111465-44-2

Usage

Chemical Class

Spiro compounds
Spiro compounds are a class of organic compounds that contain a ring system of oxygen atoms.

Structure

Complex and unique
The compound has a complex and unique structure, which may contribute to its potential applications in medicinal and pharmaceutical fields.

Functional Groups

Ethyl group and hydroxy group
The presence of an ethyl group and a hydroxy group suggests potential for use in medicinal and pharmaceutical applications.

Stereochemistry

(3R,4S,6S,9R) designation
The stereochemistry of the compound is indicated by the (3R,4S,6S,9R) designation, which describes the arrangement of its four chiral centers.

Chiral Centers

Four chiral centers
The compound has four chiral centers, which are carbon atoms with four different substituents attached.

Potential Applications

Drug candidate or organic synthesis
Due to its unique structure and functional groups, 1,7-Dioxaspiro[5.5]undecane-3-methanol,9-ethyl-4-hydroxy-, (3R,4S,6S,9R)may have potential as a drug candidate or for use in organic synthesis.

Molecular Weight

174.23 g/mol
The molecular weight is the sum of the atomic weights of all the atoms in the molecule.

Solubility

Unknown
The solubility of the compound is not provided in the material, but it may vary depending on the solvent used.

Stability

Unknown
The stability of the compound is not provided in the material, but it may be influenced by factors such as temperature, pressure, and the presence of other chemicals.

Upstream product

• 96239-87-1 Toluene-4-sulfonic acid (3R,6R,9R,10S)-9-benzyloxymethyl-10-hydroxy-1,7-dioxa-spiro[5.5]undec-3-ylmethyl ester 
• 15990-74-6 3-ethyl-3,4-dihydro-2H-pyran 
• 594-19-4 tert.-butyl lithium 
• 90475-38-0 2,2-dimethy-5-oxiranyl-1,3-dioxane 
• 2583-25-7 allylmalonic acid 
• 87970-12-5 <3α,4β,6α(R^*)>-4-hydroxy-1,7-dioxaspiro<5.5>undecane-3,9-dimethanol 
• 132775-91-8 (2R)-2-ethyl-6-(trimethylsilyl)-4-hexyn-1-ol 
• 132775-87-2 (E)-(R)-2-Ethyl-6-trimethylsilanyl-hex-4-en-1-ol 
• 121363-54-0 (3R*,4R*,6R*,9R*)-3-<(t-butyldimethyl)siloxy>methyl-9-ethyl-1,7-dioxaspiro<5.5>undecan-4-ol 
• 121363-53-9 (3R*,4S*,5S*,6R*,9R*)-3-<(t-butyldimethyl)siloxy>methyl-5-chloro-9-ethyl-1,7-dioxaspiro<5.5>undecan-4-ol 
• 121363-52-8 (3R*,6R*,9R*)-3-<(t-butyldimethyl)siloxy>methyl-9-ethyl-1,7-dioxaspiro<5.5>undec-4-ene 
• 121363-48-2 (3S*,6R*,9R*)- and (3R*,6R*,9R*)-9-ethyl-3-hydroxymethyl-1,7-dioxaspiro<5.5>undec-4-ene 
• 121363-54-0 (3S*,4R*,6R*,9R*)-3-<(t-butyldimethyl)siloxy>methyl-9-ethyl-1,7-dioxaspiro<5.5>undecan-4-ol 
• 132775-95-2 (4S,6R,9R)/(4R,6S,9R)-9-ethyl-4-hydroxy-3-(hydroxymethyl)-1,7-dioxaspiro<5.5>undec-2-ene 

Downstream Products

• 83720-10-9 talaromycin A 
• 83720-10-9 (-)-talaromycin B 
• 106763-16-0 talaromycin A 12-(3',5'-dinitrobenzoate) 
• 106763-16-0 3-(9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecyl)methyl (3',5'-dinitro)benzoate 
• 83720-10-9 talaromycin C 
• 83720-10-9 talaromycin E 
• 83720-10-9 talaromycin F 
• 83720-10-9 talaromycin B 
• 83720-10-9 talaromycin G 
• 113195-31-6 C₂₆H₂₆N₄O₁₄ 
• 106763-16-0 3-(9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecyl)methyl (3',5'-dinitro)benzoate 
• 106763-16-0 3-(9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecyl)methyl (3',5'-dinitro)benzoate 
• 83780-27-2 (-)-Talaromycin B 

Relevant academic research and scientific papers

A Synthesis of Talaromycin B

The nucleophilic cleavage of the oxirane (4) by the organocuprate derived from 6-lithio-3-ethyl-3,4-dihydro-2H-pyran (3) was the key step in a synthesis of racemic talaromycin B (7).

