{[2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-acetyl]-[2-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethyl]-amino}-acetic acid benzyl ester

Base Information

• Chemical Name: {[2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-acetyl]-[2-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethyl]-amino}-acetic acid benzyl ester
• CAS No.: 193156-92-2
• Molecular Formula: C₄₁H₅₃NO₂₁
• Molecular Weight: 895.866

Synonyms:{[2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-acetyl]-[2-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethyl]-amino}-acetic acid benzyl ester

Chemical Property of {[2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-acetyl]-[2-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethyl]-amino}-acetic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of {[2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-acetyl]-[2-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethyl]-amino}-acetic acid benzyl ester

There total 5 articles about {[2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-acetyl]-[2-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethyl]-amino}-acetic acid benzyl 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: 80.0%

2-(2,3,4,6-tetra-O-acetylated-1-deoxy-α-D-galactopyranosyl)-ethanoic acid (193156-89-7) + [2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethylamino]-acetic acid benzyl ester (193156-91-1) → {[2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-acetyl]-[2-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethyl]-amino}-acetic acid benzyl ester (193156-92-2)

Guidance literature:

With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1016/S0960-894X(97)00255-2

Reference yield:

2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)acetaldehyde (193156-88-6) → {[2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-acetyl]-[2-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethyl]-amino}-acetic acid benzyl ester (193156-92-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / NaB(OAc)3H; AcOH / tetrahydrofuran / 12 h / 0 - 20 °C / pH 5.0

2: 80 percent / DCC; HOBt; DIEA / CH₂Cl₂ / 16 h / 20 °C

With sodium tris(acetoxy)borohydride; benzotriazol-1-ol; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 1: Addition / 2: Acylation;

DOI:10.1016/S0968-0896(99)00226-6

Reference yield:

allyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside (53263-18-6,82659-53-8,98920-46-8,98920-48-0,98920-49-1,103773-87-1,98920-44-6) → {[2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-acetyl]-[2-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethyl]-amino}-acetic acid benzyl ester (193156-92-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) O₃, 2.) Zn, AcOH / 1.) CH₂Cl₂, -78 deg C, 2.) 0 deg C

2: 85 percent / DIEA, NaB(OAc)3H / tetrahydrofuran; acetic acid / 0 °C

3: 80 percent / DCC, HOBt, DIEA / CH₂Cl₂

With sodium tris(acetoxy)borohydride; benzotriazol-1-ol; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; dichloromethane; acetic acid;

DOI:10.1016/S0960-894X(97)00255-2

upstream raw materials:

2-(2,3,4,6-tetra-O-acetylated-1-deoxy-α-D-galactopyranosyl)-ethanoic acid

[2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethylamino]-acetic acid benzyl ester

Gly-OBz

2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)acetaldehyde

Downstream raw materials:

C₆₄H₇₈N₄O₂₅

4-(2-{[2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-acetyl]-[2-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethyl]-amino}-acetylamino)-benzoic acid

4-(2-{[2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-acetyl]-[2-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethyl]-amino}-acetylamino)-benzoic acid benzyl ester

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