2,3,4-tri-O-benzoyl-6-O-triisopropylsilyl-α-D-glucopyranoside trichloroacetimidate

Base Information

• Chemical Name: 2,3,4-tri-O-benzoyl-6-O-triisopropylsilyl-α-D-glucopyranoside trichloroacetimidate
• CAS No.: 1300064-64-5
• Molecular Formula: C₃₈H₄₄Cl₃NO₉Si
• Molecular Weight: 793.213

Synonyms:2,3,4-tri-O-benzoyl-6-O-triisopropylsilyl-α-D-glucopyranoside trichloroacetimidate

Chemical Property of 2,3,4-tri-O-benzoyl-6-O-triisopropylsilyl-α-D-glucopyranoside trichloroacetimidate

Chemical Property:

Purity/Quality:

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Technology Process of 2,3,4-tri-O-benzoyl-6-O-triisopropylsilyl-α-D-glucopyranoside trichloroacetimidate

There total 5 articles about 2,3,4-tri-O-benzoyl-6-O-triisopropylsilyl-α-D-glucopyranoside trichloroacetimidate 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: 72.0%

phenyl 2,3,4-tri-O-benzoyl-1-thio-6-O-triisopropylsilyl-β-D-glucopyranoside (1300064-13-4) + trichloroacetonitrile (545-06-2) → 2,3,4-tri-O-benzoyl-6-O-triisopropylsilyl-α-D-glucopyranoside trichloroacetimidate (1300064-64-5)

Guidance literature:

phenyl 2,3,4-tri-O-benzoyl-1-thio-6-O-triisopropylsilyl-β-D-glucopyranoside; With N-Bromosuccinimide; In acetone; at 20 ℃; for 0.5h; Inert atmosphere;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 1h; Inert atmosphere;

DOI:10.1039/c0cc05580h

Reference yield:

C21H36O5SSi → 2,3,4-tri-O-benzoyl-6-O-triisopropylsilyl-α-D-glucopyranoside trichloroacetimidate (1300064-64-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine; dmap / Inert atmosphere

2.1: N-Bromosuccinimide / acetone / 0.5 h / 20 °C / Inert atmosphere

2.2: 1 h / Inert atmosphere

With pyridine; dmap; N-Bromosuccinimide; In acetone;

DOI:10.1039/c0cc05580h

Reference yield:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) → 2,3,4-tri-O-benzoyl-6-O-triisopropylsilyl-α-D-glucopyranoside trichloroacetimidate (1300064-64-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

2.1: pyridine; dmap / Inert atmosphere

3.1: N-Bromosuccinimide / acetone / 0.5 h / 20 °C / Inert atmosphere

3.2: 1 h / Inert atmosphere

With pyridine; 1H-imidazole; dmap; N-Bromosuccinimide; In N,N-dimethyl-formamide; acetone;

DOI:10.1039/c0cc05580h

upstream raw materials:

phenyl 2,3,4-tri-O-benzoyl-1-thio-6-O-triisopropylsilyl-β-D-glucopyranoside

trichloroacetonitrile

D-glucose pentaacetate

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

Downstream raw materials:

4--(1--methyl--3--methyleneimidazolium)--benzyl 2,3,4--tri--O-benzoyl--6--O--(2,3,4--tri--O--benzoyl--6--O--triisopropylsilyl--β--D--glucopyranosyl)--β--D--glucopyranoside trifluoromethanesulfonate

4--(1--methyl--3--methyleneimidazolium)--benzyl 2,3,4--tri--O-benzoyl--6--O--(2,3,4--tri--O--benzoyl--β--D--glucopyranosyl)--β--D--glucopyranoside trifluoromethanesulfonate

4--(1--methyl--3--methyleneimidazolium)--benzyl 2,3,4--tri--O-benzoyl--6--O--(2,3,4--tri--O--benzoyl--6--O--(2,3,4--tri--O--benzoyl--β--D--glucopyranosyl)--β--D--glucopyranosyl)--β--D--glucopyranoside trifluoromethanesulfonate

4--(1--methyl--3--methyleneimidazolium)--benzyl 2,3,4--tri--O-benzoyl--6--O--(2,3,4--tri--O--benzoyl--6--O--(2,3,4--tri--O--benzoyl--6--O--(2,3,4--tri--O--benzoyl--β--D--glucopyranosyl)--β--D--glucopyranosyl)--β--D--glucopyranosyl)--β--D--glucopyranoside trifluoromethanesulfonate

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