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
• Mol file: 136994-78-0.mol

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

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:

>95% ^*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 → ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate (136994-78-0)

Guidance literature:

With sodium tetrahydroborate; In ethyl acetate; at 0 - 20 ℃; for 2h;

DOI:10.1002/ejoc.202100653

Reference yield: 88.0%

(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester (101769-63-5) + 2,2-dimethoxy-propane (77-76-9) → ethyl (3aR,7R,7aS)-2,2-dimethyl-7-hydroxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate (136994-78-0)

Guidance literature:

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

Reference yield: 49.4%

vinyl acetate (108-05-4,9003-20-7) + ethyl 5-hydroxy-3,4-isopropylidenedioxycyclohex-1-enecarboxylate → C14H20O6 (1446467-05-5) + ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate (136994-78-0)

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

upstream raw materials:

2-(Diethoxy-phosphoryl)-3-((3aS,4R,6aS)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionic acid ethyl ester

benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside

(E)-3-((3aS,4R,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-acrylic acid ethyl ester

vinyl acetate

Downstream raw materials:

(3R,4S,5S)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid

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

ethyl (3R,4R,5R)-3-(1-ethyl-propoxy)-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate

Refernces

• 1、 -. "Synthesis method of daphenanthrene key intermediate". . . Retrieved 2020/06/20.
• 2、 -. "Cyclohexenes derivative or its pharmaceutically acceptable salts and its use". Page/Page column 13. . Retrieved 2016/10/09.