(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid pentafluorophenyl ester

Base Information

Chemical Name:(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid pentafluorophenyl ester
CAS No.:178447-00-2
Molecular Formula:C₄₅H₄₅F₅N₄O₁₈
Molecular Weight:1024.86
Hs Code.:

(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid pentafluorophenyl ester

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Chemical Property of (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid pentafluorophenyl ester

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Technology Process of (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid pentafluorophenyl ester

There total 7 articles about (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid pentafluorophenyl ester 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:

: 182369-96-6
(2S,3R)-3-[(2S,4aR,6S,7R,8R,8aR)-7-Azido-2-phenyl-8-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid pentafluorophenyl ester

: 178447-00-2
(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid pentafluorophenyl ester

Guidance literature:: With acetic acid; at 70 ℃; for 7h;
DOI:10.1039/p19960000985

Reference yield:

: 771-61-9
2,3,4,5,6-pentafluorophenol

: 178447-00-2
(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid pentafluorophenyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 75 percent / DCC / ethyl acetate / Ambient temperature

2: 89 percent / TMSOTf, molecular sieves 3 Angstroem / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) 0 deg C to r.t., 1 h

3: 80percent aq. AcOH / 7 h / 70 °C

With trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane; ethyl acetate;
DOI:10.1039/p19960000985

Reference yield:

: 120791-77-7
N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-galactopyranosyl)-1-threonine tert-butyl ester

: 178447-00-2
(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid pentafluorophenyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / HCO₂H / 12 h / Ambient temperature

2: 65 percent / N₂H₄*H₂O / methanol / 7.5 h / Ambient temperature

3: 73 percent / p-TsOH / nitromethane / 3 h / Ambient temperature

4: 75 percent / DCC / ethyl acetate / Ambient temperature

5: 89 percent / TMSOTf, molecular sieves 3 Angstroem / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) 0 deg C to r.t., 1 h

6: 80percent aq. AcOH / 7 h / 70 °C

With formic acid; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; dicyclohexyl-carbodiimide; In methanol; nitromethane; dichloromethane; ethyl acetate;
DOI:10.1039/p19960000985