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

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Chemical Name:4-(N,O-bis(phenoxycarbonyl)hydroxylamino)butyn-1-yl 2,3-O-isopropylidene-5-O-(4-fluorophenyl)-α-D-lyxo-furanoside
CAS No.:851387-23-0
Molecular Formula:C₃₂H₃₀FNO₉
Molecular Weight:591.59
Hs Code.:

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

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

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

There total 9 articles about 4-(N,O-bis(phenoxycarbonyl)hydroxylamino)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: 99.0%

: 141580-65-6
N,O-Bis(phenoxycarbonyl)hydroxylamine

: 851387-22-9
4-hydroxybutyn-1-yl 2,3-O-isopropylidene-5-O-(4-fluorophenyl)-α-D-lyxo-furanoside

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

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at 20 ℃; for 1h;
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

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

Guidance literature:: Multi-step reaction with 9 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

With hydrogenchloride; methanol; 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

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

Guidance literature:: Multi-step reaction with 5 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

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