phenyl 6-O-benzyl-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 6-O-benzyl-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside
• CAS No.: 1352630-95-5
• Molecular Formula: C₅₅H₅₀N₂O₁₂S
• Molecular Weight: 963.074

Synonyms:phenyl 6-O-benzyl-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 6-O-benzyl-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of phenyl 6-O-benzyl-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside

There total 4 articles about phenyl 6-O-benzyl-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-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:

phenyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside S-oxide (1352630-94-4) → phenyl 6-O-benzyl-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside (1352630-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,6-di-tert-butyl-4-methylpyridine; 1,2-dimethoxy-4-(2-propenyl)benzene / dichloromethane / 0.75 h / 20 °C / Inert atmosphere; Molecular sieve

1.2: 4 h / -78 - -40 °C / Inert atmosphere; Molecular sieve

2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

With triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; 1,2-dimethoxy-4-(2-propenyl)benzene; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/j.tet.2011.09.114

Reference yield:

benzyl bromide (100-39-0) → phenyl 6-O-benzyl-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside (1352630-95-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C / Inert atmosphere

1.2: 20 h / 20 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.75 h / -78 - 20 °C / Inert atmosphere

3.1: 2,6-di-tert-butyl-4-methylpyridine; 1,2-dimethoxy-4-(2-propenyl)benzene / dichloromethane / 0.75 h / 20 °C / Inert atmosphere; Molecular sieve

3.2: 4 h / -78 - -40 °C / Inert atmosphere; Molecular sieve

4.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C / Inert atmosphere

4.2: 0 °C / Inert atmosphere

With triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; 1,2-dimethoxy-4-(2-propenyl)benzene; boron trifluoride diethyl etherate; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.tet.2011.09.114

Reference yield:

phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-1-deoxy-β-D-glucopyranoside (141342-83-8) → phenyl 6-O-benzyl-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside (1352630-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,6-di-tert-butyl-4-methylpyridine; 1,2-dimethoxy-4-(2-propenyl)benzene / dichloromethane / 0.75 h / 20 °C / Inert atmosphere; Molecular sieve

1.2: 4 h / -78 - -40 °C / Inert atmosphere; Molecular sieve

2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

With triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; 1,2-dimethoxy-4-(2-propenyl)benzene; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/j.tet.2011.09.114

upstream raw materials:

phenyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside S-oxide

benzyl bromide

phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-1-deoxy-β-D-glucopyranoside

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

Downstream raw materials:

C₁₀₄H₉₂N₄O₂₄S

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