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Chemical Structure| 163226-45-7 Chemical Structure| 163226-45-7

Structure of 163226-45-7

Chemical Structure| 163226-45-7

(3AS,4S,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

CAS No.: 163226-45-7

4.5 *For Research Use Only !

Cat. No.: A354919 Purity: 95%

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Product Details of [ 163226-45-7 ]

CAS No. :163226-45-7
Formula : C28H28O4
M.W : 428.52
SMILES Code : O[C@H]1C=C(COC(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)[C@]5([H])[C@@]1([H])OC(C)(C)O5
MDL No. :MFCD30536586
InChI Key :HZWCKFPVWSCREB-NXCFDTQHSA-N
Pubchem ID :10884464

Safety of [ 163226-45-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 163226-45-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 163226-45-7 ]

[ 163226-45-7 ] Synthesis Path-Downstream   1~37

  • 1
  • [ 98-88-4 ]
  • [ 163226-45-7 ]
  • (1S,2S,3R)-1-benzoyloxy-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopentene [ No CAS ]
  • 2
  • [ 88559-56-2 ]
  • [ 163226-45-7 ]
YieldReaction ConditionsOperation in experiment
98% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h;Inert atmosphere; A solution of 57 22 (81mg, 0.19mmol) in 30 THF (2mL) was added dropwise to a suspension of 59 LAH (36mg, 0.96mmol) in THF (2mL) at 0C. After the reaction was stirred at rt for 2h, 60 H2O (1mL) was added to quench it. After the mixture was stirred at rt for 1h, 61 MgSO4 was added, and the resulting mixture was filtered through Celite and concentrated to give a residue, which was purified using silica gel column chromatography (EtOAc-hexane 1:3) to give 7 2alpha (79mg, 98%, white solid).16 2alpha: 1H NMR (300MHz, CDCl3): delta 1.36 (s, 3H), 1.37 (s, 3H), 2.74 (d, 1H, J=10.2Hz), 3.65 (dt, 1H, J=14.4, 1.8Hz), 3.88 (d, 1H, J=14.4Hz), 4.59 (br, 1H), 4.75 (t, 1H, J=5.4Hz), 4.88 (d, 1H, J=5.4Hz), 6.00 (br, 1H), 7.20-7.32 (m, 9H), 7.44-7.48 (m, 6H).
  • 3
  • [ 66224-66-6 ]
  • [ 163226-45-7 ]
  • (1S,2R,5R)-5-(6-Amino-purin-9-yl)-3-trityloxymethyl-cyclopent-3-ene-1,2-diol [ No CAS ]
  • 4
  • [ 66224-66-6 ]
  • [ 163226-45-7 ]
  • 9-((3aS,4R,6aR)-4,6a-dihydro-6-((trityloxy)methyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-6-amine [ No CAS ]
  • 5
  • [ 2770-01-6 ]
  • [ 163226-45-7 ]
  • [ 877651-81-5 ]
  • [ 877651-87-1 ]
YieldReaction ConditionsOperation in experiment
20%; 20% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -78 - 20℃; for 24h;Product distribution / selectivity; The chiral cyclopentenyl moiety 5 (below) was prepared from D-ribose in 8 steps following a previously reported synthetic method via a chiral induction, a regioselective protection of hydroxy group and ring-closing metathesis with 0.1 mole% of the 2nd generation Grubbs catalyst as key steps. 10; The other key intermediate 7 was synthesized according to the previously reported procedure11 from commercially available 4-amino-2-chloropyridine (6) in 4 steps (overall 54% yield) as shown in Scheme 1. Mitsunobu reaction of 7 with 5 provided a mixture of the N9- and N7-regioisomers (8:9 = 2:1) in 94% yield. The separation of the desired product (8) from the reaction mixture was difficult by silica gel column [isolated yields: 20% (8) and 20% (9), respectively]. The ratio of the two isomers was determined by 1H-NMR, and their configuration was identified by Nuclear Overhouser Effect (ID-NOE), which indicated the <n="38"/>interaction between the C1 '-H and the aromatic C3-H of compound 8, whereas the same effect was not present in compound 9.
  • 6
  • [ 934816-33-8 ]
  • [ 163226-45-7 ]
  • 7
  • [ 17325-26-7 ]
  • [ 163226-45-7 ]
  • [ 878479-17-5 ]
  • 8
  • [ 76-83-5 ]
  • [ 162126-83-2 ]
  • [ 163226-45-7 ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine;dmap; In dichloromethane; at 20℃; for 12h;Product distribution / selectivity; To a solution of compound 14 (1.0 g, 5.37 mmol), catalytic amount of DMAP (0.07 g, 0.54 mmol) and trityl chloride (1.90 g, 6.71 mmol) in 20 mL of anhydrous DCM, Et3N (1.0 mL, 6.71 mmol) was added at room temperature under N2 atmosphere. After 12 hr at room temperature, the reaction mixture was poured into ice water (20 mL). The product was extracted with CH2Cl2 (20 mL x 3) from aqueous layer. The combined solution washed with saturated aqueous NH4Cl (10 mL x 2), water (20 mL) and brine (10 mL x 2) and then dried over Na2SO4, filtered, concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane: EtOAc = 20: 1 to 4: 1 v/v) to give compound (+)-12a (2.21 g, 4.94 mmol) in 92 % yield. [alpha]22D +30.57 (c 0.57, CHCl3).
