(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-(benzyloxy)phenyl)-1-(benzyl-oxycarbonyl)pyrrolidine-3,4-diyl diacetate

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-(benzyloxy)phenyl)-1-(benzyl-oxycarbonyl)pyrrolidine-3,4-diyl diacetate
• CAS No.: 1346680-28-1
• Molecular Formula: C₃₂H₃₃NO₉
• Molecular Weight: 575.615

Synonyms:(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-(benzyloxy)phenyl)-1-(benzyl-oxycarbonyl)pyrrolidine-3,4-diyl diacetate

Chemical Property of (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-(benzyloxy)phenyl)-1-(benzyl-oxycarbonyl)pyrrolidine-3,4-diyl diacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-(benzyloxy)phenyl)-1-(benzyl-oxycarbonyl)pyrrolidine-3,4-diyl diacetate

There total 19 articles about (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-(benzyloxy)phenyl)-1-(benzyl-oxycarbonyl)pyrrolidine-3,4-diyl diacetate 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: 90.0%

(1S,2R,3R,4R)-1-(4-(benzyloxy)phenyl)-4-(benzyloxycarbonylamino)pentane-1,2,3,5-tetrayl tetraacetate (1346680-25-8) → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-(benzyloxy)phenyl)-1-(benzyl-oxycarbonyl)pyrrolidine-3,4-diyl diacetate (1346680-28-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 4.08333h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.09.043

Reference yield: 82.0%

(2R,3R,4R)-5-(4-(benzyloxy)phenyl)-2-(benzyloxycarbonylamino)-pentane-1,3,4-triyl triacetate → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-(benzyloxy)phenyl)-1-(benzyl-oxycarbonyl)pyrrolidine-3,4-diyl diacetate (1346680-28-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In acetonitrile; at 80 ℃; for 4h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.5b02275

Reference yield:

(4R,5S)-ethyl 5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate (1346679-74-0) → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-(benzyloxy)phenyl)-1-(benzyl-oxycarbonyl)pyrrolidine-3,4-diyl diacetate (1346680-28-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.33 h / 0 - 20 °C / Inert atmosphere

1.2: 2 h / 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.67 h / -78 °C / Inert atmosphere

2.2: -78 - 0 °C / Inert atmosphere

3.1: toluene / 6 h / Inert atmosphere; Reflux

4.1: osmium(VIII) oxide; water; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III) / tert-butyl alcohol / 24.08 h / 0 °C / Inert atmosphere

5.1: thionyl chloride; triethylamine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

6.1: sodium azide / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere

6.2: 20 °C / Inert atmosphere; Cooling with ice

7.1: ethanol; triphenylphosphine / 6 h / 0 - 20 °C / Inert atmosphere

8.1: sodium carbonate / ethanol / 8 h / 0 - 20 °C / Inert atmosphere

9.1: sodium tetrahydroborate; lithium chloride / tetrahydrofuran; ethanol / 3.33 h / 0 - 20 °C / Inert atmosphere

10.1: water; acetic acid / 8 h / 20 °C / Inert atmosphere

11.1: dmap / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

12.1: trifluoroacetic acid / dichloromethane / 4.08 h / 0 - 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; thionyl chloride; sodium azide; oxalyl dichloride; ethanol; water; sodium carbonate; potassium carbonate; acetic acid; dimethyl sulfoxide; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium chloride; potassium hexacyanoferrate(III); In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Wittig reaction;

DOI:10.1016/j.tetlet.2011.09.043

upstream raw materials:

p-benzyloxybenzaldehyde

(4R,5S)-ethyl 5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol

(E)-ethyl 3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

Downstream raw materials:

(2R,3R,4R,5R)-4-(hydroxy)-2-(hydroxymethyl)-5-(4-hydroxyphenyl)pyrrolidin-3-ol

(5R,6R,7R,7αR)-5-(4-(benzyloxy)phenyl)-6,7-dihydroxytetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

(5R,6R,7R,7aR)-6,7-dihydroxy-5-(4-hydroxyphenyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 1346680-28-1 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-(benzyloxy)phenyl)-1-(benzyl-oxycarbonyl)pyrrolidine-3,4-diyl diacetate

Send

Send

Metric Ton KG G Pound L ML

Send

Send