tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:496052-69-8
Molecular Formula:C₇₈H₇₉NO₁₂Si
Molecular Weight:1250.57
Hs Code.:

Synonyms:tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Chemical Property of tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Technology Process of tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 5 articles about tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-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: 84.0%

: 100-39-0
benzyl bromide

: 496052-68-7
2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxy)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

: 496052-69-8
tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 4h;
DOI:10.1271/bbb.66.1904

Reference yield:

: tert-butyldiphenylsilyl 2-phthalimido-3,6-di-O-benzyl-2-deoxy-β-D-dlucopyranoside

: 496052-69-8
tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h

1.2: 20 percent / AgOTf / CH₂Cl₂ / 1 h / -20 °C

2.1: 83 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 0.33 h / -10 °C

3.1: 0.86 g / NaOMe / methanol / 2 h / 20 °C

4.1: 84 percent / Bu₄NI; NaH / dimethylformamide / 4 h / 0 - 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1271/bbb.66.1904

Reference yield:

: 496052-67-6
acetic acid 6-acetoxy-5-acetoxymethyl-2-[4-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-yl ester

: 496052-69-8
tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 83 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 0.33 h / -10 °C

2: 0.86 g / NaOMe / methanol / 2 h / 20 °C

3: 84 percent / Bu₄NI; NaH / dimethylformamide / 4 h / 0 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1271/bbb.66.1904