methyl 3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 1385090-65-2
• Molecular Formula: C₄₉H₄₉NO₁₂
• Molecular Weight: 843.928

Synonyms:methyl 3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of methyl 3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of methyl 3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 7 articles about methyl 3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 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: 97.0%

methyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (1385090-63-0) → methyl 3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (1385090-65-2)

Guidance literature:

methyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside; With sodium methylate; In methanol; dichloromethane; at 20 ℃; for 0.25h; pH=10;

In methanol; dichloromethane; pH=6;

DOI:10.1021/jo300764k

Reference yield:

p-chlorophenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (1385090-31-2) → methyl 3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (1385090-65-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 3.5 h / 0 °C

2.1: dichloromethane / 2 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 16 h / -72 - 20 °C / pH 3 / Molecular sieve; Inert atmosphere

3.1: dichloromethane / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere

3.2: 16 h / -75 - 20 °C / Molecular sieve; Inert atmosphere

4.1: sodium methylate / methanol; dichloromethane / 0.25 h / 20 °C / pH 10

4.2: Amberlite IR-120H / pH 6

5.1: pyridine / dichloromethane / 16 h / 45 °C

6.1: potassium tert-butylate / 1,4-dioxane / 144 h

6.2: 16 h / 70 °C

7.1: sodium methylate / methanol; dichloromethane / 0.25 h / 20 °C / pH 10

7.2: Amberlite IR-12OH / pH 6

With pyridine; triethylsilane; boron trifluoride diethyl etherate; potassium tert-butylate; sodium methylate; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/jo300764k

Reference yield:

p-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (1385090-38-9) → methyl 3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (1385090-65-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dichloromethane / 2 h / 20 °C / Molecular sieve; Inert atmosphere

1.2: 16 h / -72 - 20 °C / pH 3 / Molecular sieve; Inert atmosphere

2.1: dichloromethane / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 16 h / -75 - 20 °C / Molecular sieve; Inert atmosphere

3.1: sodium methylate / methanol; dichloromethane / 0.25 h / 20 °C / pH 10

3.2: Amberlite IR-120H / pH 6

4.1: pyridine / dichloromethane / 16 h / 45 °C

5.1: potassium tert-butylate / 1,4-dioxane / 144 h

5.2: 16 h / 70 °C

6.1: sodium methylate / methanol; dichloromethane / 0.25 h / 20 °C / pH 10

6.2: Amberlite IR-12OH / pH 6

With pyridine; potassium tert-butylate; sodium methylate; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/jo300764k

upstream raw materials:

p-chlorophenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

p-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

p-chlorophenyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

methyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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