4-(N-hydroxylureidyl)butyn-1-yl 2,3-O-isopropylidene-5-O-(4-fluorophenyl)-α-D-lyxo-furanoside

Base Information

Chemical Name:4-(N-hydroxylureidyl)butyn-1-yl 2,3-O-isopropylidene-5-O-(4-fluorophenyl)-α-D-lyxo-furanoside
CAS No.:851387-24-1
Molecular Formula:C₁₉H₂₃FN₂O₆
Molecular Weight:394.4
Hs Code.:

Synonyms:4-(N-hydroxylureidyl)butyn-1-yl 2,3-O-isopropylidene-5-O-(4-fluorophenyl)-α-D-lyxo-furanoside

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Chemical Property of 4-(N-hydroxylureidyl)butyn-1-yl 2,3-O-isopropylidene-5-O-(4-fluorophenyl)-α-D-lyxo-furanoside

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Technology Process of 4-(N-hydroxylureidyl)butyn-1-yl 2,3-O-isopropylidene-5-O-(4-fluorophenyl)-α-D-lyxo-furanoside

There total 10 articles about 4-(N-hydroxylureidyl)butyn-1-yl 2,3-O-isopropylidene-5-O-(4-fluorophenyl)-α-D-lyxo-furanoside 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: 66.0%

: 851387-23-0
4-(N,O-bis(phenoxycarbonyl)hydroxylamino)butyn-1-yl 2,3-O-isopropylidene-5-O-(4-fluorophenyl)-α-D-lyxo-furanoside

: 851387-24-1
4-(N-hydroxylureidyl)butyn-1-yl 2,3-O-isopropylidene-5-O-(4-fluorophenyl)-α-D-lyxo-furanoside

Guidance literature:: With ammonium hydroxide; In methanol; at 20 ℃; for 3h;
DOI:10.1016/j.tetasy.2005.01.046

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3,5,6-di-O-isopropylidene-D-mannofuranose

: 851387-24-1
4-(N-hydroxylureidyl)butyn-1-yl 2,3-O-isopropylidene-5-O-(4-fluorophenyl)-α-D-lyxo-furanoside

Guidance literature:: Multi-step reaction with 10 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 43 percent / tetrahydrofuran; hexane / 1 h / 20 °C

2.1: 93 percent / DEAD; PPh₃ / CH₂Cl₂ / 20 °C

3.1: 70 percent / HCl / methanol / 2 h / 20 °C

4.1: NaHCO₃; NaIO₄ / CH₂Cl₂ / 5 h / 20 °C

5.1: 60 percent / NaBH₄; MeOH / 0 - 20 °C

6.1: 94 percent / Et₃N / CH₂Cl₂ / 8 h / 20 °C

7.1: 75 percent / NaH / dimethylformamide / 4 h / 80 °C

8.1: 69 percent / DDQ / CH₂Cl₂; H₂O / 5 h / 20 °C

9.1: 99 percent / DIAD; PPh₃ / CH₂Cl₂ / 1 h / 20 °C

10.1: 66 percent / NH₄OH / methanol / 3 h / 20 °C

With hydrogenchloride; methanol; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; di-isopropyl azodicarboxylate; sodium hydride; sodium hydrogencarbonate; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 2.1: Mitsunobu reaction / 9.1: Mitsunobu reaction;
DOI:10.1016/j.tetasy.2005.01.046

Reference yield:

: 851387-18-3
4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-α-D-lyxo-pentanedialdo-1,4-furanoside

: 851387-24-1
4-(N-hydroxylureidyl)butyn-1-yl 2,3-O-isopropylidene-5-O-(4-fluorophenyl)-α-D-lyxo-furanoside

Guidance literature:: Multi-step reaction with 6 steps

1: 60 percent / NaBH₄; MeOH / 0 - 20 °C

2: 94 percent / Et₃N / CH₂Cl₂ / 8 h / 20 °C

3: 75 percent / NaH / dimethylformamide / 4 h / 80 °C

4: 69 percent / DDQ / CH₂Cl₂; H₂O / 5 h / 20 °C

5: 99 percent / DIAD; PPh₃ / CH₂Cl₂ / 1 h / 20 °C

6: 66 percent / NH₄OH / methanol / 3 h / 20 °C

With methanol; ammonium hydroxide; sodium tetrahydroborate; di-isopropyl azodicarboxylate; sodium hydride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; N,N-dimethyl-formamide; 5: Mitsunobu reaction;
DOI:10.1016/j.tetasy.2005.01.046