(2R,6R)-2-(3-Benzyloxy-propyl)-6-prop-2-ynyl-3,6-dihydro-2H-pyran

Base Information

• Chemical Name: (2R,6R)-2-(3-Benzyloxy-propyl)-6-prop-2-ynyl-3,6-dihydro-2H-pyran
• CAS No.: 194423-25-1
• Molecular Formula: C₁₈H₂₂O₂
• Molecular Weight: 270.371
• Mol file: 194423-25-1.mol

Synonyms:(2R,6R)-2-(3-Benzyloxy-propyl)-6-prop-2-ynyl-3,6-dihydro-2H-pyran

Chemical Property of (2R,6R)-2-(3-Benzyloxy-propyl)-6-prop-2-ynyl-3,6-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6R)-2-(3-Benzyloxy-propyl)-6-prop-2-ynyl-3,6-dihydro-2H-pyran

There total 7 articles about (2R,6R)-2-(3-Benzyloxy-propyl)-6-prop-2-ynyl-3,6-dihydro-2H-pyran 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: 97.0%

(2R,6R)-2-(3-Benzyloxy-propyl)-6-(3,3-dibromo-allyl)-3,6-dihydro-2H-pyran (1026393-78-1) → (2R,6R)-2-(3-Benzyloxy-propyl)-6-prop-2-ynyl-3,6-dihydro-2H-pyran (194423-25-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; 1) -78 deg C, 1.5 h; 2) 20 deg C, 1 h;

DOI:10.1021/jo970597+

Reference yield:

4-benzyloxybutanal (5470-84-8) → (2R,6R)-2-(3-Benzyloxy-propyl)-6-prop-2-ynyl-3,6-dihydro-2H-pyran (194423-25-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) (+)-Ipc₂BCl, N,N-diisopropylethylamine / 1) Et₂O, 0 deg C, 1.5 h; 2) Et₂O, -78 deg C, 1.5 h, -5 deg C, 18 h

2: N,N-diisopropylethylamine, TMSOTf / CH₂Cl₂ / 1) -78 deg C, 5 min; 2) 20 deg C, 1 h

3: CeCl₃*7H₂O, NaBH₄ / ethanol / 1 h / -78 °C

4: N,N-diisopropylethylamine, DMAP / CH₂Cl₂ / 16 h / 20 °C

5: 79 percent / Cl₂Ti(Oi-Pr)2 / toluene; CH₂Cl₂ / 1 h / -40 °C

6: 1.) Ph₃P, Zn dust / 1) CH₂Cl₂, 20 deg C, 66 h; 2) CH₂Cl₂, 40 h

7: 97 percent / n-BuLi / tetrahydrofuran; hexane / 1) -78 deg C, 1.5 h; 2) 20 deg C, 1 h

With dmap; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; titanium(IV) dichlorodiisopropylate; (+)-β-chlorodiisopinocampheylborane; trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene;

DOI:10.1021/jo970597+

Reference yield:

(R)-2-(3-Benzyloxy-propyl)-2,3-dihydro-pyran-4-one (194423-20-6) → (2R,6R)-2-(3-Benzyloxy-propyl)-6-prop-2-ynyl-3,6-dihydro-2H-pyran (194423-25-1)

Guidance literature:

Multi-step reaction with 5 steps

1: CeCl₃*7H₂O, NaBH₄ / ethanol / 1 h / -78 °C

2: N,N-diisopropylethylamine, DMAP / CH₂Cl₂ / 16 h / 20 °C

3: 79 percent / Cl₂Ti(Oi-Pr)2 / toluene; CH₂Cl₂ / 1 h / -40 °C

4: 1.) Ph₃P, Zn dust / 1) CH₂Cl₂, 20 deg C, 66 h; 2) CH₂Cl₂, 40 h

5: 97 percent / n-BuLi / tetrahydrofuran; hexane / 1) -78 deg C, 1.5 h; 2) 20 deg C, 1 h

With dmap; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; titanium(IV) dichlorodiisopropylate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene;

DOI:10.1021/jo970597+

upstream raw materials:

(2R,6R)-2-(3-Benzyloxy-propyl)-6-(3,3-dibromo-allyl)-3,6-dihydro-2H-pyran

4-benzyloxybutanal

(R)-2-(3-Benzyloxy-propyl)-2,3-dihydro-pyran-4-one

(2R,4S)-2-(3-Benzyloxy-propyl)-3,4-dihydro-2H-pyran-4-ol