(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-docosyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-docosyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 256639-65-3
• Molecular Formula: C₆₉H₉₅NO₂₁
• Molecular Weight: 1274.51

Synonyms:(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-docosyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-docosyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-docosyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 7 articles about (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-docosyloxy-tetrahydro-pyran-2-ylmethoxy)-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: 50.0%

methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate (144240-36-8) + docosyl (2,3,4-tri-O-benzoyl)-β-D-glucopyranoside (256639-62-0) → (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-docosyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (256639-65-3) + (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-docosyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (256639-64-2)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at -15 ℃; for 0.5h;

DOI:10.1002/(sici)1099-0690(199911)1999:11<3175::aid-ejoc3175>3.0.co;2-o

Reference yield:

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3) → (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-docosyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (256639-65-3)

Guidance literature:

Multi-step reaction with 6 steps

1: AgClO₄; Ag₂CO₃; 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / 20 °C

2: 100 percent / NaOMe / methanol / 0.5 h / 20 °C

3: dimethylaminopyridine; pyridine / 2 h / 65 °C

4: dimethylaminopyridine; pyridine / 4 h / 20 °C

5: p-toluenesulfonic acid / CHCl₃; methanol / 3.5 h / 20 °C

6: 31 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; trifluoromethanesulfonic acid / various solvent(s); CH₂Cl₂ / 0.5 h / -15 °C

With pyridine; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium methylate; silver perchlorate; toluene-4-sulfonic acid; silver carbonate; In methanol; dichloromethane; chloroform; 1: Substitution / 2: Deacetylation / 3: Etherification / 4: Acylation / 5: Hydrolysis / 6: Substitution;

DOI:10.1002/(sici)1099-0690(199911)1999:11<3175::aid-ejoc3175>3.0.co;2-o

Reference yield:

D-glucose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-docosyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (256639-65-3)

Guidance literature:

Multi-step reaction with 7 steps

1: HBr / acetic acid / 0.5 h / 20 °C

2: AgClO₄; Ag₂CO₃; 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / 20 °C

3: 100 percent / NaOMe / methanol / 0.5 h / 20 °C

4: dimethylaminopyridine; pyridine / 2 h / 65 °C

5: dimethylaminopyridine; pyridine / 4 h / 20 °C

6: p-toluenesulfonic acid / CHCl₃; methanol / 3.5 h / 20 °C

7: 31 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; trifluoromethanesulfonic acid / various solvent(s); CH₂Cl₂ / 0.5 h / -15 °C

With pyridine; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrogen bromide; sodium methylate; silver perchlorate; toluene-4-sulfonic acid; silver carbonate; In methanol; dichloromethane; chloroform; acetic acid; 1: Substitution / 2: Substitution / 3: Deacetylation / 4: Etherification / 5: Acylation / 6: Hydrolysis / 7: Substitution;

DOI:10.1002/(sici)1099-0690(199911)1999:11<3175::aid-ejoc3175>3.0.co;2-o

upstream raw materials:

methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate

docosyl (2,3,4-tri-O-benzoyl)-β-D-glucopyranoside

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

D-glucose pentaacetate

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