6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose

Base Information

• Chemical Name: 6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose
• CAS No.: 108788-52-9
• Molecular Formula: C₁₇H₂₃N₃O₆
• Molecular Weight: 365.386

Synonyms:6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose

Chemical Property of 6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose

Chemical Property:

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Technology Process of 6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose

There total 11 articles about 6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose 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: 92.0%

5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose (108788-44-9) → 6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose (108788-52-9)

Guidance literature:

With sodium azide; Trimethyl borate; In N,N-dimethyl-formamide; at 70 ℃; for 48h; regioselective reaction;

DOI:10.1016/j.tetasy.2012.12.005

Reference yield: 80.9%

3-O-benzyl-5,6-anhydro-1,2-O-isopropylidene-β-L-glycero-D-gluco-hepto-1,4-furanose (108788-46-1) → 5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-glycero-L-ido-hepto-1,4-furanose (1224467-47-3) + 6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose (108788-52-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; for 6h; Reflux; Inert atmosphere;

DOI:10.1016/j.tetasy.2010.01.007

Reference yield: 73.0%

3-O-benzyl-5,6-anhydro-1,2-O-isopropylidene-β-L-glycero-D-gluco-hepto-1,4-furanose (108788-46-1) → 6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose (108788-52-9)

Guidance literature:

With sodium azide; ammonium chloride; In 2-methoxy-ethanol; water; at 125 ℃; for 2h;

DOI:10.1248/cpb.34.3102

upstream raw materials:

3-O-benzyl-5,6-anhydro-1,2-O-isopropylidene-β-L-glycero-D-gluco-hepto-1,4-furanose

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

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

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

Downstream raw materials:

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

5,7-anhydro-6-N-benzyloxycarbonylamino-6-deoxy-D-glycero-D-gluco-heptitol

5,7-anhydro-6-N-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

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

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