ETHYL 4,6-DI-O-ACETYL-2,3-DIDEOXY-ALPHA-D-ERYTHRO-HEX-2-ENOPYRANOSIDE

Base Information

• Chemical Name: ETHYL 4,6-DI-O-ACETYL-2,3-DIDEOXY-ALPHA-D-ERYTHRO-HEX-2-ENOPYRANOSIDE
• CAS No.: 3323-72-6
• Molecular Formula: C12H18 O6
• Molecular Weight: 258.271
• Hs Code.: 2932999099
• Mol file: 3323-72-6.mol

Synonyms:D-erythro-Hex-2-enopyranoside,ethyl 2,3-dideoxy-, diacetate, a- (8CI); a-D-erythro-Hex-2-enopyranoside,ethyl 2,3-dideoxy-, diacetate (9CI); Ethyl 4,6-di-O-acetyl-2,3-dideoxy-a-D-erythro-hex-2-enopyranoside;Ethyl-4,6-di-O-acetyl-2,3-dideoxy-a-D-erythrohex-2-enopyranoside; Ethyl-4,6-di-O-acetyl-a-y-D-glucal

Chemical Property of ETHYL 4,6-DI-O-ACETYL-2,3-DIDEOXY-ALPHA-D-ERYTHRO-HEX-2-ENOPYRANOSIDE

Chemical Property:

• Vapor Pressure: 0.000123mmHg at 25°C
• Melting Point: 77-79 °C(lit.)
• Boiling Point: 335.1°Cat760mmHg
• Flash Point: 145.2°C
• PSA: 71.06000
• Density: 1.16g/cm³
• LogP: 0.79880
• Solubility.: methylene chloride: 0.1 g/mL, clear

Purity/Quality:

99.90% ^*data from raw suppliers

(+)-Ethyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside forsynthesis ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ETHYL 4,6-DI-O-ACETYL-2,3-DIDEOXY-ALPHA-D-ERYTHRO-HEX-2-ENOPYRANOSIDE

There total 29 articles about ETHYL 4,6-DI-O-ACETYL-2,3-DIDEOXY-ALPHA-D-ERYTHRO-HEX-2-ENOPYRANOSIDE 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: 99.0%

ethanol (64-17-5) + D-glucal triacetate (2873-29-2) → ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside (3323-72-6)

Guidance literature:

With iodine; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.3987/COM-10-12043

Reference yield: 93.0%

2'-iodoethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (142544-41-0,142544-42-1) → 4,6-di-O-acetyl-1,2,3-trideoxy-2',3',4',5'-tetrahydro-α,β-D-ribo-hexopyranoso<1,2-b>furan (121237-55-6) + ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside (3323-72-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium cyanoborohydride; In tert-butyl alcohol; for 0.5h; Heating;

Reference yield: 91.0%

ethanol (64-17-5) + D-glucal triacetate (2873-29-2) → ethyl 4, 6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside (3323-72-6,56196-39-5,61826-47-9,63976-48-7,69055-68-1,78148-04-6) + ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside (3323-72-6)

Guidance literature:

With tellurium tetrachloride; In dichloromethane; at 0 - 20 ℃; for 0.416667h; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2012.09.073

upstream raw materials:

2-bromoethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Acetic acid (2R,3S)-2-acetoxymethyl-6-(2-bromo-ethoxy)-3,6-dihydro-2H-pyran-3-yl ester

2'-iodoethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

acrylic acid methyl ester

Downstream raw materials:

ethyl 6-O-acetyl-4-(N-benzyl)methylamino-2,3,4-trideoxy-β-D-erythro-hex-2-enopyranoside

ethyl 2,3-dideoxy-4-O-diphenylphosphino-6-O-trityl-α-D-threo-hex-2-enopyranoside

ethyl 2,3-dideoxy-α-D-threo-hex-2-enopyranoside

ethyl 2,3-dideoxy-6-O-trityl-α-D-threo-hex-2-enopyranoside

Refernces

• 1、 Princiotto, Salvatore,Di Bussolo, Valeria,Bordoni, Vittorio,Favero, Lucilla,Crotti, Stefano,Uccello Barretta, Gloria,Balzano, Federica,Crotti, Paolo. "Stereoselective synthesis of D-galactal-derived N-ethoxycarbonyl aziridine, as a new, improved synthetic protocol to glycal-derived N-activated vinyl aziridines". . p. 829 - 837. Retrieved 2017.
• 2、 Yadav, Ram Naresh,Banik, Indrani,Banik, Bimal Krishna. "Montmorillonite-catalyzed glysosylation of alcohols with glycals derived from galactose and glucose under microwave-induced reactions". . p. 1385 - 1387. Retrieved 2020/06/27.