺); azobisisobutyronitrile; hydrogen; tri-n-butyl-tin hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; acetic acid methyl ester; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00219a008

upstream raw materials:

N-(benzyloxycarbonyl)-5-bromo-4-(4-oxo-2-azetidinyloxy)-D-threo-L-norvaline diphenylmethyl ester

5-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose

(3S,5S)-3-benzyloxycarbonylamino-5-hydroxy-γ-lactone

1,2-O-isopropylidene-α-D-xylose

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