N-[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetyl-N'-biotinyl-3,6-dioxaoctane-1,8-diamine

Base Information

Chemical Name:N-[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetyl-N'-biotinyl-3,6-dioxaoctane-1,8-diamine
CAS No.:476330-53-7
Molecular Formula:C₃₈H₅₃FN₄O₁₅S
Molecular Weight:856.921
Hs Code.:

Synonyms:N-[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetyl-N'-biotinyl-3,6-dioxaoctane-1,8-diamine

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Chemical Property of N-[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetyl-N'-biotinyl-3,6-dioxaoctane-1,8-diamine

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Technology Process of N-[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetyl-N'-biotinyl-3,6-dioxaoctane-1,8-diamine

There total 9 articles about N-[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetyl-N'-biotinyl-3,6-dioxaoctane-1,8-diamine 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: 83.0%

: 194920-57-5
2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethylammonium 2,2,2-trifluoroacetate

: 476330-52-6
triethylammonium [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetate

: 476330-53-7
N-[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetyl-N'-biotinyl-3,6-dioxaoctane-1,8-diamine

Guidance literature:: With TEA; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
DOI:10.1021/ol0265315

Reference yield:

: 27727-37-3
benzyl p-hydroxyphenylacetate

: 476330-53-7
N-[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetyl-N'-biotinyl-3,6-dioxaoctane-1,8-diamine

Guidance literature:: Multi-step reaction with 8 steps

1: 67 percent / AgOTf / CH₂Cl₂ / 2 h / cooling

2: 91 percent / H₂; MeOH / Pd/C / ethyl acetate / 1 h / 20 °C

3: 95 percent / DCC; DMAP / CH₂Cl₂ / 10 h / 20 °C

4: 92 percent / NBS / AlBN / CCl₄ / 1 h / Irradiation

5: 55 percent / AgNO₃; Ag₂CO₃ / acetone; H₂O / 0.5 h / 20 °C

6: 85 percent / DAST / CH₂Cl₂ / 15 h / 20 °C

7: 95 percent / DBU / CH₂Cl₂ / 0.5 h / 20 °C

8: 83 percent / TEA; HOBt; EDCl / dimethylformamide / 24 h / 20 °C

With methanol; dmap; N-Bromosuccinimide; TEA; hydrogen; silver trifluoromethanesulfonate; benzotriazol-1-ol; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; 4,4'-diaminostilbene-2,2'-disulfonic acid; silver carbonate; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol0265315

Reference yield:

: 476330-54-8
[4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acetic acid

: 476330-53-7
N-[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetyl-N'-biotinyl-3,6-dioxaoctane-1,8-diamine

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / DCC; DMAP / CH₂Cl₂ / 10 h / 20 °C

2: 92 percent / NBS / AlBN / CCl₄ / 1 h / Irradiation

3: 55 percent / AgNO₃; Ag₂CO₃ / acetone; H₂O / 0.5 h / 20 °C

4: 85 percent / DAST / CH₂Cl₂ / 15 h / 20 °C

5: 95 percent / DBU / CH₂Cl₂ / 0.5 h / 20 °C

6: 83 percent / TEA; HOBt; EDCl / dimethylformamide / 24 h / 20 °C

With dmap; N-Bromosuccinimide; TEA; benzotriazol-1-ol; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; 4,4'-diaminostilbene-2,2'-disulfonic acid; silver carbonate; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol0265315