(alphaS,2S)-alpha-[(Phenylmethoxy)methyl]-2-oxiranemethanol

Base Information

• Chemical Name: (alphaS,2S)-alpha-[(Phenylmethoxy)methyl]-2-oxiranemethanol
• CAS No.: 72229-12-0
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23
• DSSTox Substance ID: DTXSID801223643
• Mol file: 72229-12-0.mol

Synonyms:SCHEMBL10618787;DTXSID801223643;(alphaS,2S)-alpha-[(Phenylmethoxy)methyl]-2-oxiranemethanol;72229-12-0

Chemical Property of (alphaS,2S)-alpha-[(Phenylmethoxy)methyl]-2-oxiranemethanol

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 194.094294304
• Heavy Atom Count: 14
• Complexity: 166

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(O1)C(COCC2=CC=CC=C2)O
• Isomeric SMILES: C1[C@H](O1)[C@H](COCC2=CC=CC=C2)O

Technology Process of (alphaS,2S)-alpha-[(Phenylmethoxy)methyl]-2-oxiranemethanol

There total 30 articles about (alphaS,2S)-alpha-[(Phenylmethoxy)methyl]-2-oxiranemethanol 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: 100.0%

(2R,3S)-p-nitrobenzoesaeure-(1-benzyloxy-3,4-epoxy-2-butyl)ester (72229-14-2) → (R)-2-(benzyloxy)-1-((S)-oxiran-2-yl)ethanol (72229-15-3,72229-12-0,72229-13-1,78469-89-3,130321-87-8)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; methanol; at 10 - 15 ℃; for 2.5h;

DOI:10.1002/hlca.19810640311

Reference yield: 91.0%

(2S,3S)-p-nitrobenzoesaeure-(1-benzyloxy-3,4-epoxy-2-butyl)ester (78492-26-9) → (2S,3S)-1-benzyloxy-3-hydroxy-4-benzyloxybutane (72229-12-0)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; methanol; at 10 ℃; for 1.08333h;

DOI:10.1002/hlca.19810640311

Reference yield: 66.0%

(S)-1-(benzyloxy)but-3-en-2-ol (109613-59-4) → (R)-2-(benzyloxy)-1-((S)-oxiran-2-yl)ethanol (72229-15-3,72229-12-0,72229-13-1,78469-89-3,130321-87-8)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate; In dichloromethane; at -20 - 4 ℃; for 26h; Inert atmosphere; Molecular sieve;

DOI:10.1002/ejoc.201101549

upstream raw materials:

cis-4-benzyloxy-2,3-epoxy-1-butanol

2-phenyl-4,7-dihydro-1,3-dioxepine

(Z)-4-benzyloxy-but-2-en-1-ol

benzaldehyde

Downstream raw materials:

(2S,3S)-1-Benzyloxy-4-dimethylamino-butane-2,3-diol

C₁₇H₂₈O₄Si

C₂₁H₃₂O₅

C₂₁H₃₂O₅