Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-{(S)-2-amino-3-[(S)-2-(4-nitro-phenylcarbamoyl)-pyrrolidin-1-yl]-3-oxo-propoxy}-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-{(S)-2-amino-3-[(S)-2-(4-nitro-phenylcarbamoyl)-pyrrolidin-1-yl]-3-oxo-propoxy}-tetrahydro-pyran-4-yl ester
• CAS No.: 175854-14-5
• Molecular Formula: C₂₈H₃₆N₄O₁₄
• Molecular Weight: 652.612

Synonyms:

Chemical Property of Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-{(S)-2-amino-3-[(S)-2-(4-nitro-phenylcarbamoyl)-pyrrolidin-1-yl]-3-oxo-propoxy}-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-{(S)-2-amino-3-[(S)-2-(4-nitro-phenylcarbamoyl)-pyrrolidin-1-yl]-3-oxo-propoxy}-tetrahydro-pyran-4-yl ester

There total 2 articles about Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-{(S)-2-amino-3-[(S)-2-(4-nitro-phenylcarbamoyl)-pyrrolidin-1-yl]-3-oxo-propoxy}-tetrahydro-pyran-4-yl 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:

β-D-glucose pentaacetate (604-69-3) → Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-{(S)-2-amino-3-[(S)-2-(4-nitro-phenylcarbamoyl)-pyrrolidin-1-yl]-3-oxo-propoxy}-tetrahydro-pyran-4-yl ester (175854-14-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 35 percent / BF₃*Et₂O / acetonitrile / 2 h / Ambient temperature

2: 1.) DppCl, NMM

3: morpholine

With morpholine; 4-methyl-morpholine; boron trifluoride diethyl etherate; In acetonitrile;

DOI:10.1039/cc9960000313

Reference yield:

Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(S)-2-(4-nitro-phenylcarbamoyl)-pyrrolidin-1-yl]-3-oxo-propoxy}-tetrahydro-pyran-3-yl ester (175854-13-4) → Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-{(S)-2-amino-3-[(S)-2-(4-nitro-phenylcarbamoyl)-pyrrolidin-1-yl]-3-oxo-propoxy}-tetrahydro-pyran-4-yl ester (175854-14-5)

Guidance literature:

With morpholine;

DOI:10.1039/cc9960000313

Reference yield:

Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-{(S)-2-amino-3-[(S)-2-(4-nitro-phenylcarbamoyl)-pyrrolidin-1-yl]-3-oxo-propoxy}-tetrahydro-pyran-4-yl ester (175854-14-5) → (S)-1-[(S)-2-Amino-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propionyl]-pyrrolidine-2-carboxylic acid (4-nitro-phenyl)-amide

Guidance literature:

With sodium methylate; In methanol; Yield given;

DOI:10.1039/cc9960000313

upstream raw materials:

Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(S)-2-(4-nitro-phenylcarbamoyl)-pyrrolidin-1-yl]-3-oxo-propoxy}-tetrahydro-pyran-3-yl ester

β-D-glucose pentaacetate

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