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

Base Information

• Chemical Name: (2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxycycloheptanone
• CAS No.: 1352406-29-1
• Molecular Formula: C₂₂H₂₅N₃O₄
• Molecular Weight: 395.458
• Mol file: 1352406-29-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxycycloheptanone 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: 95.0%

(1R,2R,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxycycloheptan-1-ol (1352406-28-0) → (2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxycycloheptanone (1352406-29-1)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.carres.2011.10.025

Reference yield:

C29H30O5 → (2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxycycloheptanone (1352406-29-1)

Guidance literature:

Multi-step reaction with 6 steps

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

1.2: 2 h / 0 - 20 °C

2.1: 2,4,6-trimethyl-pyridine / dichloromethane / 1.5 h / 20 °C

3.1: methanol; sodium methylate / Inert atmosphere

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

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h

6.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

With 2,4,6-trimethyl-pyridine; methanol; borane-THF; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; sodium methylate; Dess-Martin periodane; triphenylphosphine; In tetrahydrofuran; dichloromethane; 3.1: Zemplen deacylation / 4.1: Mitsunobu type reaction;

DOI:10.1016/j.carres.2011.10.025

Reference yield:

(3R,4S,5R)-3-O-benzyloxy-4-O-p-methoxybenzyloxy-5-O-triisopropylsilyloxycycloheptan-1-ol → (2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxycycloheptanone (1352406-29-1)

Guidance literature:

Multi-step reaction with 3 steps

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

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h

3: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; Dess-Martin periodane; triphenylphosphine; In tetrahydrofuran; dichloromethane; 1: Mitsunobu type reaction;

DOI:10.1016/j.carres.2011.10.025

upstream raw materials:

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

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

Downstream raw materials:

(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

Refernces