(2S,3R)-2-[(Benzyloxy)methyl]-3-methyloxirane

Base Information

• Chemical Name: (2S,3R)-2-[(Benzyloxy)methyl]-3-methyloxirane
• CAS No.: 72229-17-5
• Molecular Formula: C11H14O2
• Molecular Weight: 178.231
• DSSTox Substance ID: DTXSID40508111
• Mol file: 72229-17-5.mol

Synonyms:72229-17-5;(2S,3R)-2-[(Benzyloxy)methyl]-3-methyloxirane;DTXSID40508111

Chemical Property of (2S,3R)-2-[(Benzyloxy)methyl]-3-methyloxirane

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 178.099379685
• Heavy Atom Count: 13
• Complexity: 152

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(O1)COCC2=CC=CC=C2
• Isomeric SMILES: C[C@@H]1[C@@H](O1)COCC2=CC=CC=C2

Technology Process of (2S,3R)-2-[(Benzyloxy)methyl]-3-methyloxirane

There total 26 articles about (2S,3R)-2-[(Benzyloxy)methyl]-3-methyloxirane 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: 93.0%

((2R,3R)-3-methyloxiran-2-yl)methanol (58845-50-4,26097-34-7) + benzyl bromide (100-39-0) → (S)-3-benzyloxymethyl-2,2-dimethyloxirane (72229-17-5,72258-18-5,80374-36-3,80374-37-4,85200-35-7,116296-88-9,121470-06-2,131487-18-8,85165-52-2)

Guidance literature:

((2R,3R)-3-methyloxiran-2-yl)methanol; With sodium hydride; In tetrahydrofuran; at 0 ℃;

benzyl bromide; With potassium iodide; In tetrahydrofuran; for 72h;

DOI:10.1016/j.tetlet.2012.02.067

Reference yield: 90.7%

((2S,3R)-3-methyloxiran-2-yl)methanol (84823-48-3,26097-34-7) + benzyl bromide (100-39-0) → (2S,3R)-2-[(benzyloxy)methyl]-3-methyloxirane (72229-17-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.tet.2013.07.026

Reference yield: 87.0%

(2S,3S)-2,3-epoxy-1-butanol (50468-21-8,26097-34-7) + benzyl bromide (100-39-0) → (S)-3-benzyloxymethyl-2,2-dimethyloxirane (72229-17-5,72258-18-5,80374-36-3,80374-37-4,85200-35-7,116296-88-9,121470-06-2,131487-18-8,85165-52-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 ℃; for 6h; Inert atmosphere;

DOI:10.1002/anie.201410371

upstream raw materials:

Benzoic acid (1R,2R)-3-benzyloxy-1-methyl-2-(toluene-4-sulfonyloxy)-propyl ester

Toluene-4-sulfonic acid (1S,2S)-3-benzyloxy-2-hydroxy-1-methyl-propyl ester

Benzoic acid (1R,2R)-1-benzyloxymethyl-2-hydroxy-propyl ester

Benzoic acid (1R,2R)-3-benzyloxy-2-hydroxy-1-methyl-propyl ester

Downstream raw materials:

(2R,3R)-1-(benzyloxy)-3-methyl-5-trimethylsilylpent-4-yn-2-ol

(2R,3R)-1-(benzyloxy)-3-methylhex-5-en-2-ol

1-(benzyloxy)-3-methylbutan-2-ol

(2R,3S)-1-Benzyloxy-3-methyl-heptan-2-ol