1,4-anhydro-5-deoxy-2,3-O-isopropylidene-1-methyl-5-(1-phenyl-1H-tetrazol-5-ylsulfonyl)-D-galacto-pentitol

Base Information

• Chemical Name: 1,4-anhydro-5-deoxy-2,3-O-isopropylidene-1-methyl-5-(1-phenyl-1H-tetrazol-5-ylsulfonyl)-D-galacto-pentitol
• CAS No.: 1260096-98-7
• Molecular Formula: C₁₆H₂₀N₄O₅S
• Molecular Weight: 380.425

Synonyms:1,4-anhydro-5-deoxy-2,3-O-isopropylidene-1-methyl-5-(1-phenyl-1H-tetrazol-5-ylsulfonyl)-D-galacto-pentitol

Chemical Property of 1,4-anhydro-5-deoxy-2,3-O-isopropylidene-1-methyl-5-(1-phenyl-1H-tetrazol-5-ylsulfonyl)-D-galacto-pentitol

Chemical Property:

Purity/Quality:

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Technology Process of 1,4-anhydro-5-deoxy-2,3-O-isopropylidene-1-methyl-5-(1-phenyl-1H-tetrazol-5-ylsulfonyl)-D-galacto-pentitol

There total 6 articles about 1,4-anhydro-5-deoxy-2,3-O-isopropylidene-1-methyl-5-(1-phenyl-1H-tetrazol-5-ylsulfonyl)-D-galacto-pentitol 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: 91.0%

1,4-anhydro-5-deoxy-2,3-O-isopropylidene-1-methyl-5-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-D-galacto-pentitol (1260097-00-4) → 1,4-anhydro-5-deoxy-2,3-O-isopropylidene-1-methyl-5-(1-phenyl-1H-tetrazol-5-ylsulfonyl)-D-galacto-pentitol (1260096-98-7)

Guidance literature:

With ammonium molibdate; dihydrogen peroxide; In tetrahydrofuran; ethanol; water; at 0 - 20 ℃; for 48h;

DOI:10.1055/s-0030-1258201

Reference yield:

2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9) → 1,4-anhydro-5-deoxy-2,3-O-isopropylidene-1-methyl-5-(1-phenyl-1H-tetrazol-5-ylsulfonyl)-D-galacto-pentitol (1260096-98-7)

Guidance literature:

Multi-step reaction with 7 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

7: ammonium molybdate; dihydrogen peroxide / tetrahydrofuran; ethanol / 24 h / 20 °C

With dmap; ammonium molybdate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 6: Mitsunobu reaction;

DOI:10.3998/ark.5550190.0013.633

Reference yield:

5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribonolactone (75467-36-6) → 1,4-anhydro-5-deoxy-2,3-O-isopropylidene-1-methyl-5-(1-phenyl-1H-tetrazol-5-ylsulfonyl)-D-galacto-pentitol (1260096-98-7)

Guidance literature:

Multi-step reaction with 6 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

6: ammonium molybdate; dihydrogen peroxide / tetrahydrofuran; ethanol / 24 h / 20 °C

With dmap; ammonium molybdate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; 5: Mitsunobu reaction;

DOI:10.3998/ark.5550190.0013.633

upstream raw materials:

1,4-anhydro-5-deoxy-2,3-O-isopropylidene-1-methyl-5-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-D-galacto-pentitol

2,3-O-isopropylidene-D-ribonic-γ-lactone

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

1-Phenyl-1H-tetrazole-5-thiol

Downstream raw materials:

C₂₀H₂₆O₆

(2R,3S,4R,5S,E)-2-(2-(hydroxymethyl)-3-methoxystyryl)-5-methyl-tetrahydrofuran-3,4-diol

Z-varitriol

E-(2S,3R,4S,5R)-5-(2-methoxystyryl)-2-methyltetrahydrofuran-3,4-diol

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