phenyl [2-(trimethylsilyl)ethyl 3,4-di-O-benzyl-2-O-benzoyl-β-D-galactopyrosyluronate]-(1->4)-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl [2-(trimethylsilyl)ethyl 3,4-di-O-benzyl-2-O-benzoyl-β-D-galactopyrosyluronate]-(1->4)-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 917568-59-3
• Molecular Formula: C₅₂H₅₁Cl₄NO₁₂SSi
• Molecular Weight: 1083.94

Synonyms:phenyl [2-(trimethylsilyl)ethyl 3,4-di-O-benzyl-2-O-benzoyl-β-D-galactopyrosyluronate]-(1->4)-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside

Chemical Property of phenyl [2-(trimethylsilyl)ethyl 3,4-di-O-benzyl-2-O-benzoyl-β-D-galactopyrosyluronate]-(1->4)-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of phenyl [2-(trimethylsilyl)ethyl 3,4-di-O-benzyl-2-O-benzoyl-β-D-galactopyrosyluronate]-(1->4)-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside

There total 11 articles about phenyl [2-(trimethylsilyl)ethyl 3,4-di-O-benzyl-2-O-benzoyl-β-D-galactopyrosyluronate]-(1->4)-2-deoxy-2-tetrachlorophthalimido-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: 75.0%

phenyl 2,6-dideoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside (917568-45-7) + 2-(trimethylsilyl)ethyl (phenyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-D-galactopyrosid) uronate S-oxide (917568-43-5) → phenyl [2-(trimethylsilyl)ethyl 3,4-di-O-benzyl-2-O-benzoyl-β-D-galactopyrosyluronate]-(1->4)-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside (917568-59-3)

Guidance literature:

2-(trimethylsilyl)ethyl (phenyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-D-galactopyrosid) uronate S-oxide; With 1,2-dimethoxy-4-(2-propenyl)benzene; In dichloromethane; at 20 ℃; for 1h;

phenyl 2,6-dideoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside; With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -78 - 0 ℃; for 1h;

DOI:10.1021/ja065907x

Reference yield:

phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (196876-49-0) → phenyl [2-(trimethylsilyl)ethyl 3,4-di-O-benzyl-2-O-benzoyl-β-D-galactopyrosyluronate]-(1->4)-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside (917568-59-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 90 percent / BH₃*THF; dibutylboron triflate / CH₂Cl₂ / 1 h / 0 °C

2.1: TEMPO; BAIB / CH₂Cl₂; H₂O / 1 h

3.1: 1.48 g / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 20 °C

4.1: 85 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 2 h / -78 - 0 °C

5.1: 4-allyl-1,2-dimethoxybenzene / CH₂Cl₂ / 1 h / 20 °C

5.2: 75 percent / triflic anhydride; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1 h / -78 - 0 °C

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; borane-THF; [bis(acetoxy)iodo]benzene; 1,2-dimethoxy-4-(2-propenyl)benzene; di-n-butylboryl trifluoromethanesulfonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water;

DOI:10.1021/ja065907x

Reference yield:

phenyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-D-galactopyranosiduronic acid (917568-41-3) → phenyl [2-(trimethylsilyl)ethyl 3,4-di-O-benzyl-2-O-benzoyl-β-D-galactopyrosyluronate]-(1->4)-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside (917568-59-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1.48 g / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 20 °C

2.1: 85 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 2 h / -78 - 0 °C

3.1: 4-allyl-1,2-dimethoxybenzene / CH₂Cl₂ / 1 h / 20 °C

3.2: 75 percent / triflic anhydride; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1 h / -78 - 0 °C

With dmap; 1,2-dimethoxy-4-(2-propenyl)benzene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/ja065907x

upstream raw materials:

phenyl 2,6-dideoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside

2-(trimethylsilyl)ethyl (phenyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-D-galactopyrosid) uronate S-oxide

phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

phenyl 2-O-benzoyl-3,4-di-O-benzyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

phenyl [2-(trimethylsilyl)ethyl 3,4-di-O-benzyl-2-O-benzoyl-β-D-galactopyrosyluronate]-(1->4)-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside S-oxide

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