(S)-2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

Base Information

• Chemical Name: (S)-2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester
• CAS No.: 59534-95-1
• Molecular Formula: C₂₉H₃₂N₂O₁₀
• Molecular Weight: 568.58

Synonyms:

Chemical Property of (S)-2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of (S)-2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

There total 2 articles about (S)-2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 2,5-dioxo-pyrrolidin-1-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:

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-carboxyethyl>-α-D-glucopyranoside (2862-03-5) → 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramic acid N-hydroxysuccinimide ester (59534-95-1)

Guidance literature:

With dicyclohexyl-carbodiimide; In 1,4-dioxane; for 3h;

Reference yield:

→ 2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester (59534-95-1)

Guidance literature:

Glucopyranosid 5, N-Hydroxysuccinimid, Dicyclohexylcarbodiimid;

DOI:10.1246/bcsj.49.533

Reference yield: 74.0%

alanyl-D-isoglutaminyl-Nε-acetyllysyl-D-alanine amide (72490-74-5) + 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramic acid N-hydroxysuccinimide ester (59534-95-1) → 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramyl-alanyl-D-isoglutaminyl-Nε-acetyllysyl-D-alanine amide (68197-47-7)

Guidance literature:

In tetrahydrofuran; N,N-dimethyl-formamide; 1. 0 deg C, 2 h; 2. room temperature, 24 h;

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-carboxyethyl>-α-D-glucopyranoside

Downstream raw materials:

1-O-benzyl-4,6-O-benzylidene-N-acetylmuramyl-alanyl-D-isoglutaminyl-N^ε-acetyllysyl-D-alanine amide

1-O-benzyl-4,6-O-benzylidene-N-acetylmuramyl-alanyl-D-isoglutaminyl-N^ε-acetyllysyl-D-alanyl-pentaglycine amide

BBM-L-Ala-D-iGln-L-Lys(Tos)-D-Ala-(L-Ala)2-OMe

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