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

Base Information

• Chemical Name: p-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 1385090-38-9
• Molecular Formula: C₃₄H₃₀ClNO₆S
• Molecular Weight: 616.134

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

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

Chemical Property:

Purity/Quality:

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

There total 3 articles about p-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-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: 86.0%

p-chlorophenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (1385090-31-2) → p-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (1385090-38-9)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 3.5h;

DOI:10.1021/jo300764k

Reference yield:

4-chlorophenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (296768-93-9) → p-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (1385090-38-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h

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

With triethylsilane; boron trifluoride diethyl etherate; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jo300764k

Reference yield:

benzyl bromide (100-39-0) → p-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (1385090-38-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h

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

With triethylsilane; boron trifluoride diethyl etherate; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

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

benzyl bromide

4-chlorophenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

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

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

C₅₀H₅₀ClNO₁₂S

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

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