6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-α-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone

Base Information

Chemical Name:6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-α-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone
CAS No.:1352442-71-7
Molecular Formula:C₅₀H₅₆O₁₅Si
Molecular Weight:925.071
Hs Code.:

Synonyms:6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-α-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone

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Chemical Property of 6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-α-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone

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Technology Process of 6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-α-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone

There total 6 articles about 6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-α-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone 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:

: p-tolyl 6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-1-thio-β-D-galactofuranoside

: 2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone

: 1352442-72-8
6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone

: 1352442-71-7
6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-α-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone

Guidance literature:: p-tolyl 6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-1-thio-β-D-galactofuranoside; 2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone; With silver trifluoromethanesulfonate; In dichloromethane; at 20 ℃; Molecular sieve;

With 4-nitrobenzenesulfenyl chloride; In dichloromethane; at -78 ℃; for 1h; Overall yield = 65 %; Overall yield = 24 mg; Molecular sieve;
DOI:10.1016/j.carres.2014.07.024

Reference yield:

: O-(6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-D-galactofuranosyl)trichloroacetimidate

: 123765-15-1
2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone

: 1352442-72-8
6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone

: 1352442-71-7
6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-α-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at -78 ℃; for 0.666667h; diastereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1016/j.carres.2011.10.004

Reference yield:

: p-tolyl 2,6-di-O-benzoyl-3,5-O-(di-tert-butylsilanediyl)-1-thio-β-D-galactofuranoside

: 1352442-72-8
6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone

: 1352442-71-7
6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-α-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium methylate / methanol / 6 h / 0 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 0.3 h

3.1: pyridine / 2.5 h / 0 °C

4.1: silver trifluoromethanesulfonate / dichloromethane / 20 °C / Molecular sieve

4.2: 1 h / -78 °C / Molecular sieve

With pyridine; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2014.07.024