5,7-anhydro-6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

Base Information

Chemical Name:5,7-anhydro-6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose
CAS No.:108788-60-9
Molecular Formula:C₁₇H₂₁N₃O₅
Molecular Weight:347.371
Hs Code.:

Synonyms:5,7-anhydro-6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

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Chemical Property of 5,7-anhydro-6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

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Technology Process of 5,7-anhydro-6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

There total 6 articles about 5,7-anhydro-6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose 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: 75.0%

: 108788-56-3
6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-7-O-p-toluenesulfonyl-α-D-glycero-D-gluco-heptofuranose

: 108788-60-9
5,7-anhydro-6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; benzene; at 0 ℃; for 0.333333h;
DOI:10.1248/cpb.34.3102

Reference yield:

: 23558-05-6
3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

: 108788-60-9
5,7-anhydro-6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

Guidance literature:: Multi-step reaction with 6 steps

1: 43 percent / benzene / 38 h / Ambient temperature

2: 66 percent / diisobutylaluminium hydride / hexane; toluene / 3 h / Ambient temperature

3: 27 percent / m-chloroperbezoic acid / CH₂Cl₂ / 16 h / Ambient temperature

4: 73 percent / sodium azide; ammonium chloride / H₂O; 2-methoxy-ethanol / 2 h / 125 °C

5: 86 percent / pyridine / 10 h

6: 75 percent / potassium tert-butoxide / benzene; tetrahydrofuran / 0.33 h / 0 °C

With pyridine; sodium azide; ammonium chloride; potassium tert-butylate; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; 2-methoxy-ethanol; water; toluene; benzene;
DOI:10.1248/cpb.34.3102

Reference yield:

: 108182-63-4
(E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose

: 108788-60-9
5,7-anhydro-6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

Guidance literature:: Multi-step reaction with 4 steps

1: 27 percent / m-chloroperbezoic acid / CH₂Cl₂ / 16 h / Ambient temperature

2: 73 percent / sodium azide; ammonium chloride / H₂O; 2-methoxy-ethanol / 2 h / 125 °C

3: 86 percent / pyridine / 10 h

4: 75 percent / potassium tert-butoxide / benzene; tetrahydrofuran / 0.33 h / 0 °C

With pyridine; sodium azide; ammonium chloride; potassium tert-butylate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 2-methoxy-ethanol; water; benzene;
DOI:10.1248/cpb.34.3102