3,4-O-(DiethylMethylidene) ShikiMic Acid Ethyl Ester

Base Information

• Chemical Name: 3,4-O-(DiethylMethylidene) ShikiMic Acid Ethyl Ester
• CAS No.: 943515-58-0
• Molecular Formula: C₁₄H₂₂O₅
• Molecular Weight: 270.326
• Mol file: 943515-58-0.mol

Synonyms:(3aR,7R,7aS)-ethyl 2,2-diethyl-7-hydroxy-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate

Chemical Property of 3,4-O-(DiethylMethylidene) ShikiMic Acid Ethyl Ester

Chemical Property:

• Boiling Point: 384.1±42.0 °C(Predicted)
• PKA: 13.40±0.60(Predicted)
• Density: 1.132±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

3,4-O-(Diethylmethylidene)ShikimicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 3,4-O-(Diethylmethylidene) Shikimic Acid Ethyl Ester is a reactant used in the preparation of oseltamivir analogs as neuraminidase inhibitors against avian influenza virus.

Technology Process of 3,4-O-(DiethylMethylidene) ShikiMic Acid Ethyl Ester

There total 13 articles about 3,4-O-(DiethylMethylidene) ShikiMic Acid Ethyl Ester 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: 92.8%

(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester (101769-63-5) + 3,3-diethoxypentane (36749-09-4) → (3aR,7R,7aS)-ethyl 2,2-diethyl-7-hydroxy-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate (943515-58-0)

Guidance literature:

In ethanol; at 20 ℃; for 2h;

Reference yield: 92.0%

ethyl (R)-4-((4S,5R)-2,2-diethyl-5-vinyl-1,3-dioxolan-4-yl)-4-hydroxy-2-methylenebutanoate → (3aR,7R,7aS)-ethyl 2,2-diethyl-7-hydroxy-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate (943515-58-0)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In 1,2-dichloro-ethane; for 2h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2016.02.044

Reference yield: 75.0%

(3aR,7S,7aR)-ethyl 2,2-diethyl-7-(trifluoromethylsulfonyloxy)-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate (1346667-84-2) → (3aR,7R,7aS)-ethyl 2,2-diethyl-7-hydroxy-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate (943515-58-0)

Guidance literature:

With sodium nitrite; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3.5h;

DOI:10.1016/j.tetlet.2011.09.035

upstream raw materials:

(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester

3,3-diethoxypentane

methyl 2,3-O-isopentylidene-β-D-ribofuranose

methyl 5-deoxy-5-iodo-2,3-O-isopentylidene-β-D-ribofuranose

Downstream raw materials:

oseltamivir

oseltamivir phosphate

(3R,4S,5S)-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-4-hydroxycyclohex-1-enecarboxylic acid ethyl ester

(3R,4S,5S)-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-4-trifluoromethanesulfonyloxycyclohex-1-enecarboxylic acid ethyl ester

Refernces

• 1、 Kumar, Bejugam Santhosh,Mishra, Girija Prasad,Rao, Batchu Venkateswara. "Synthesis of some carbahexopyranoses using Mn/CrCl3 mediated domino reactions and ring closing metathesis". . p. 1838 - 1849. Retrieved 2017/03/10.
• 2、 Kongkamnerd, Jarinrat,Cappelletti, Luca,Prandi, Adolfo,Seneci, Pierfausto,Rungrotmongkol, Thanyada,Jongaroonngamsang, Nutthapon,Rojsitthisak, Pornchai,Frecer, Vladimir,Milani, Adelaide,Cattoli, Giovanni,Terregino, Calogero,Capua, Ilaria,Beneduce, Luca,Gallotta, Andrea,Pengo, Paolo,Fassina, Giorgio,Miertus, Stanislav,De-Eknamkul, Wanchai. "Synthesis and in vitro study of novel neuraminidase inhibitors against avian influenza virus". supporting information; experimental part. p. 2152 - 2157. Retrieved 2012/05/05.