(2R,3S)-2-((1S,2R,3R)-4-Azido-1,2,3-tris-benzyloxy-butyl)-3-(3-chloro-propyl)-oxirane

Base Information

• Chemical Name: (2R,3S)-2-((1S,2R,3R)-4-Azido-1,2,3-tris-benzyloxy-butyl)-3-(3-chloro-propyl)-oxirane
• CAS No.: 180467-28-1
• Molecular Formula: C₃₀H₃₄ClN₃O₄
• Molecular Weight: 536.071
• Mol file: 180467-28-1.mol

Synonyms:

Chemical Property of (2R,3S)-2-((1S,2R,3R)-4-Azido-1,2,3-tris-benzyloxy-butyl)-3-(3-chloro-propyl)-oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2-((1S,2R,3R)-4-Azido-1,2,3-tris-benzyloxy-butyl)-3-(3-chloro-propyl)-oxirane

There total 5 articles about (2R,3S)-2-((1S,2R,3R)-4-Azido-1,2,3-tris-benzyloxy-butyl)-3-(3-chloro-propyl)-oxirane 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:

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)-2-((1S,2R,3R)-4-Azido-1,2,3-tris-benzyloxy-butyl)-3-(3-chloro-propyl)-oxirane (180467-28-1)

Guidance literature:

Multi-step reaction with 4 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

3: 1.) 4percent OsO₄, N-methylmorfoline N-oxide, 2.) 10percent sodium bisulfite / 1.) THF, t-BuOH, H₂O, 72 h, 2.) 30 min

4: 1.) MsCl, Et₃N, 2.) NaH / 1.) CH₂Cl₂, -50 deg C, 1 h, 2.) THF/DMSO (10:1), room temperature, 12 h

With osmium(VIII) oxide; hydrogen azide; potassium hexamethylsilazane; sodium hydride; sodium hydrogensulfite; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In benzene;

DOI:10.1021/jo960609b

Reference yield:

(Z)-(2R,3S,4R)-2,3,4-tris(benzyloxy)-9-chloro-5-nonen-1-ol (154813-30-6) → (2R,3S)-2-((1S,2R,3R)-4-Azido-1,2,3-tris-benzyloxy-butyl)-3-(3-chloro-propyl)-oxirane (180467-28-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / hydrazoic acid, PPh₃, diethyl azodicarboxylate / benzene / 0.42 h / Ambient temperature

2: 1.) 4percent OsO₄, N-methylmorfoline N-oxide, 2.) 10percent sodium bisulfite / 1.) THF, t-BuOH, H₂O, 72 h, 2.) 30 min

3: 1.) MsCl, Et₃N, 2.) NaH / 1.) CH₂Cl₂, -50 deg C, 1 h, 2.) THF/DMSO (10:1), room temperature, 12 h

With osmium(VIII) oxide; hydrogen azide; sodium hydride; sodium hydrogensulfite; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In benzene;

DOI:10.1021/jo960609b

Reference yield:

(2R,3S,4R,5Z)-1-azido-2,3,4-tri(benzyloxy)-9-chloro-5-nonene (154813-31-7) → (2R,3S)-2-((1S,2R,3R)-4-Azido-1,2,3-tris-benzyloxy-butyl)-3-(3-chloro-propyl)-oxirane (180467-28-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 4percent OsO₄, N-methylmorfoline N-oxide, 2.) 10percent sodium bisulfite / 1.) THF, t-BuOH, H₂O, 72 h, 2.) 30 min

2: 1.) MsCl, Et₃N, 2.) NaH / 1.) CH₂Cl₂, -50 deg C, 1 h, 2.) THF/DMSO (10:1), room temperature, 12 h

With osmium(VIII) oxide; sodium hydride; sodium hydrogensulfite; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine;

DOI:10.1021/jo960609b

upstream 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

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

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

Downstream raw materials:

(1S,7R,8R,9R,9aS)-7,8,9-Tris-benzyloxy-octahydro-quinolizin-1-ol