(2R,3S)-4-(Benzyloxy)-2,3-epoxybutanal

Base Information

• Chemical Name: (2R,3S)-4-(Benzyloxy)-2,3-epoxybutanal
• CAS No.: 84573-21-7
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.214
• DSSTox Substance ID: DTXSID001182081
• Nikkaji Number: J1.173.589D
• Mol file: 84573-21-7.mol

Synonyms:DTXSID001182081;84573-21-7;(2R,3S)-4-(Benzyloxy)-2,3-epoxybutanal;rel-(2R,3S)-3-[(Phenylmethoxy)methyl]-2-oxiranecarboxaldehyde

Chemical Property of (2R,3S)-4-(Benzyloxy)-2,3-epoxybutanal

Chemical Property:

• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 192.078644241
• Heavy Atom Count: 14
• Complexity: 187

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC2C(O2)C=O
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@H]2[C@@H](O2)C=O

Technology Process of (2R,3S)-4-(Benzyloxy)-2,3-epoxybutanal

There total 3 articles about (2R,3S)-4-(Benzyloxy)-2,3-epoxybutanal 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: 85.0%

cis-4-benzyloxy-2,3-epoxy-1-butanol (87172-27-8) → (±)-3-((benzyloxy)methyl)oxirane-2-carbaldehyde (84573-21-7,87938-77-0,99945-63-8,113215-46-6,114925-54-1,127909-66-4,133321-78-5)

Guidance literature:

With dipyridinium dichromate; 4 A molecular sieve; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1016/0040-4039(94)85219-7

Reference yield:

(Z)-4-benzyloxy-but-2-en-1-ol (81028-03-7) → (±)-3-((benzyloxy)methyl)oxirane-2-carbaldehyde (84573-21-7,87938-77-0,99945-63-8,113215-46-6,114925-54-1,127909-66-4,133321-78-5)

Guidance literature:

Multi-step reaction with 2 steps

1: mCPBA

With 3-chloro-benzenecarboperoxoic acid; 2: Swern oxidation;

DOI:10.1039/b307390d

Reference yield:

benzyl bromide (100-39-0) → (±)-3-((benzyloxy)methyl)oxirane-2-carbaldehyde (84573-21-7,87938-77-0,99945-63-8,113215-46-6,114925-54-1,127909-66-4,133321-78-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / NaH / dimethylformamide / 5 h / -20 °C

2: 86 percent / MCPBA / CH₂Cl₂ / 12 h / 0 - 25 °C

3: 85 percent / PDC, 4 A molecular sieves / CH₂Cl₂ / 4 h / Ambient temperature

With dipyridinium dichromate; 4 A molecular sieve; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(94)85219-7

upstream raw materials:

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

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

benzyl bromide

Downstream raw materials:

(R)-1-((2S,3R)-3-Benzyloxymethyl-oxiranyl)-but-3-en-1-ol

2-(benzyloxy)-1-cyclopropyl-1-ethanol

1-Benzyloxy-penten-⁽³⁾-ol-⁽²⁾

Refernces

• 1、 Gnawali, Giri Raj,Rath, Nigam P.,Spilling, Christopher D.. "Synthesis of Phostones via the Palladium-Catalyzed Ring Opening of Epoxy Vinyl Phosphonates". . p. 8724 - 8730. Retrieved 2019/07/03.
• 2、 Righi, Giuliana,Pescatore, Giovanna,Bonadies, Francesco,Bonini, Carlo. "A study on the chelation control in the regioselective opening of 2,3-bifunctionalized epoxides". . p. 5649 - 5656. Retrieved 2007/10/03.