1,5-Anhydro-2,3-dideoxy-D-erythro-hex-2-enitol 4,6-Diacetate

Base Information

• Chemical Name: 1,5-Anhydro-2,3-dideoxy-D-erythro-hex-2-enitol 4,6-Diacetate
• CAS No.: 92131-91-4
• Molecular Formula: C₁₀H₁₄O₅
• Molecular Weight: 214.218
• Mol file: 92131-91-4.mol

Synonyms:

Chemical Property of 1,5-Anhydro-2,3-dideoxy-D-erythro-hex-2-enitol 4,6-Diacetate

Chemical Property:

• Boiling Point: 285.3±40.0 °C(Predicted)
• Density: 1.17±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

1,5-Anhydro-2,3-dideoxy-D-erythro-hex-2-enitol4,6-Diacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1,5-Anhydro-2,3-dideoxy-D-erythro-hex-2-enitol 4,6-Diacetate is used in the synthesis of novel tetrahydropyran-based dipeptide isosters, used towards the synthesis of topoisomerase inhibitors. Also used in the synthesis of D-allosamine derivatives.

Technology Process of 1,5-Anhydro-2,3-dideoxy-D-erythro-hex-2-enitol 4,6-Diacetate

There total 6 articles about 1,5-Anhydro-2,3-dideoxy-D-erythro-hex-2-enitol 4,6-Diacetate 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: 100.0%

D-glucal triacetate (2873-29-2) → ((2R,3S)-3-acetoxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate (149342-25-6,92131-91-4)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.25h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b01925

Reference yield: 95.0%

ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside (3323-72-6) → ((2R,3S)-3-acetoxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate (149342-25-6,92131-91-4)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; Ambient temperature;

DOI:10.1016/0008-6215(84)85099-5

Reference yield: 79.0%

((2R,3S)-3-acetoxy-6-hydroxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate (92131-90-3) → ((2R,3S)-3-acetoxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate (149342-25-6,92131-91-4)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; Ambient temperature;

DOI:10.1016/0008-6215(84)85099-5

upstream raw materials:

((2R,3S)-3-acetoxy-6-hydroxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate

ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside

D-glucal triacetate

4'-methoxyphenyl 4,6-di-O-acetyl-2,3-dideoxy-1-O-α-D-erythro-hex-2-enopyranoside

Refernces

• 1、 Alami, Mouad,Franco, Rémi,Gandon, Vincent,Ghouilem, Juba,Messaoudi, Samir,Retailleau, Pascal. "Regio- And diastereoselective Pd-catalyzed synthesis of C2-aryl glycosides". supporting information. p. 7175 - 7178. Retrieved 2020/07/14.
• 2、 Srinivas, Avula,Karthik, Pulluri,Sunitha, Malladi,Reddy, Koduri Vasumathi. "Microwave-assisted synthesis and anticancer activity of triazolyl thiazolidine derivatives of pyrene". . p. 700 - 710. Retrieved 2019/10/14.