(+/-)-cis-2-methyl-3-(benzoyloxy)-2,3-dihydropyrone

Base Information

• Chemical Name: (+/-)-cis-2-methyl-3-(benzoyloxy)-2,3-dihydropyrone
• CAS No.: 91861-10-8
• Molecular Formula: C₁₃H₁₂O₄
• Molecular Weight: 232.236
• Mol file: 91861-10-8.mol

Synonyms:(+/-)-cis-2-methyl-3-(benzoyloxy)-2,3-dihydropyrone

Chemical Property of (+/-)-cis-2-methyl-3-(benzoyloxy)-2,3-dihydropyrone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-cis-2-methyl-3-(benzoyloxy)-2,3-dihydropyrone

There total 2 articles about (+/-)-cis-2-methyl-3-(benzoyloxy)-2,3-dihydropyrone 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: 70.0%

acetaldehyde (75-07-0,9002-91-9) + Benzoic acid (1Z,3E)-2-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-buta-1,3-dienyl ester (143362-43-0) → (+/-)-cis-2-methyl-3-(benzoyloxy)-2,3-dihydropyrone (91861-10-8) + (+/-)-trans-2-methyl-3-(benzoyloxy)-2,3-dihydropyrone (91861-11-9)

Guidance literature:

zinc(II) chloride; In tetrahydrofuran; for 24h; Product distribution; Ambient temperature; various catalysts;

DOI:10.1021/ja00291a028

Reference yield: 44.0%

acetaldehyde (75-07-0,9002-91-9) + Benzoic acid (1Z,3E)-2-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-buta-1,3-dienyl ester (143362-43-0) → (+/-)-cis-2-methyl-3-(benzoyloxy)-2,3-dihydropyrone (91861-10-8)

Guidance literature:

tris{3-(heptafluoropropylhydroxymethylene)-(+)-camphorato}europium(III); In chloroform-d1; for 48h; Ambient temperature;

DOI:10.1021/ja00291a028

Reference yield:

(+/-)-cis-2-methyl-3-(benzoyloxy)-2,3-dihydropyrone (91861-10-8) → (+/-)-methyl 3-O-acetyl-4-O-benzoyl-2,6-dideoxy-β-lyxo-hexopyranoside (91861-19-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) mercuric acetate (Hg(OAc)2); 2.) sodium cyanoborohydride (NaCNBH₃) / 1.) room temp., 24 h; 2.) methanol, -78 deg C, 2.5 h

2: 62 percent / K-Selectride / tetrahydrofuran / 2 h / -78 °C

3: 90 percent / triethylamine / 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h

With mercury(II) diacetate; sodium cyanoborohydride; potassium tri-sec-butyl-borohydride; triethylamine; dmap; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00291a028

upstream raw materials:

acetaldehyde

Benzoic acid (1Z,3E)-2-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-buta-1,3-dienyl ester

Downstream raw materials:

(+/-)-methyl-4-O-benzoyl-2,6-dideoxy-β-threo-hexopyranosid-3-ulose

methyl 2,3,4-tri-O-acetyl-6-deoxy-α-DL-galactopyranoside

(+/-)-methyl 4-O-benzoyl-2,6-dideoxy-β-lyxo-hexopyranoside

(+/-)-methyl 3-O-acetyl-4-O-benzoyl-2,6-dideoxy-β-lyxo-hexopyranoside