(1S,2S,3R,5S)-4-O-benzylhydroxylamino-5-iodo-2,3-O-isopropylidene-1,2-cyclopentanediol

Base Information

• Chemical Name: (1S,2S,3R,5S)-4-O-benzylhydroxylamino-5-iodo-2,3-O-isopropylidene-1,2-cyclopentanediol
• CAS No.: 194220-50-3
• Molecular Formula: C₁₅H₂₀INO₃
• Molecular Weight: 389.233
• Mol file: 194220-50-3.mol

Synonyms:(1S,2S,3R,5S)-4-O-benzylhydroxylamino-5-iodo-2,3-O-isopropylidene-1,2-cyclopentanediol

Chemical Property of (1S,2S,3R,5S)-4-O-benzylhydroxylamino-5-iodo-2,3-O-isopropylidene-1,2-cyclopentanediol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,5S)-4-O-benzylhydroxylamino-5-iodo-2,3-O-isopropylidene-1,2-cyclopentanediol

There total 2 articles about (1S,2S,3R,5S)-4-O-benzylhydroxylamino-5-iodo-2,3-O-isopropylidene-1,2-cyclopentanediol 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: 69.0%

(1R,2R,3S,4R)-4-(benzyloxyamino)-2,3-O-isopropylidenecyclopentane-1,2,3-triol (138946-55-1) → (1S,2S,3R,5S)-4-O-benzylhydroxylamino-5-iodo-2,3-O-isopropylidene-1,2-cyclopentanediol (194220-50-3)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene; for 24h; 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,2S,3R,5S)-4-O-benzylhydroxylamino-5-iodo-2,3-O-isopropylidene-1,2-cyclopentanediol (194220-50-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 69 percent / I₂, Ph₃P, imidazole / toluene / 24 h / Heating

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; triphenylphosphine; In toluene;

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

Reference yield: 91.0%

(1S,2S,3R,5S)-4-O-benzylhydroxylamino-5-iodo-2,3-O-isopropylidene-1,2-cyclopentanediol (194220-50-3) → (1R,2S,3R)-3-O-benzylhydroxylamino-1,2-O-isopropylidene-cyclopent-4-en-1,2-diol

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 14h; Heating;

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

upstream raw materials:

(1R,2R,3S,4R)-4-(benzyloxyamino)-2,3-O-isopropylidenecyclopentane-1,2,3-triol