(1R,4R,5S)-(-)-1-azido-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene

Base Information

• Chemical Name: (1R,4R,5S)-(-)-1-azido-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene
• CAS No.: 89291-78-1
• Molecular Formula: C₁₆H₁₉N₃O₃
• Molecular Weight: 301.345
• Mol file: 89291-78-1.mol

Synonyms:(1R,4R,5S)-(-)-1-azido-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene

Chemical Property of (1R,4R,5S)-(-)-1-azido-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4R,5S)-(-)-1-azido-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene

There total 14 articles about (1R,4R,5S)-(-)-1-azido-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene 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: 84.0%

(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol methanesulfonate (89291-77-0) → (1R,4R,5S)-(-)-1-azido-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene (89291-78-1)

Guidance literature:

With lithium azide; In N,N,N,N,N,N-hexamethylphosphoric triamide; dimethyl sulfoxide; at 24 ℃; for 16h;

DOI:10.1016/S0040-4039(00)94140-6

Reference yield:

(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol (89291-76-9) → (1R,4R,5S)-(-)-1-azido-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene (89291-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / Et₃N / CH₂Cl₂ / 0.17 h / -5 - 0 °C

2: 74 percent / LiN₃, P(NMe₂)3 / dimethylsulfoxide / Ambient temperature

With lithium azide; triethylamine; Hexamethylphosphorous triamide; In dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jo00259a019

Reference yield:

(3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one (117307-62-7,89291-75-8) → (1R,4R,5S)-(-)-1-azido-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene (89291-78-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.17 h / 0 - 5 °C

2: 100 percent / Et₃N / CH₂Cl₂ / 0.17 h / -5 - 0 °C

3: 74 percent / LiN₃, P(NMe₂)3 / dimethylsulfoxide / Ambient temperature

With sodium tetrahydroborate; cerium(III) chloride; lithium azide; triethylamine; Hexamethylphosphorous triamide; In methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jo00259a019

upstream raw materials:

(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol methanesulfonate

2,3-O-isopropylidene-D-ribonic-γ-lactone

benzyl bromide

(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol

Downstream raw materials:

neplanocin A

(1R,4R,5S)-(-)-1-<(5-amino-6-chloropyrimidinyl)amino>-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene

(-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>adenine

(-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine