4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

Base Information

Chemical Name:4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose
CAS No.:205750-48-7
Molecular Formula:C₃₃H₃₄N₄O₁₃
Molecular Weight:694.652
Hs Code.:

Synonyms:4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

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Chemical Property of 4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

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Technology Process of 4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

There total 1 articles about 4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 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: 96.0%

: 55682-57-0
1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

: 79528-49-7
phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 205750-48-7
4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

Guidance literature:: With N-iodo-succinimide; molecular sieve; trifluoromethanesulfinic acid; In dichloromethane; for 0.5h; Ambient temperature;
DOI:10.1080/07328309808002324

Reference yield: 92.0%

: 205750-48-7
4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

: 205750-54-5
Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((1R,2S,3R,4R,5R)-4-amino-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Guidance literature:: With pyridine; hydrogen sulfide; triethylamine; Ambient temperature;
DOI:10.1080/07328309808002324

Reference yield:

: 205750-48-7
4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

: Tetradecanoic acid {(2R,3R,4R,5S,6R)-4-benzyloxy-5-[(2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-6-hydroxymethyl-2-tetradecyloxy-tetrahydro-pyran-3-yl}-amide

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / H₂S, Py/Et₃N / Ambient temperature

2: 96 percent / pyridine / 0.5 h / Ambient temperature

3: 1.) triethylsilyl triflate, 2.) (+)-10-camphorsulfonic acid / 1.) room temperature, 30 min, 2.) 1,2-dichloroethane, 90 deg C, 30 min

4: trimethylsilyl triflate / 1,2-dichloro-ethane / 1 h / 50 °C

5: (+)-10-camphorsulfonic acid / 1,2-dichloro-ethane / 0.5 h / 90 °C

6: NaOMe / methanol / 4.5 h / Ambient temperature

With pyridine; trimethylsilyl trifluoromethanesulfonate; hydrogen sulfide; triethylsilyl trifluoromethyl sulfonate; sodium methylate; (+)-10-camphorsulfonic acid; triethylamine; In pyridine; methanol; 1,2-dichloro-ethane;
DOI:10.1080/07328309808002324