(S)-methyl 2,3-dihydro-4H-pyran-4-one-2-carboxylate

Base Information

• Chemical Name: (S)-methyl 2,3-dihydro-4H-pyran-4-one-2-carboxylate
• CAS No.: 157493-03-3
• Molecular Formula: C₇H₈O₄
• Molecular Weight: 156.138
• Mol file: 157493-03-3.mol

Synonyms:

Chemical Property of (S)-methyl 2,3-dihydro-4H-pyran-4-one-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-methyl 2,3-dihydro-4H-pyran-4-one-2-carboxylate

There total 7 articles about (S)-methyl 2,3-dihydro-4H-pyran-4-one-2-carboxylate 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: 5.0%

(S)-2,4,4-trimethoxy-6-(o-methoxyphenyl)tetrahydropyran + diazomethyl-trimethyl-silane (18107-18-1) → (S)-methyl 2,3-dihydro-4H-pyran-4-one-2-carboxylate (157493-03-3,183013-60-7,333719-20-3)

Guidance literature:

(S)-2,4,4-trimethoxy-6-(o-methoxyphenyl)tetrahydropyran; With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 4h;

diazomethyl-trimethyl-silane; With methanol; In diethyl ether; at 20 ℃;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 12h;

Reference yield:

Methyl glyoxylate (922-68-9) + (E)-3-(tert-butyldimethylsilyloxy)-1-methoxy-1,3-butadiene (71735-01-8) → (2R)-2,3-dihydro-2-carbomethoxy-4H-pyran-4-one (183013-60-7,333719-20-3) + (S)-methyl 2,3-dihydro-4H-pyran-4-one-2-carboxylate (157493-03-3,183013-60-7,333719-20-3)

Guidance literature:

Methyl glyoxylate; (E)-3-(tert-butyldimethylsilyloxy)-1-methoxy-1,3-butadiene; (S,S)-(Bn-Phebox)RhCl₂(H₂O); In toluene; at -78 ℃; for 1h;

With trifluoroacetic acid; In toluene; at -78 - 0 ℃; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(00)01049-8

Reference yield:

Methyl glyoxylate (922-68-9) + 1-methoxy-3-<(trimethylsilyl)oxy>01,3-butadiene (59414-23-2) → (2R)-2,3-dihydro-2-carbomethoxy-4H-pyran-4-one (183013-60-7,333719-20-3) + (S)-methyl 2,3-dihydro-4H-pyran-4-one-2-carboxylate (157493-03-3,183013-60-7,333719-20-3)

Guidance literature:

Methyl glyoxylate; With C₂₅H₁₉N₃O₂*In⁽³⁺⁾*3I^(1-); In dichloromethane; for 2h; Inert atmosphere; Molecular sieve;

1-methoxy-3-<(trimethylsilyl)oxy>01,3-butadiene; In dichloromethane; at 20 ℃; Inert atmosphere; Molecular sieve;

With trifluoroacetic acid; In dichloromethane; at -20 ℃; for 3h; Overall yield = 61 %; enantioselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1021/ol400841s

upstream raw materials:

danishefsky's diene

Methyl glyoxylate

(E)-3-(tert-butyldimethylsilyloxy)-1-methoxy-1,3-butadiene

diazomethyl-trimethyl-silane