phenyl 2,3,4-tri-O-benzoyl-6-O-(t-butyldiphenylsilyl)-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 2,3,4-tri-O-benzoyl-6-O-(t-butyldiphenylsilyl)-1-thio-β-D-glucopyranoside
CAS No.:185994-24-5
Molecular Formula:C₄₉H₄₆O₈SSi
Molecular Weight:823.051
Hs Code.:

Synonyms:phenyl 2,3,4-tri-O-benzoyl-6-O-(t-butyldiphenylsilyl)-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl 2,3,4-tri-O-benzoyl-6-O-(t-butyldiphenylsilyl)-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 2,3,4-tri-O-benzoyl-6-O-(t-butyldiphenylsilyl)-1-thio-β-D-glucopyranoside

There total 8 articles about phenyl 2,3,4-tri-O-benzoyl-6-O-(t-butyldiphenylsilyl)-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: 92.0%

: 98-88-4
benzoyl chloride

: 143436-69-5
phenyl 6-O-(tert-butyldiphenylsilyl)-1-thio-β-D-glucopyranoside

: 185994-24-5
phenyl 2,3,4-tri-O-benzoyl-6-O-(t-butyldiphenylsilyl)-1-thio-β-D-glucopyranoside

Guidance literature:: With dmap; triethylamine; In tetrahydrofuran; at 50 ℃; for 15h;
DOI:10.1021/ja963482g

Reference yield:

: C₄₄H₄₄O₈SSi

: 185994-24-5
phenyl 2,3,4-tri-O-benzoyl-6-O-(t-butyldiphenylsilyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / NIS, TfOH / CH₂Cl₂ / 2 h / 25 °C

2: 72 percent / HCO₂NH₄ / 10percent Pd/C / methanol; tetrahydrofuran / 2.5 h / 25 °C

3: 1.) 4-O₂N-3-OHCH₂-C₆H₃-O-Merrifield resin, Bu₃P, DIAD, (i-Pr)2NEt, 2.) ZnI₂, Bu₄NI / 1.) THF, 25 deg C, 6 h, 2.) ClCH₂CH₂Cl, 40-45 deg C, 3 h

With N-iodo-succinimide; tributylphosphine; trifluorormethanesulfonic acid; di-isopropyl azodicarboxylate; 4-O₂N-3-OHCH₂-C₆H₃-O-Merrifield resin; ammonium formate; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; zinc(II) iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/(SICI)1521-3773(19980619)37:11<1559::AID-ANIE1559>3.0.CO;2-E

Reference yield:

: 4-Benzyloxy-benzoic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl ester

: 185994-24-5
phenyl 2,3,4-tri-O-benzoyl-6-O-(t-butyldiphenylsilyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 72 percent / HCO₂NH₄ / 10percent Pd/C / methanol; tetrahydrofuran / 2.5 h / 25 °C

2: 1.) 4-O₂N-3-OHCH₂-C₆H₃-O-Merrifield resin, Bu₃P, DIAD, (i-Pr)2NEt, 2.) ZnI₂, Bu₄NI / 1.) THF, 25 deg C, 6 h, 2.) ClCH₂CH₂Cl, 40-45 deg C, 3 h

With tributylphosphine; di-isopropyl azodicarboxylate; 4-O₂N-3-OHCH₂-C₆H₃-O-Merrifield resin; ammonium formate; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; zinc(II) iodide; palladium on activated charcoal; In tetrahydrofuran; methanol;
DOI:10.1002/(SICI)1521-3773(19980619)37:11<1559::AID-ANIE1559>3.0.CO;2-E