O-(4-O-tert-butyldimethylsilyl-2-deoxy-3-O-methyl-2-thiophenyl-6-O-tosyl-α-D-glucopyranosyl)trichloroacetimidate

Base Information

Chemical Name:O-(4-O-tert-butyldimethylsilyl-2-deoxy-3-O-methyl-2-thiophenyl-6-O-tosyl-α-D-glucopyranosyl)trichloroacetimidate
CAS No.:795289-95-1
Molecular Formula:C₂₈H₃₈Cl₃NO₇S₂Si
Molecular Weight:699.189
Hs Code.:

Synonyms:O-(4-O-tert-butyldimethylsilyl-2-deoxy-3-O-methyl-2-thiophenyl-6-O-tosyl-α-D-glucopyranosyl)trichloroacetimidate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of O-(4-O-tert-butyldimethylsilyl-2-deoxy-3-O-methyl-2-thiophenyl-6-O-tosyl-α-D-glucopyranosyl)trichloroacetimidate

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Technology Process of O-(4-O-tert-butyldimethylsilyl-2-deoxy-3-O-methyl-2-thiophenyl-6-O-tosyl-α-D-glucopyranosyl)trichloroacetimidate

There total 11 articles about O-(4-O-tert-butyldimethylsilyl-2-deoxy-3-O-methyl-2-thiophenyl-6-O-tosyl-α-D-glucopyranosyl)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: 91.0%

: 847944-57-4
Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4-methoxy-5-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

: 545-06-2
trichloroacetonitrile

: 795289-95-1
O-(4-O-tert-butyldimethylsilyl-2-deoxy-3-O-methyl-2-thiophenyl-6-O-tosyl-α-D-glucopyranosyl)trichloroacetimidate

Guidance literature:: With sodium hydride;
DOI:10.1002/anie.200460172

Reference yield:

: 795289-93-9
4,6-O-(di-tert-butyl)-silyliden-3-O-methyl-D-glucal

: 795289-95-1
O-(4-O-tert-butyldimethylsilyl-2-deoxy-3-O-methyl-2-thiophenyl-6-O-tosyl-α-D-glucopyranosyl)trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 74 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

2.1: 94 percent / pyridine / CH₂Cl₂ / 14 h / 20 °C

3.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -60 °C

4.1: NCS / CH₂Cl₂ / 1 h / 20 °C

4.2: 87 percent / Ag₂CO₃ / acetonitrile; H₂O / 14 h / 20 °C

5.1: 79 percent / NaH / various solvent(s) / 2 h / -40 - -5 °C

With pyridine; 2,6-dimethylpyridine; N-chloro-succinimide; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.200600462

Reference yield:

: 916221-16-4
Toluene-4-sulfonic acid (2R,3S,4R)-3-hydroxy-4-methoxy-3,4-dihydro-2H-pyran-2-ylmethyl ester

: 795289-95-1
O-(4-O-tert-butyldimethylsilyl-2-deoxy-3-O-methyl-2-thiophenyl-6-O-tosyl-α-D-glucopyranosyl)trichloroacetimidate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -60 °C

2.1: NCS / CH₂Cl₂ / 1 h / 20 °C

2.2: 87 percent / Ag₂CO₃ / acetonitrile; H₂O / 14 h / 20 °C

3.1: 79 percent / NaH / various solvent(s) / 2 h / -40 - -5 °C

With 2,6-dimethylpyridine; N-chloro-succinimide; sodium hydride; In dichloromethane;
DOI:10.1002/chem.200600462