104010-72-2

Basic information

• Product Name: (+)-(3AS,6AS)-3A,6A-DIHYDRO-2,2-DIMETHYL-4H-CYCLOPENTA-1,3-DIOXOL-4-ONE
• Synonyms: (+)-(3AS,6AS)-3A,6A-DIHYDRO-2,2-DIMETHYL-4H-CYCLOPENTA-1,3-DIOXOL-4-ONE;(3aS,6aS)-2,2-diMethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one;(3aS,6aS)-2,2-dimethyl-2H,3aH,4H,6aH-cyclopenta[d][1,3]dioxol-4-one
• CAS NO: 104010-72-2
• Molecular Formula: C₈H₁₀O₃
• Molecular Weight: 154.16
• Product Categories: pharmacetical
• Mol File: 104010-72-2.mol
• Article Data: 31

Chemical Properties

• Melting Point: 68.1-69.4 °C
• Boiling Point: 243.842°C at 760 mmHg
• Flash Point: 91.74°C
• Appearance: /
• Density: 1.157g/cm³
• Vapor Pressure: 0.031mmHg at 25°C
• Refractive Index: 1.482
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: (+)-(3AS,6AS)-3A,6A-DIHYDRO-2,2-DIMETHYL-4H-CYCLOPENTA-1,3-DIOXOL-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(3AS,6AS)-3A,6A-DIHYDRO-2,2-DIMETHYL-4H-CYCLOPENTA-1,3-DIOXOL-4-ONE(104010-72-2)
• EPA Substance Registry System: (+)-(3AS,6AS)-3A,6A-DIHYDRO-2,2-DIMETHYL-4H-CYCLOPENTA-1,3-DIOXOL-4-ONE(104010-72-2)

Safety Data

• Hazardous Substances Data: 104010-72-2(Hazardous Substances Data)

Usage

Uses

(+)-(3aS,6aS)-3a,6a-Dihydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-one is an intermediate in the synthesis of Queuine (Q525000), the modified base which is found at first anticodon position of specific tRNAs.

InChI:InChI=1/C8H10O3/c1-8(2)10-6-4-3-5(9)7(6)11-8/h3-4,6-7H,1-2H3/t6-,7+/m0/s1

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 192181-38-7 (3aR,6aS)-2,2-Dimethyl-4-oct-(E)-ylidene-4,6a-dihydro-3aH-cyclopenta[1,3]dioxole 
• 524939-64-8 (1S,4S,5S)-(+)-4,5-O-isopropylidene-1-hydroxymethyl-2-cyclopenten-1-ol 
• 524939-65-9 (1R,4S,5S)-(+)-4,5-O-isopropylidene-1-hydroxymethyl-2-cyclopenten-1-ol 
• 57702-56-4 cis- and trans-4-cumyloxy-2-cyclopentenol 
• 103056-56-0 (+/-)-cis-4-phenyloxy-2-cyclopenten-1-ol 
• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 
• 196497-20-8 (1R,5S,8R)-8-methoxy-3,3-dimethyl-2,4,7-trioxabicyclo[3.3.0]octan-6-one 
• 1092971-27-1 C₂₁H₃₄NO₄⁽¹⁺⁾*I^(1-) 
• 1092971-26-0 C₂₄H₃₂NO₄⁽¹⁺⁾*I^(1-) 
• 67-68-5 dimethyl sulfoxide 
• 6991-65-7 (3aR,4R,6aS)-4-methoxy-2,2-dimethyl-6-methylenetetrahydrofuro[3,4-d][1,3]dioxole 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 104832-18-0 (4R,5R)-2,2-Dimethyl-5-[2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-[1,3]dioxolane-4-carboxylic acid methyl ester 

Downstream Products

• 180524-82-7 (+)-(1S,4S,5S)-4,5-dihydroxy-4,5-O-isopropylidene-1-(p-methoxybenzyloxy)methylcyclopent-2-en-1-ol 
• 869476-97-1 (3aS,6aS)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-one 
• 910138-89-5 C₂₅H₂₃NO₆ 
• 910138-85-1 C₂₈H₂₉NO₇ 
• 910138-86-2 C₂₅H₂₅NO₇ 
• 910138-81-7 C₃₁H₃₅NO₈S 
• 910138-88-4 C₃₀H₃₁NO₉ 
• 38750-57-1 (-)-Cephalotaxinone 
• 36804-95-2 deoxyharringtonine 
• 683276-45-1 4,5-dihydroxy-2-prop-(Z)-enyl-cyclopent-2-enone 
• 683276-45-1 4,5-dihydroxy-2-prop-(E)-enyl-cyclopent-2-enone 
• 683276-31-5 (3aS,6aS)-2,2-dimethyl-5-prop-(Z)-enyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 
• 683276-30-4 (3aS,6aS)-2,2-dimethyl-5-prop-(E)-enyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 
• 72877-50-0 neplanocin A 

Relevant articles and documents

Studies on the Synthesis of (-)-Neplanocin A. Homochiral Preparation of a Key Cyclopentanoid Intermediate

-

Synthesis of the transfer-RNA nucleoside queuosine by using a chiral allyl azide intermediate

Chilled out: Chiral allyl azides are rarely used in natural product synthesis because of their tendency to undergo a [3.3] sigmatropic rearrangement (see scheme, top). In allylic cyclopentenyl azides, this rearrangement can be suppressed at just 0°C, enabling a short convergent synthesis of the hypermodified transfer-RNA nucleoside queuosine. (Chemical Equation Presented).

Improved and alternative synthesis of D- and L-cyclopentenone derivatives, the versatile intermediates for the synthesis of carbocyclic nucleosides

Improved and alternative syntheses of D- and L-cyclopentenone derivatives were achieved in six steps from D-ribose via ring-closing metathesis (RCM) reaction as a key step. These derivatives serve as very versatile intermediates for the synthesis of carbocyclic nucleosides.

Antiviral activity of cyclopentenyl nucleosides against orthopox viruses (smallpox, monkeypox and cowpox)

An improved method for the synthesis of enantiomerically pure D-cyclopentenyl nucleosides has been accomplished and their antiviral activity against orthopox viruses have been evaluated. The key intermediate, L-cyclopent-2-enone 13 was prepared from D-ribose using a ring closing metathesis reaction in eight steps. Among the synthesized nucleosides, the adenine 2 (Neplanocin A), cytosine 14, and 5-F-cytosine 15 analogues exhibited potent anti-orthopox virus activity, including smallpox virus.

EFFICIENT ENANTIOSELECTIVE SYNTHESES OF CARBOCYCLIC NUCLEOSIDE AND PROSTAGLANDIN SYNTHONS

Simple and efficient enantioselective syntheses of two hydroxylated cyclopentenones, 2 and 10, which are useful intermediates for the synthesis of various carbocyclic nucleosides and prostaglandins, directly from readily available sugars are described.

USE OF THE IRRITATING PRINCIPAL OLEOCANTHAL IN OLIVE OIL, AS WELL AS STRUCTURALLY AND FUNCTIONALLY SIMILAR COMPOUNDS

The invention provides oleocanthal analogs and methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.

USE OF THE IRRITATING PRINCIPAL OLEOCANTHAL IN OLIVE OIL, AS WELL AS STRUCTURALLY AND FUNCTIONALLY SIMILAR COMPOUNDS

The invention provides methods of synthesizing the purified enantiomers of oleocanthal. The invention further provides methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.