(1S,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol

Base Information

• Chemical Name: (1S,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol
• CAS No.: 194220-59-2
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.336
• Mol file: 194220-59-2.mol

Synonyms:(1S,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol

Chemical Property of (1S,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol

Chemical Property:

Purity/Quality:

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MSDS Files:

Useful:

Technology Process of (1S,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol

There total 3 articles about (1S,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol 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: 90.0%

(1S,2S,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1-O-p-nitrobenzoyl-1,2,3-cyclopentanetriol → (1S,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol (194220-59-2)

Guidance literature:

With sodium methylate; In methanol; for 0.5h; Heating;

DOI:10.1016/S0957-4166(97)00236-X

Reference yield: 26.0%

(1S,2S,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1-O-p-nitrobenzoyl-1,2,3-cyclopentanetriol → (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (155899-66-4) + (1S,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol (194220-59-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 48h; Heating;

DOI:10.1016/S0957-4166(97)00236-X

Reference yield:

5-deoxy-5-iodo-2,3-O-isopropylidene-D-ribose O-benzyl oxime ether → (1S,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol (194220-59-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / HSnBu₃, AIBN / toluene / 0.5 h / Heating

2: 78 percent / Ph₃P, DEAD / tetrahydrofuran / 0.5 h / Heating

3: 26 percent / LiAlH₄ / tetrahydrofuran / 48 h / Heating

With lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene;

DOI:10.1016/S0957-4166(97)00236-X

Downstream raw materials:

(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol