phenyl 4,6-O-benzylidene-3-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 4,6-O-benzylidene-3-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
CAS No.:1621188-57-5
Molecular Formula:C₄₉H₇₈Cl₃NO₁₁SSi₃
Molecular Weight:1079.84
Hs Code.:

phenyl 4,6-O-benzylidene-3-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Synonyms:phenyl 4,6-O-benzylidene-3-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

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Chemical Property of phenyl 4,6-O-benzylidene-3-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

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Technology Process of phenyl 4,6-O-benzylidene-3-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

There total 8 articles about phenyl 4,6-O-benzylidene-3-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-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: 81.0%

: 1621188-32-6
1,2-dideoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose

: phenyl N-(2,2,2-trichloroethoxy)carbonyl-2-amino-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

: 1621188-57-5
phenyl 4,6-O-benzylidene-3-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; water; at 20 ℃; for 4h; stereoselective reaction; Inert atmosphere;
DOI:10.1002/anie.201403543

Reference yield:

: 13265-84-4
D-glucal

: 1621188-57-5
phenyl 4,6-O-benzylidene-3-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere

2: pyridine / N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere

3: toluene-4-sulfonic acid / dichloromethane; water / 4 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; toluene-4-sulfonic acid; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/anie.201403543

Reference yield:

: 108-98-5
thiophenol

: 1621188-57-5
phenyl 4,6-O-benzylidene-3-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: boron trifluoride diethyl etherate / dichloromethane / 18 h / 20 °C

2: water; methanol; triethylamine / 18 h

3: copper(II) bis(trifluoromethanesulfonate) / acetonitrile / 2 h / 20 °C / Inert atmosphere

4: toluene-4-sulfonic acid / dichloromethane; water / 4 h / 20 °C / Inert atmosphere

With methanol; boron trifluoride diethyl etherate; water; copper(II) bis(trifluoromethanesulfonate); toluene-4-sulfonic acid; triethylamine; In dichloromethane; water; acetonitrile;
DOI:10.1002/anie.201403543