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

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.

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 
• 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 
• 77-76-9 2,2-dimethoxy-propane 
• 77-95-2 D-(-)-quinic acid 
• 32384-42-2 (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone 
• 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 
• 101769-63-5 (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester 
• 138-59-0 shikimic acid 
• 1446467-07-7 C₁₃H₁₇F₃O₇S 
• 108-05-4 vinyl acetate 
• 102919-04-0 benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside 
• 64-17-5 ethanol 

Downstream Products

• 158341-64-1 (3R,4S,5S)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid 
• 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 
• 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.