2-(3-methyloxiran-2-yl)-6-oxo-3,6-dihydro-2H-pyran-3-yl acetate (non-preferred name)

Base Information

• Chemical Name: 2-(3-methyloxiran-2-yl)-6-oxo-3,6-dihydro-2H-pyran-3-yl acetate (non-preferred name)
• CAS No.: 69651-03-2
• Molecular Formula: C10H12O5
• Molecular Weight: 212.1993
• Mol file: 69651-03-2.mol

Synonyms:

Chemical Property of 2-(3-methyloxiran-2-yl)-6-oxo-3,6-dihydro-2H-pyran-3-yl acetate (non-preferred name)

Chemical Property:

• Vapor Pressure: 2.23E-05mmHg at 25°C
• Boiling Point: 360.4°C at 760 mmHg
• Flash Point: 162.3°C
• Density: 1.28g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(3-methyloxiran-2-yl)-6-oxo-3,6-dihydro-2H-pyran-3-yl acetate (non-preferred name)

There total 23 articles about 2-(3-methyloxiran-2-yl)-6-oxo-3,6-dihydro-2H-pyran-3-yl acetate (non-preferred name) 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: 22.0%

Acetic acid (2R,3S)-2-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-propyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester (131696-26-9) → (+)-asperlin (14375-36-1,30387-51-0,57378-87-7,69651-03-2,69651-04-3,95042-47-0,95042-48-1,95042-49-2,95042-50-5,107741-13-9,111466-69-4,113665-99-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In dichloromethane; Ambient temperature;

DOI:10.1016/S0957-4166(00)82363-0

Reference yield: 20.0%

Acetic acid (2S,3R,6S)-6-ethoxy-2-((2R,3S)-3-methyl-oxiranyl)-3,6-dihydro-2H-pyran-3-yl ester (111397-89-8) → D-asperlin (69651-03-2)

Guidance literature:

With jones reagent; magnesium sulfate; In acetone; at 0 - 5 ℃; for 2h;

DOI:10.1139/v87-057

Reference yield:

L-rhamnose (73-34-7) → (+)-asperlin (14375-36-1,30387-51-0,57378-87-7,69651-03-2,69651-04-3,95042-47-0,95042-48-1,95042-49-2,95042-50-5,107741-13-9,111466-69-4,113665-99-9)

Guidance literature:

Multi-step reaction with 12 steps

1: Dowex-H⁽¹⁺⁾ / Heating

2: p-TsOH / dimethylformamide / Heating

3: 2,6-lutidine / CH₂Cl₂ / 0 °C

4: 90percent aq. AcOH

5: PCC-MS, molecular sieves 3A, NaOAc / CH₂Cl₂ / Ambient temperature

6: NaBH₄ / methanol / -78 °C

7: 95 percent / DCC / CH₂Cl₂ / Ambient temperature

8: BCl₃ / CH₂Cl₂ / -78 °C

9: Ag₂CO₃, H₂O / acetone / Ambient temperature

10: 32 percent / NaH / tetrahydrofuran / Ambient temperature

11: 64 percent / Et₃N / 0 - 20 °C

12: 22 percent / Bu₄NF*3H₂O / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; sodium tetrahydroborate; 3 A molecular sieve; Dowex-H⁽¹⁺⁾; tetrabutyl ammonium fluoride; water; sodium acetate; boron trichloride; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; silver carbonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0957-4166(00)82363-0

upstream raw materials:

Acetic acid (2R,3S)-2-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-propyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester

L-rhamnose

methyl 2,3-O-methylorthoacetyl-α-L-rhamnopyranoside

tert-Butyl-((3aR,4R,6S,7S,7aS)-2-ethoxy-4-methoxy-2,6-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-dimethyl-silane

Refernces

• 1、 Valverde,Herradon,Rabanal,Martin-Lomas. "The synthesis of D-asperlin". . p. 339 - 342. Retrieved 2007/10/02.