ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate

Base Information

Chemical Name:ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate
CAS No.:136994-78-0
Molecular Formula:C₁₂H₁₈O₅
Molecular Weight:242.272
Hs Code.:

Synonyms:ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate

Suppliers and Price of ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
Ethyl3,4-O-isopropylideneshikimate
500mg
$ 185.00

Medical Isotopes, Inc.
Ethyl3,4-O-isopropylideneshikimate
1 g
$ 650.00

Total 7 raw suppliers

Chemical Property of ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate

Chemical Property:

Melting Point:55-58°C
Boiling Point:356.6±42.0 °C(Predicted)
Density:1.190±0.06 g/cm3(Predicted)

Purity/Quality:

>98% ^*data from raw suppliers

Ethyl3,4-O-isopropylideneshikimate ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Uses Ethyl 3,4-O-isopropylideneshikimate is an acetonide used in the synthesis of Oseltamivir phosphate (O701000), an orally active inhibitor of influenza virus neuraminidase; converted in vivo to the active acid metabolite. An antiviral drug.

Technology Process of ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate

There total 14 articles about ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-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: 93.0%

: ethyl (3R,4R)-3,4-isopropylidenedioxy-5-oxo-cyclohex-1-ene-1-carboxylate

: 136994-78-0
ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate

Guidance literature:: With sodium tetrahydroborate; In ethyl acetate; at 0 - 20 ℃; for 2h;
DOI:10.1002/ejoc.202100653

Reference yield: 88.0%

: 101769-63-5
(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester

: 77-76-9
2,2-dimethoxy-propane

: 136994-78-0
ethyl (3aR,7R,7aS)-2,2-dimethyl-7-hydroxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate

Guidance literature:: With toluene-4-sulfonic acid; In ethyl acetate; for 2h; under 112.511 - 150.015 Torr;

Reference yield: 49.4%

: 108-05-4,9003-20-7
vinyl acetate

: ethyl 5-hydroxy-3,4-isopropylidenedioxycyclohex-1-enecarboxylate

: 1446467-05-5
C₁₄H₂₀O₆

: 136994-78-0
ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate

Guidance literature:: With Burkholderia cepacia lipase (Amano PS-IM); at 20 ℃; for 8h; Reagent/catalyst; Time; enantioselective reaction; Enzymatic reaction;
DOI:10.1016/j.tet.2013.05.004