chloro-acetic acid 3-acetoxy-6-acetoxymethyl-2-[4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-trichloroacetimidoyloxy-tetrahydro-pyran-3-yloxy]-5-chloroacetoxy-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: chloro-acetic acid 3-acetoxy-6-acetoxymethyl-2-[4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-trichloroacetimidoyloxy-tetrahydro-pyran-3-yloxy]-5-chloroacetoxy-tetrahydro-pyran-4-yl ester
• CAS No.: 251348-06-8
• Molecular Formula: C₄₄H₄₃Cl₅N₂O₁₆
• Molecular Weight: 1033.09

Synonyms:

Chemical Property of chloro-acetic acid 3-acetoxy-6-acetoxymethyl-2-[4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-trichloroacetimidoyloxy-tetrahydro-pyran-3-yloxy]-5-chloroacetoxy-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of chloro-acetic acid 3-acetoxy-6-acetoxymethyl-2-[4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-trichloroacetimidoyloxy-tetrahydro-pyran-3-yloxy]-5-chloroacetoxy-tetrahydro-pyran-4-yl ester

There total 6 articles about chloro-acetic acid 3-acetoxy-6-acetoxymethyl-2-[4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-trichloroacetimidoyloxy-tetrahydro-pyran-3-yloxy]-5-chloroacetoxy-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:

trichloroacetonitrile (545-06-2) + Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxy-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester → chloro-acetic acid 3-acetoxy-6-acetoxymethyl-2-[4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-trichloroacetimidoyloxy-tetrahydro-pyran-3-yloxy]-5-chloroacetoxy-tetrahydro-pyran-4-yl ester (251348-06-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -20 ℃;

DOI:10.1016/S0960-894X(99)00485-0

Reference yield:

D-galactose 3,4-acetonide (70834-35-4,70834-36-5) → chloro-acetic acid 3-acetoxy-6-acetoxymethyl-2-[4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-trichloroacetimidoyloxy-tetrahydro-pyran-3-yloxy]-5-chloroacetoxy-tetrahydro-pyran-4-yl ester (251348-06-8)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine

2: aq. AcOH / 80 °C

3: pyridine

4: Cl₂CHOCH₃; ZnCl₂ / 2 h

5: 81 percent / AgOTf; collidine; 4A molecular sieves / CH₂Cl₂ / -20 °C

6: TFA / CH₂Cl₂

7: DBU / CH₂Cl₂ / -20 °C

With pyridine; 2,3,5-trimethyl-pyridine; Dichloromethyl methyl ether; 4 A molecular sieve; silver trifluoromethanesulfonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; zinc(II) chloride; In dichloromethane; 1: Acetylation / 2: Hydrolysis / 3: Acylation / 4: Chlorination / 5: glycosylation / 6: Hydrolysis / 7: trichloroacetamidation;

DOI:10.1016/S0960-894X(99)00485-0

Reference yield:

Acetic acid (3aS,4R,7R,7aS)-6-acetoxy-4-acetoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester (55639-95-7,70834-37-6) → chloro-acetic acid 3-acetoxy-6-acetoxymethyl-2-[4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-trichloroacetimidoyloxy-tetrahydro-pyran-3-yloxy]-5-chloroacetoxy-tetrahydro-pyran-4-yl ester (251348-06-8)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. AcOH / 80 °C

2: pyridine

3: Cl₂CHOCH₃; ZnCl₂ / 2 h

4: 81 percent / AgOTf; collidine; 4A molecular sieves / CH₂Cl₂ / -20 °C

5: TFA / CH₂Cl₂

6: DBU / CH₂Cl₂ / -20 °C

With pyridine; 2,3,5-trimethyl-pyridine; Dichloromethyl methyl ether; 4 A molecular sieve; silver trifluoromethanesulfonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; zinc(II) chloride; In dichloromethane; 1: Hydrolysis / 2: Acylation / 3: Chlorination / 4: glycosylation / 5: Hydrolysis / 6: trichloroacetamidation;

DOI:10.1016/S0960-894X(99)00485-0

upstream raw materials:

trichloroacetonitrile

D-galactose 3,4-acetonide

Acetic acid (3aS,4R,7R,7aS)-6-acetoxy-4-acetoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

2-(trimethylsilyl)ethyl β-D-galactopyranoside

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