(Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-ribofuranos-5-ylidene)amine N-oxide

Base Information

• Chemical Name: (Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-ribofuranos-5-ylidene)amine N-oxide
• CAS No.: 191721-03-6
• Molecular Formula: C₂₂H₂₅NO₅
• Molecular Weight: 383.444

Synonyms:(Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-ribofuranos-5-ylidene)amine N-oxide

Chemical Property of (Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-ribofuranos-5-ylidene)amine N-oxide

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Technology Process of (Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-ribofuranos-5-ylidene)amine N-oxide

There total 1 articles about (Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-ribofuranos-5-ylidene)amine N-oxide 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: 74.0%

3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose (63593-02-2) + N-benzylhydroxylamine hydrochloride (29601-98-7) → (Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-ribofuranos-5-ylidene)amine N-oxide (191721-03-6)

Guidance literature:

With sodium acetate; In ethanol; water; for 0.583333h; Ambient temperature;

DOI:10.1016/S0957-4166(97)00147-X

Reference yield: 40.0%

(Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-ribofuranos-5-ylidene)amine N-oxide (191721-03-6) + ethenyltrimethylsilane (754-05-2) → (3R,5S)-2-benzyl-3-(3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-tetrofuranos-4-yl)-5-(trimethylsilyl)isoxazolidine + (3R,5R)-2-benzyl-3-(3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-tetrofuranos-4-yl)-5-(trimethylsilyl)isoxazolidine + (3S)-2-benzyl-3-(3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-tetrofuranos-4-yl)-5-(trimethylsilyl)isoxazolidine

Guidance literature:

In toluene; at 80 ℃; for 20h;

DOI:10.1016/S0957-4166(02)00543-8

Reference yield: 27.0%

nitrostyrene (5153-67-3) + (Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-ribofuranos-5-ylidene)amine N-oxide (191721-03-6) → (3R,4R,5S)-2-benzyl-3-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylotetrofuranos-4-yl)-4-nitro-5-phenylisoxazolidine + (3S,4S,5R)-2-benzyl-3-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylotetrofuranos-4-yl)-4-nitro-5-phenylisoxazolidine

Guidance literature:

In toluene; for 24h; Heating;

DOI:10.1016/S0957-4166(98)00488-1

upstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

N-benzylhydroxylamine hydrochloride

Downstream raw materials:

N-Benzyl-N-[(S)-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-hydroxylamine

N-Benzyl-N-[(R)-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-hydroxylamine

N-Benzyl-N-[(S)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-hydroxylamine

(E)-5,6-didehydro-5,6-dideoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-heptodialo-1,4-furanose

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