(2R,3S,4R,5Z)-1-azido-2,3,4-tri(benzyloxy)-9-chloro-5-nonene

Base Information

• Chemical Name: (2R,3S,4R,5Z)-1-azido-2,3,4-tri(benzyloxy)-9-chloro-5-nonene
• CAS No.: 154813-31-7
• Molecular Formula: C₃₀H₃₄ClN₃O₃
• Molecular Weight: 520.071
• Mol file: 154813-31-7.mol

Synonyms:(2R,3S,4R,5Z)-1-azido-2,3,4-tri(benzyloxy)-9-chloro-5-nonene

Chemical Property of (2R,3S,4R,5Z)-1-azido-2,3,4-tri(benzyloxy)-9-chloro-5-nonene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5Z)-1-azido-2,3,4-tri(benzyloxy)-9-chloro-5-nonene

There total 2 articles about (2R,3S,4R,5Z)-1-azido-2,3,4-tri(benzyloxy)-9-chloro-5-nonene 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%

(Z)-(2R,3S,4R)-2,3,4-tris(benzyloxy)-9-chloro-5-nonen-1-ol (154813-30-6) → (2R,3S,4R,5Z)-1-azido-2,3,4-tri(benzyloxy)-9-chloro-5-nonene (154813-31-7)

Guidance literature:

With tris-(2-chloro-ethyl)-amine; triphenylphosphine; diethylazodicarboxylate; In benzene; at 0 - 20 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)61395-3

Reference yield:

2,3,4-tri-O-benzyl-D-arabinopyranose (18039-26-4,20787-16-0,20787-21-7,77943-32-9,77943-33-0,89615-43-0,89615-44-1,90899-55-1) → (2R,3S,4R,5Z)-1-azido-2,3,4-tri(benzyloxy)-9-chloro-5-nonene (154813-31-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) potassium bis(trimethylsilil)amide / 1.) THF, toluene, 0 deg C, 30 min, 2.) THF, -78 -> 0 deg C, 6 h

2: 84 percent / hydrazoic acid, PPh₃, diethyl azodicarboxylate / benzene / 0.42 h / Ambient temperature

With hydrogen azide; potassium hexamethylsilazane; triphenylphosphine; diethylazodicarboxylate; In benzene;

DOI:10.1021/jo960609b

Reference yield: 88.0%

(2R,3S,4R,5Z)-1-azido-2,3,4-tri(benzyloxy)-9-chloro-5-nonene (154813-31-7) → (2R,3R)-2-((1S,2R,3R)-4-Azido-1,2,3-tris-benzyloxy-butyl)-3-(3-chloro-propyl)-oxirane

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1016/S0040-4039(00)61395-3

upstream raw materials:

(Z)-(2R,3S,4R)-2,3,4-tris(benzyloxy)-9-chloro-5-nonen-1-ol

2,3,4-tri-O-benzyl-D-arabinopyranose

Downstream raw materials:

(4R,5R,6R,7R,8R)-9-Azido-6,7,8-tris-benzyloxy-1-chloro-nonane-4,5-diol

(4S,5S,6R,7R,8R)-9-Azido-6,7,8-tris-benzyloxy-1-chloro-nonane-4,5-diol

(3R,4R,5R)-3,4,5-Tris-benzyloxy-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-4-chloro-butyl]-2,3,4,5-tetrahydro-pyridine

(2R,3R,4R,5S,6R)-1-Azido-2,3,4-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-9-chloro-nonan-5-ol