(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{2,4-dimethoxy-5-[4-methoxy-3-((2R,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yl)-benzyl]-phenyl}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{2,4-dimethoxy-5-[4-methoxy-3-((2R,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yl)-benzyl]-phenyl}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 263148-81-8
• Molecular Formula: C₄₈H₆₁NO₂₂
• Molecular Weight: 1004.01

Synonyms:(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{2,4-dimethoxy-5-[4-methoxy-3-((2R,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yl)-benzyl]-phenyl}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{2,4-dimethoxy-5-[4-methoxy-3-((2R,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yl)-benzyl]-phenyl}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{2,4-dimethoxy-5-[4-methoxy-3-((2R,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yl)-benzyl]-phenyl}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 4 articles about (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{2,4-dimethoxy-5-[4-methoxy-3-((2R,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yl)-benzyl]-phenyl}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl 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: 76.0%

Acetic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-2-(5-bromomethyl-2-methoxy-phenyl)-6-methyl-tetrahydro-pyran-3-yl ester (263148-79-4) + (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(2,4-dimethoxy-5-tributylstannanyl-phenyl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester → (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{2,4-dimethoxy-5-[4-methoxy-3-((2R,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yl)-benzyl]-phenyl}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (263148-81-8)

Guidance literature:

With potassium carbonate; Triphenylphosphine oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; Heating;

DOI:10.1055/s-1999-2738

Reference yield:

p-methylanizole (104-93-8) → (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{2,4-dimethoxy-5-[4-methoxy-3-((2R,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yl)-benzyl]-phenyl}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (263148-81-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / SnCl₄, silver trifluoroacetate / CH₂Cl₂

2: 65 percent / NBS, AIBN / CCl₄

3: 76 percent / K₂CO₃, Ph₃P=O / Pd(PPh₃)4 / dioxane / Heating

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); silver trifluoroacetate; tin(IV) chloride; potassium carbonate; Triphenylphosphine oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; tetrachloromethane; dichloromethane;

DOI:10.1055/s-1999-2738

Reference yield:

4-methoxy-3-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)toluene (189135-52-2) → (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{2,4-dimethoxy-5-[4-methoxy-3-((2R,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yl)-benzyl]-phenyl}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (263148-81-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / NBS, AIBN / CCl₄

2: 76 percent / K₂CO₃, Ph₃P=O / Pd(PPh₃)4 / dioxane / Heating

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); potassium carbonate; Triphenylphosphine oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; tetrachloromethane;

DOI:10.1055/s-1999-2738

upstream raw materials:

Acetic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-2-(5-bromomethyl-2-methoxy-phenyl)-6-methyl-tetrahydro-pyran-3-yl ester

p-methylanizole

4-methoxy-3-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)toluene

1,2,3,4-tetra-O-acetyl-β-L-fucopyranose

Downstream raw materials:

(2S,4S,5R,6R)-5-Acetylamino-2-{2,4-dimethoxy-5-[4-methoxy-3-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yl)-benzyl]-phenyl}-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

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