chloro-acetic acid 3-acetoxy-6-acetoxymethyl-2-[4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2-trimethylsilanyl-ethoxy)-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-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-5-chloroacetoxy-tetrahydro-pyran-4-yl ester
• CAS No.: 251348-04-6
• Molecular Formula: C₄₇H₅₅Cl₂NO₁₆Si
• Molecular Weight: 988.942

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

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-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-5-chloroacetoxy-tetrahydro-pyran-4-yl ester

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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-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-5-chloroacetoxy-tetrahydro-pyran-4-yl ester

There total 5 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-(2-trimethylsilanyl-ethoxy)-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: 81.0%

2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (117253-02-8) + 2,6-di-O-acetyl-3,4-di-O-chloroacetyl-α-D-galactopyranosyl chloride (251348-05-7) → chloro-acetic acid 3-acetoxy-6-acetoxymethyl-2-[4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-5-chloroacetoxy-tetrahydro-pyran-4-yl ester (251348-04-6)

Guidance literature:

With 2,3,5-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; 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-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-5-chloroacetoxy-tetrahydro-pyran-4-yl ester (251348-04-6)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; 2,3,5-trimethyl-pyridine; Dichloromethyl methyl ether; 4 A molecular sieve; silver trifluoromethanesulfonate; acetic acid; zinc(II) chloride; In dichloromethane; 1: Acetylation / 2: Hydrolysis / 3: Acylation / 4: Chlorination / 5: glycosylation;

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-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-5-chloroacetoxy-tetrahydro-pyran-4-yl ester (251348-04-6)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. AcOH / 80 °C

2: pyridine

3: Cl₂CHOCH₃; ZnCl₂ / 2 h

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

With pyridine; 2,3,5-trimethyl-pyridine; Dichloromethyl methyl ether; 4 A molecular sieve; silver trifluoromethanesulfonate; acetic acid; zinc(II) chloride; In dichloromethane; 1: Hydrolysis / 2: Acylation / 3: Chlorination / 4: glycosylation;

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

upstream raw materials:

2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

2,6-di-O-acetyl-3,4-di-O-chloroacetyl-α-D-galactopyranosyl chloride

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

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