phenyl (2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-pivaloyl-3-O-acetyl-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl (2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-pivaloyl-3-O-acetyl-2-phthalimido-1-thio-β-D-glucopyranoside
CAS No.:635301-79-0
Molecular Formula:C₃₉H₄₄FNO₁₅S
Molecular Weight:817.84
Hs Code.:

Synonyms:phenyl (2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-pivaloyl-3-O-acetyl-2-phthalimido-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl (2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-pivaloyl-3-O-acetyl-2-phthalimido-1-thio-β-D-glucopyranoside

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Technology Process of phenyl (2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-pivaloyl-3-O-acetyl-2-phthalimido-1-thio-β-D-glucopyranoside

There total 5 articles about phenyl (2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-pivaloyl-3-O-acetyl-2-phthalimido-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: 63.0%

: 108-24-7
acetic anhydride

: 686343-23-7
2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6S)-3-((2R,3R,4R,5S,6R)-3,4-diacetoxy-6-acetoxymethyl-5-fluoro-tetrahydro-pyran-2-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

: 635301-79-0
phenyl (2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-pivaloyl-3-O-acetyl-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: With pyridine; dmap; at 20 ℃; for 12h;
DOI:10.1055/s-2003-40342

Reference yield:

: 183506-73-2
4-deoxy-4-fluoro-1,2,3,6-tetra-O-acetyl-D-galactopyranose

: 635301-79-0
phenyl (2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-pivaloyl-3-O-acetyl-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: hydrazine acetic acid / dimethylformamide / 2 h / 50 °C

2: DBU / CH₂Cl₂ / 2 h / 0 - 25 °C

3: 41 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 2.5 h / -70 - -65 °C

4: 63 percent / pyridine; DMAP / 20 °C

With pyridine; dmap; hydrazineacetic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo052626j

Reference yield:

: 183293-21-2
2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-α-D-galactopyranosyl trichloroacetimidate

: 635301-79-0
phenyl (2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-pivaloyl-3-O-acetyl-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 41 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 2.5 h / -70 - -65 °C

2: 63 percent / pyridine; DMAP / 20 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane;
DOI:10.1021/jo052626j