(1R,2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxy-1-O-triisopropylsilyloxycycloheptane

Base Information

• Chemical Name: (1R,2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxy-1-O-triisopropylsilyloxycycloheptane
• CAS No.: 1352406-27-9
• Molecular Formula: C₃₁H₄₇N₃O₄Si
• Molecular Weight: 553.817

Synonyms:(1R,2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxy-1-O-triisopropylsilyloxycycloheptane

Chemical Property of (1R,2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxy-1-O-triisopropylsilyloxycycloheptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (1R,2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxy-1-O-triisopropylsilyloxycycloheptane

There total 6 articles about (1R,2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxy-1-O-triisopropylsilyloxycycloheptane 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: 71.0%

(3R,4S,5R)-3-O-benzyloxy-4-O-p-methoxybenzyloxy-5-O-triisopropylsilyloxycycloheptan-1-ol → (1R,2S,3R,5S)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxy-1-O-triisopropylsilyloxycycloheptane (1352406-31-5) + (1R,2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxy-1-O-triisopropylsilyloxycycloheptane (1352406-27-9)

Guidance literature:

With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; optical yield given as %de;

DOI:10.1016/j.carres.2011.10.025

Reference yield:

(3R,4R)-4-O-benzyloxy-6-hydroxy-3-O-p-methoxybenzyloxynona-1,8-diene → (1R,2S,3R,5S)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxy-1-O-triisopropylsilyloxycycloheptane (1352406-31-5) + (1R,2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxy-1-O-triisopropylsilyloxycycloheptane (1352406-27-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine; dmap / 16 h / 20 °C

2.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 0.38 h / 80 °C / Microwave irradiation

3.1: borane-THF / tetrahydrofuran / 2 h / 0 °C

3.2: 2 h / 0 - 20 °C

4.1: 2,4,6-trimethyl-pyridine / dichloromethane / 1.5 h / 20 °C

5.1: methanol; sodium methylate / Inert atmosphere

6.1: di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran / 0 - 20 °C

With pyridine; 2,4,6-trimethyl-pyridine; methanol; dmap; Hoveyda-Grubbs catalyst second generation; borane-THF; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; sodium methylate; triphenylphosphine; In tetrahydrofuran; dichloromethane; 5.1: Zemplen deacylation / 6.1: Mitsunobu type reaction;

DOI:10.1016/j.carres.2011.10.025

Reference yield:

C31H34O5 → (1R,2S,3R,5S)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxy-1-O-triisopropylsilyloxycycloheptane (1352406-31-5) + (1R,2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxy-1-O-triisopropylsilyloxycycloheptane (1352406-27-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 0.38 h / 80 °C / Microwave irradiation

2.1: borane-THF / tetrahydrofuran / 2 h / 0 °C

2.2: 2 h / 0 - 20 °C

3.1: 2,4,6-trimethyl-pyridine / dichloromethane / 1.5 h / 20 °C

4.1: methanol; sodium methylate / Inert atmosphere

5.1: di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran / 0 - 20 °C

With 2,4,6-trimethyl-pyridine; methanol; Hoveyda-Grubbs catalyst second generation; borane-THF; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; sodium methylate; triphenylphosphine; In tetrahydrofuran; dichloromethane; 4.1: Zemplen deacylation / 5.1: Mitsunobu type reaction;

DOI:10.1016/j.carres.2011.10.025

Downstream raw materials:

(1R,2R,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxycycloheptan-1-ol

(2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxycycloheptanone

(1R,2S,3R,5R)-3-O-benzyloxy-2-O-p-methoxybenzyloxy-8-azabicyclo[3.2.1]octane-1-ol

(1R,2S,3R,5R)-8-azabicyclo[3.2.1]octane-1,2,3-triol

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