136994-78-0

Basic information

• Product Name: ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate
• Synonyms: ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate
• CAS NO: 136994-78-0
• Molecular Weight: 242.272
• Mol File: 136994-78-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 55-58°C
• Boiling Point: 356.6±42.0 °C(Predicted)
• Density: 1.190±0.06 g/cm3(Predicted)
• CAS DataBase Reference: ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate(136994-78-0)
• EPA Substance Registry System: ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate(136994-78-0)

Safety Data

• Hazardous Substances Data: 136994-78-0(Hazardous Substances Data)

Usage

Description

Ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate, also known as Ethyl 3,4-O-isopropylideneshikimate, is a chemical compound derived from shikimate, a central intermediate in the biosynthesis of aromatic amino acids in plants and microorganisms. It is characterized by its unique structure, featuring an isopropylidenedioxy group and a hydroxyl group, which contribute to its chemical properties and potential applications.

Uses

Used in Pharmaceutical Industry:
Ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate is used as an intermediate in the synthesis of Oseltamivir phosphate (O701000), an orally active inhibitor of influenza virus neuraminidase. This antiviral drug is effective in treating and preventing influenza A and B infections, making it a valuable compound in the pharmaceutical industry for addressing public health concerns related to viral outbreaks.
Used in Synthesis of Other Compounds:
Due to its unique structure, ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate can also be used as a building block or intermediate in the synthesis of other complex organic compounds with potential applications in various fields, such as agrochemicals, materials science, and specialty chemicals. Its versatility in chemical reactions allows for the development of novel compounds with specific properties and functions.

Upstream product

• 136994-76-8 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 
• 102919-04-0 benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside 
• 136994-75-7 (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 
• 108-05-4 vinyl acetate 
• 1446467-07-7 C₁₃H₁₇F₃O₇S 
• 138-59-0 shikimic acid 
• 101769-63-5 (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester 
• 77-76-9 2,2-dimethoxy-propane 
• 64-17-5 ethanol 
• 42411-62-1 (3aR,4R,7S,8aR)-2,2-dimethyl-6-oxotetrahydro-4,7-methano[1,3]dioxolo[4,5-c]oxepin-7(6H)-yl methanesulfonate 
• 141-52-6 sodium ethanolate 
• 32384-42-2 (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone 
• 77-95-2 D-(-)-quinic acid 

Downstream Products

• 101769-63-5 (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester 
• 204254-92-2 ethyl (3R,4R,5R)-3-(1-ethyl-propoxy)-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate 
• 204254-90-0 ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate 
• 204254-84-2 ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate 
• 158341-64-1 (3R,4S,5S)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid 
• 90927-40-5 (3R,4S,5S)-5-hydroxy-3,4-(isopropylidenedioxy)cyclohex-1-enecarboxylic acid 

Relevant articles and documents

Stereodivergent Syntheses of All Stereoisomers of (?)-Shikimic Acid: Development of a Chiral Pool for the Diverse Polyhydroxy-cyclohexenoid (or -cyclohexanoid) Bioactive Molecules

Novel stereodivergent total syntheses of all the seven stereoisomers of (?)-shikimic acid [(?)-SA 1] have been systematically performed. (+)-ent-SA ent-1 was synthesized from (?)-SA 1 via 9 steps in 31 % overall yield; (?)-3-epi-SA 2 was synthesized from (?)-SA 1 via 5 steps in 66 % overall yield; (+)-3-epi-ent-SA ent-2 was synthesized from (?)-SA 1 via 7 steps in 43 % overall yield; (?)-4-epi-SA 3 was synthesized from (?)-SA 1 via 11 steps in 32 % overall yield; (+)-4-epi-ent-SA ent-3 was synthesized from (?)-SA 1 via 7 steps in 42 % overall yield; (?)-5-epi-SA 4 was synthesized from (?)-SA 1 via 6 steps in 56 % overall yield; and (+)-5-epi-ent-SA ent-4 was synthesized from (?)-SA 1 via 12 steps in 29 % overall yield. The stereochemistry of all the above seven stereoisomers of (?)-SA 1 were further studied by two dimensional (2D) 1H NMR technique.

Synthesis method of daphenanthrene key intermediate

The invention relates to a synthetic method of a Duffy key intermediate. The synthetic method comprises the following steps of by taking shikimic acid as a starting material and performing reactions including esterification reaction, selective oxidation a

Chemo-enzymatic enantioconvergent approach toward ethyl shikimate from ethyl 5-hydroxy-3,4-isopropylidenedioxycyclohex-1-enecarboxylate

An enantioconvergent route for natural form of ethyl shikimate was achieved from Diels-Alder adduct of furan and acryloyl chloride. The key step was a highly enantioselective (E >500) and efficient acetylation of ethyl (3R*,4S*,5S*)-5-hydroxy-3,4-isopropylidenedioxycyclohex-1- enecarboxylate, which had a diastereomeric relationship with ethyl shikimate, mediated by Burkholderia cepacia lipase (Amano PS-IM). Both of the resolved enantiomers were converted to natural form of ethyl shikimate by inversion at C-5 for the former and at C-3 and C-4 for the latter, respectively.