Enantioselective Total Synthesis of the Mycotoxin (-)-Talaromycin B by a Hetero Diels-Alder Reaction

(-)-Talaromycin B was formed in an overall yield of 5 percent in nine steps via a hetero Diels-Alder reaction of the exocyclic vinyl ether 3 and methyl O-benzoyldiformylacetate (4) as the key transformation.The enantiomerically pure vinyl ether 3 was prep

Synthesis of Talaromycins A, B, C, and E

The synthesis of 2,2-diethyl-5-ethynyl-1,3-dioxane (9) is reported in an overall yield of 27percent from diethyl malonate.Addition of 5-ethyl tetrahydropyran-2-one to the lithium anion of (9) gave the hydroxy ketoacetylene (10) which was converted in four steps to the olefinic spiroacetals (19) and (20), which were obtained in a ratio of 2:1.The individual olefinic spiroacetals (19) and (20) gave access to the (+/-)-talomycins A and C, and B and E via a chlorohydration, reductive dechlorination, and deprotection sequence.

SYNTHESIS OF (+/-)-TALAROMYCINS A, B, C AND E

Two key unsaturated spiroacetals have been used in the synthesis of talaromycins A, B, C and E by routes involving chlorohydration and reductive dechlorination.

SYNTHESIS OF (-)-TALAROMYCINS A AND B

Highly enantiomerically pure (-)-talaromycins A and B undecane> were synthesized starting from chiral building blocks of microbial origin.

New Synthetic Route to Spiroacetals. The 3,4-Dihydro-2H-pyran Approach to (+/-)-Talaromycin B

The nucleophylic cleavage of the oxirane (9) by the organocuprate derived from 3-ethyl-6-lithio-3,4-dihydro-2H-pyran (7) was the key step in a synthesis of racemic talaromycin B (12).A similar synthesis of desethyltalaromycin B (15) from (9) and 6-lithio-

DIASTEREOTOPIC SELECTIVITY AT PROCHIRAL CARBON CENTERS. A STEREODIVERGENT SYNTHESIS OF THE TALAROMYCINS.

The transformation of the acyclic precursor previously employed in the synthesis of talaromycin B to the stereoisomeric avian toxin talaromycin A is described.Diastereotopic selectivity at prochiral carbon centers in an acetonide migration and in a subseq

Synthesis of (-)-Talaromycin A

The spiroketal talaromycin A has been prepared in high optical and diastereomeric purity by using a -sigmatropic (Wittig) rearrangement and a -Claisen rearrangement as key steps in controlling absolute configuration.

SPIROKETALS: A TOTAL SYNTHESIS OF (+/-)-TALAROMYCIN B VIA A STEREOSELECTIVE CATION-OLEFIN CYCLISATION STEP

The acid catalysed rearrangement of an acetal derived from 2-hydroxymethyl-3-butene-1-ol proceeding via an intramolecular cation-olefin cyclisation provides acces to a 4-hydroxytetrahydropyran and thence to (+/-)-talaromycin B.

NOC Approach to Spiroketals. A Total Synthesis of (+/-)-Talaromycin B

A total synthesis of the unqiue spiroketal natural product talaromycin B (1) is reported.This molecule, produced in nature by the toxicogenic fungus Talaromyces stipitatus, was constructed in the laboratory from the isoxazoline 6 generated (formula) on reacting the oxime 4 with the olefin 5 in the presence of NaOCl/Et3N/H20/CH2Cl2.The synthesis scheme is sufficiently flexible and efficient so as to be of practical use in the preparation of suitable quantities of this material for biological evaluation.