5-O-(2,4-di-O-acetyl-3-O-(3-fluoropropyl)-6-deoxy-β-D-glucopyranosyl)-6,3',4'-tri-O-benzyl-1,3,2',6'-tetraazidoneamine

Base Information

Chemical Name:5-O-(2,4-di-O-acetyl-3-O-(3-fluoropropyl)-6-deoxy-β-D-glucopyranosyl)-6,3',4'-tri-O-benzyl-1,3,2',6'-tetraazidoneamine
CAS No.:675616-58-7
Molecular Formula:C₄₆H₅₅FN₁₂O₁₂
Molecular Weight:987.014
Hs Code.:

Synonyms:5-O-(2,4-di-O-acetyl-3-O-(3-fluoropropyl)-6-deoxy-β-D-glucopyranosyl)-6,3',4'-tri-O-benzyl-1,3,2',6'-tetraazidoneamine

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Chemical Property of 5-O-(2,4-di-O-acetyl-3-O-(3-fluoropropyl)-6-deoxy-β-D-glucopyranosyl)-6,3',4'-tri-O-benzyl-1,3,2',6'-tetraazidoneamine

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Technology Process of 5-O-(2,4-di-O-acetyl-3-O-(3-fluoropropyl)-6-deoxy-β-D-glucopyranosyl)-6,3',4'-tri-O-benzyl-1,3,2',6'-tetraazidoneamine

There total 6 articles about 5-O-(2,4-di-O-acetyl-3-O-(3-fluoropropyl)-6-deoxy-β-D-glucopyranosyl)-6,3',4'-tri-O-benzyl-1,3,2',6'-tetraazidoneamine 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: 68.0%

: 675616-56-5
5-O-(2,4-di-O-acetyl-3-O-(3-hydroxypropyl)-6-deoxy-β-D-glucopyranosyl)-6,3',4'-tri-O-benzyl-1,3,2',6'-tetraazidoneamine

: 675616-58-7
5-O-(2,4-di-O-acetyl-3-O-(3-fluoropropyl)-6-deoxy-β-D-glucopyranosyl)-6,3',4'-tri-O-benzyl-1,3,2',6'-tetraazidoneamine

Guidance literature:: With 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; at -30 - -10 ℃; for 3h;
DOI:10.1021/jo035290r

Reference yield:

: 134311-53-8
3-O-allyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

: 675616-58-7
5-O-(2,4-di-O-acetyl-3-O-(3-fluoropropyl)-6-deoxy-β-D-glucopyranosyl)-6,3',4'-tri-O-benzyl-1,3,2',6'-tetraazidoneamine

Guidance literature:: Multi-step reaction with 6 steps

1.1: TFA; AcOH / H₂O / 1 h / 70 °C

1.2: 96 percent / H₂SO₄ / 0 °C

2.1: hydrazine acetate / dimethylformamide / 20 °C

3.1: DBU / CH₂Cl₂ / 20 °C

4.1: 62 percent / BF₃*OEt₂ / CH₂Cl₂ / -50 °C

5.1: NH₃ / tetrahydrofuran / 3 h / 20 °C

5.2: 69 percent / NaOH; H₂O₂ / tetrahydrofuran; H₂O

6.1: 68 percent / DAST / CH₂Cl₂ / 3 h / -30 - -10 °C

With boron trifluoride diethyl etherate; ammonia; hydrazinium monoacetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-diaminostilbene-2,2'-disulfonic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo035290r

Reference yield:

: Acetic acid (3R,4S,5R,6R)-5-acetoxy-4-allyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

: 675616-58-7
5-O-(2,4-di-O-acetyl-3-O-(3-fluoropropyl)-6-deoxy-β-D-glucopyranosyl)-6,3',4'-tri-O-benzyl-1,3,2',6'-tetraazidoneamine

Guidance literature:: Multi-step reaction with 4 steps

1.1: DBU / CH₂Cl₂ / 20 °C

2.1: 62 percent / BF₃*OEt₂ / CH₂Cl₂ / -50 °C

3.1: NH₃ / tetrahydrofuran / 3 h / 20 °C

3.2: 69 percent / NaOH; H₂O₂ / tetrahydrofuran; H₂O

4.1: 68 percent / DAST / CH₂Cl₂ / 3 h / -30 - -10 °C

With boron trifluoride diethyl etherate; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo035290r