2,5-anhydro-1,6-dideoxy-3,4-O-isopropylidene-1-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-D-talitol

Base Information

Chemical Name:2,5-anhydro-1,6-dideoxy-3,4-O-isopropylidene-1-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-D-talitol
CAS No.:1393601-99-4
Molecular Formula:C₁₆H₂₀N₄O₃S
Molecular Weight:348.426
Hs Code.:

Synonyms:2,5-anhydro-1,6-dideoxy-3,4-O-isopropylidene-1-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-D-talitol

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Chemical Property of 2,5-anhydro-1,6-dideoxy-3,4-O-isopropylidene-1-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-D-talitol

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Technology Process of 2,5-anhydro-1,6-dideoxy-3,4-O-isopropylidene-1-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-D-talitol

There total 4 articles about 2,5-anhydro-1,6-dideoxy-3,4-O-isopropylidene-1-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-D-talitol 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: 94.0%

: 76222-68-9
((3aR,4R,6R,6aS)-2,2,6-trimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

: 86-93-1
1-Phenyl-1H-tetrazole-5-thiol

: 1393601-99-4
2,5-anhydro-1,6-dideoxy-3,4-O-isopropylidene-1-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-D-talitol

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.3998/ark.5550190.0013.633

Reference yield:

: 75467-36-6
5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribonolactone

: 1393601-99-4
2,5-anhydro-1,6-dideoxy-3,4-O-isopropylidene-1-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-D-talitol

Guidance literature:: Multi-step reaction with 5 steps

1: diisobutylaluminium hydride / hexane; toluene / 4 h / -78 - -50 °C / Inert atmosphere

2: dmap / dichloromethane / 12 h / 0 - 20 °C

3: hexane; dichloromethane / 144 h / -30 - -18 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C

5: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h / 0 °C

With dmap; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; toluene; 5: Mitsunobu reaction;
DOI:10.3998/ark.5550190.0013.633

Reference yield:

: 30725-00-9
2,3-O-isopropylidene-D-ribonic-γ-lactone

: 1393601-99-4
2,5-anhydro-1,6-dideoxy-3,4-O-isopropylidene-1-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-D-talitol

Guidance literature:: Multi-step reaction with 6 steps

1: dmap; triethylamine / N,N-dimethyl-formamide / 8 h / 20 °C

2: diisobutylaluminium hydride / hexane; toluene / 4 h / -78 - -50 °C / Inert atmosphere

3: dmap / dichloromethane / 12 h / 0 - 20 °C

4: hexane; dichloromethane / 144 h / -30 - -18 °C

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C

6: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h / 0 °C

With dmap; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 6: Mitsunobu reaction;
DOI:10.3998/ark.5550190.0013.633