(2S,3S)-3-azido-3-phenylpropane-1,2-diol

Base Information

• Chemical Name: (2S,3S)-3-azido-3-phenylpropane-1,2-diol
• CAS No.: 116911-14-9
• Molecular Formula: C9H11 N3 O2
• Molecular Weight: 193.205
• DSSTox Substance ID: DTXSID10151577
• Nikkaji Number: J3.352.687C
• Wikidata: Q83018055
• Mol file: 116911-14-9.mol

Synonyms:1,2-Propanediol,3-azido-3-phenyl-, [S-(R*,R*)]- (9CI); (2S,3S)-3-Azido-3-phenyl-1,2-propanediol

Chemical Property of (2S,3S)-3-azido-3-phenylpropane-1,2-diol

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 193.085126602
• Heavy Atom Count: 14
• Complexity: 210

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C(CO)O)N=[N+]=[N-]
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H]([C@@H](CO)O)N=[N+]=[N-]

Technology Process of (2S,3S)-3-azido-3-phenylpropane-1,2-diol

There total 5 articles about (2S,3S)-3-azido-3-phenylpropane-1,2-diol 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: 98.0%

3-phenyl-(2R,3R)-oxiran-2-ylmethanol (98819-68-2) → (2S,3S)-3-azido-3-phenyl-propane-1,2-diol (116911-14-9)

Guidance literature:

With sodium azide; water; ammonium chloride; In methanol; at 65 ℃; for 5h;

DOI:10.1016/j.tetasy.2007.04.006

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (2S,3S)-3-azido-3-phenyl-propane-1,2-diol (116911-14-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / (2S,3S)-(-)-diisopropyl tartrate; activated molecular sieves 4 Angstroem; TBHP / Ti(Oi-Pr)4 / CH₂Cl₂ / 3.5 h / -20 °C

2: 98 percent / NaN₃; NH₄Cl; H₂O / methanol / 5 h / 65 °C

With tert.-butylhydroperoxide; sodium azide; 4 A molecular sieve; water; ammonium chloride; titanium(IV) isopropylate; In methanol; dichloromethane; 1: Sharpless asymmetric epoxidation;

DOI:10.1016/j.tetasy.2007.04.006

Reference yield:

(4R,5R)-4-Benzyloxymethyl-5-phenyl-[1,3]dioxolan-2-one → (2S,3S)-3-azido-3-phenyl-propane-1,2-diol (116911-14-9)

Guidance literature:

With sodium azide; water; In N,N-dimethyl-formamide; at 110 ℃; for 24h;

DOI:10.1016/0040-4039(96)00534-5

upstream raw materials:

3-phenyl-(2R,3R)-oxiran-2-ylmethanol

(2E)-3-phenyl-2-propen-1-ol

(2S,3R)-2,3-epoxy-3-phenylpropan-1-ol

Downstream raw materials:

(S)-2-azido-2-phenylacetic acid

(2S,3S)-3-azido-2-((methylsulfonyl)oxy)-3-phenylpropyl pivalate

(2R)-2-[(S)-azido(phenyl)methyl]oxirane

L 733060