(1S,2S,3S,4S,5R)-4-benzylamino-5-(hydroxymethyl)-1,2-isopropylidenecyclopentane-1,2,3-triol

Base Information

Chemical Name:(1S,2S,3S,4S,5R)-4-benzylamino-5-(hydroxymethyl)-1,2-isopropylidenecyclopentane-1,2,3-triol
CAS No.:732308-58-6
Molecular Formula:C₁₆H₂₃NO₄
Molecular Weight:293.363
Hs Code.:

Synonyms:(1S,2S,3S,4S,5R)-4-benzylamino-5-(hydroxymethyl)-1,2-isopropylidenecyclopentane-1,2,3-triol

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Chemical Property of (1S,2S,3S,4S,5R)-4-benzylamino-5-(hydroxymethyl)-1,2-isopropylidenecyclopentane-1,2,3-triol

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Technology Process of (1S,2S,3S,4S,5R)-4-benzylamino-5-(hydroxymethyl)-1,2-isopropylidenecyclopentane-1,2,3-triol

There total 20 articles about (1S,2S,3S,4S,5R)-4-benzylamino-5-(hydroxymethyl)-1,2-isopropylidenecyclopentane-1,2,3-triol 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: 100.0%

: 732308-57-5
(1S,2S,3S,4S,5R)-4-benzylamino-3-O-4-N-(oxomethylidene)-1,2-O-isopropylidene-5-((tert-butyl-dimethylsilyloxy)methyl)cyclopentane-1,2,3-triol

: 732308-58-6
(1S,2S,3S,4S,5R)-4-benzylamino-5-(hydroxymethyl)-1,2-isopropylidenecyclopentane-1,2,3-triol

Guidance literature:: With sodium hydroxide; In ethanol; at 60 ℃; for 7h;
DOI:10.1039/b315704k

Reference yield: 64.0%

: 855517-47-4
(1S,2S,3S,4S,5S)-4-N-benzyl-5-acetoxymethyl-7,8-isopropylidenedioxy-2-oxa-4-azabicyclo[3.3.0]oct-3-one

: 732308-58-6
(1S,2S,3S,4S,5R)-4-benzylamino-5-(hydroxymethyl)-1,2-isopropylidenecyclopentane-1,2,3-triol

Guidance literature:: With sodium hydroxide; In ethanol; at 65 ℃; for 2h;
DOI:10.1039/b501824b

Reference yield:

: (3aR,6R,6aR)-6-Benzyloxy-4,5-dihydroxy-hexahydro-cyclopenta[b]furan-2-one

: 732308-58-6
(1S,2S,3S,4S,5R)-4-benzylamino-5-(hydroxymethyl)-1,2-isopropylidenecyclopentane-1,2,3-triol

Guidance literature:: Multi-step reaction with 10 steps

1: 180 mg / H₂SO₄ / acetone / 0.5 h / 25 °C

2: 88 percent / DIBAL-H / CH₂Cl₂ / 1.5 h / -78 °C

3: 62 percent / (diacetoxyiodo)benzene; I₂ / cyclohexane / 0.67 h / 25 °C / Irradiation

4: 60.7 percent / aq. Na₂CO₃ / methanol / 2.5 h / 25 °C

5: 61 percent / dimethylformamide / 65 °C

6: 87 percent / pyridine; DMAP / CH₂Cl₂ / 25 °C

7: 90.4 percent / H₂ / Pd/C / methanol; ethyl acetate / 25 °C

8: 95.7 percent / Et₃N / CH₂Cl₂ / 25 °C

9: 71.5 percent / t-BuOK / tetrahydrofuran / 0.58 h / 25 °C

10: 64 percent / aq. NaOH / ethanol / 2 h / 65 °C

With pyridine; dmap; sodium hydroxide; [bis(acetoxy)iodo]benzene; sulfuric acid; potassium tert-butylate; hydrogen; iodine; diisobutylaluminium hydride; sodium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; cyclohexane; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1039/b501824b