(3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-iodo-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

Base Information

• Chemical Name: (3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-iodo-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole
• CAS No.: 869711-17-1
• Molecular Formula: C₁₅H₁₈IN₃O₃
• Molecular Weight: 415.231

Synonyms:(3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-iodo-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

Chemical Property of (3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-iodo-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of (3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-iodo-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

There total 6 articles about (3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-iodo-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole 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: 92.0%

(3aS,4R,5R,6S,6aS)-4-Azido-6-benzyloxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-ol (869711-14-8) → (3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-iodo-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole (869711-17-1)

Guidance literature:

(3aS,4R,5R,6S,6aS)-4-Azido-6-benzyloxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-ol; With trifluoromethylsulfonic anhydride; In pyridine; dichloromethane;

With lithium iodide; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2005.08.163

Reference yield:

(1S,2S,5S)-5-Benzyloxy-cyclopent-3-ene-1,2-diol → (3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-iodo-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole (869711-17-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: mCPBA / CH₂Cl₂

2.1: NaN₃ / dimethylformamide; H₂O

3.1: pTSA / acetone

4.1: Tf₂O / pyridine; CH₂Cl₂

4.2: 92 percent / LiI / tetrahydrofuran

With sodium azide; trifluoromethylsulfonic anhydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tetlet.2005.08.163

Reference yield:

(2R,3S,4R)-4-Benzyloxy-6-oxa-bicyclo[3.1.0]hexane-2,3-diol → (3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-iodo-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole (869711-17-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaN₃ / dimethylformamide; H₂O

2.1: pTSA / acetone

3.1: Tf₂O / pyridine; CH₂Cl₂

3.2: 92 percent / LiI / tetrahydrofuran

With sodium azide; trifluoromethylsulfonic anhydride; toluene-4-sulfonic acid; In pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tetlet.2005.08.163

upstream raw materials:

(3aS,4R,5R,6S,6aS)-4-Azido-6-benzyloxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-ol

(3aR,4S,6aS)-4-Benzyloxy-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxole

benzyl bromide

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