  • 9
  • [ 124-63-0 ]
  • [ 163226-45-7 ]
  • [ 925672-01-1 ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine; In dichloromethane; at 0℃; for 1h; On the basis of the Mitsunobu reaction of 5 with 7 or 15a-b, the condensation reaction of 5 with imidazol derivative (19) or a protected 3-deazaguanine (23) was initially investigated with the Mitsunobu reaction in order to synthesize carbocyclic 3-deazaguanosine (4). The coupling reaction of 5 with 19, which was prepared from 18 by following the previously reported method,16 provided N7-isomer (20) in 91% yield using the condition OfPh3P and DIAD in THF. The precursor 20 was subsequently converted to carbocyclic N7-3- deazaguanosine (21) in 56% yield (2 steps) by using methamolic ammonia and hydrogen chloride. The structure of 21 was determined by H- and C-NMR, as well as UV data (lambdamax 261 and 317 nm, pH 7.0), which was compared with previously reported data for N7-3- deazaguanosine (3).16b Furthermore, the Mitsunobu reaction of 5 with a protected 3- deazaguanine (23), which was synthesized from 19 by using cyclization with ammonia in a steel bomb and protection with isobutanoic anhydride, afforded a mixture of N9/N7-isomer (ratio 1 : 1) in 20% yield along with several by-products. Therefore, we investigated a more efficient condensation reaction in order to enhance the amount of Ncrisomer and reaction yield. The hydroxy group of 5 was transformed to a methansufonyl (Ms) group with MsCl in 92% yield.10 The substitution reaction of 22 with 23 in the presence of NaH and DMF solution gave Ncrisomer (24) in 40% yield along with 5% of N7-isomer (25), which could easily be removed from 24 by using silica gel column chromatography. The structure of 24 was determined with 1-D NOE and 1H- and 13C-NMR, as well as UV data ((lambdamax 271 and 300 nm, pH 7.0). AU data was consistent with 3-deazaguanosin (3) from previously reported literatures.1613 The significant interaction between the C1 '-H and aromatic C3-H of 24 was observed in NOE experiment as shown in figure 2. Subsequently, the compound 24 was treated with methalolic ammonia, followed by aqueous 0.1 M HCl solution to afford carbocyclic 3-deazaguanosine (C-3-DG, 4) in an 11% yield from imidazole derivative (19). In the case of the synthesis of C-3-DG (4), this simple substitution reaction was a more convenient strategy than the Mitsunobu reaction both by regioselectivity (Ng) and overall yield.
  • 10
  • [ 163226-45-7 ]
  • (3aS,4R,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol [ No CAS ]
  • 11
  • [ 163226-45-7 ]
  • [ 4928-88-5 ]
  • [ 878479-16-4 ]
  • 12
  • [ 163226-45-7 ]
  • [ 309947-86-2 ]
  • (1R,4R,5S)-9-N-[3-(trityloxymethyl)-4,5-O,O-isopropylidene-2-cyclopenten-L-yl]N6,N6-bis-(tert-butoxycarbonyl)adenine [ No CAS ]
  • 13
  • [ 163226-45-7 ]
  • 5-[(1S,2R,3R)-2,3-dihydroxy-4-hydroxymethyl-4-cyclopenten-1-yl]uracil [ No CAS ]
  • 14
  • [ 163226-45-7 ]
  • [ 925672-11-3 ]
  • 15
  • [ 163226-45-7 ]
  • 2-(2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3a<i>H</i>-cyclopenta[1,3]dioxol-4-yl)-3-hydroxy-propionitrile [ No CAS ]
  • 16
  • [ 163226-45-7 ]
  • [ 925672-02-2 ]
  • 17
  • [ 163226-45-7 ]
  • [ 925672-13-5 ]
  • 18
  • [ 163226-45-7 ]
  • 3-(cyanomethyl-amino)-2-(2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3a<i>H</i>-cyclopenta[1,3]dioxol-4-yl)-acrylonitrile [ No CAS ]
  • 19
  • [ 163226-45-7 ]
  • [ 925672-14-6 ]
  • 20
  • [ 163226-45-7 ]
  • [ 925672-10-2 ]
  • 21
  • [ 163226-45-7 ]
  • [ 925672-12-4 ]
  • 22
  • [ 163226-45-7 ]
  • 5-[(1S,2R,3R)-2,3-dihydroxy-4-hydroxymethyl-4-cyclopenten-1-yl]isocytosine hydrochloride [ No CAS ]
  • 23
  • [ 163226-45-7 ]
  • [2-cyano-2-(2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3a<i>H</i>-cyclopenta[1,3]dioxol-4-yl)-vinylamino]-acetic acid ethyl ester [ No CAS ]
  • 24
  • [ 163226-45-7 ]
  • ethyl 2,2-bis[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]-2-cyanoacetate [ No CAS ]
  • 25
  • [ 163226-45-7 ]
  • neplanocin A [ No CAS ]
  • 26
  • [ 934816-38-3 ]
  • [ 163226-45-7 ]
  • 27
  • [ 934816-31-6 ]
  • [ 163226-45-7 ]
  • 28
  • [ 934816-30-5 ]
  • [ 163226-45-7 ]
  • 29
  • [ 934816-35-0 ]
  • [ 163226-45-7 ]
  • 30
  • [ 934816-36-1 ]
  • [ 163226-45-7 ]
  • 31
  • [ 934816-32-7 ]
  • [ 163226-45-7 ]
  • 32
  • [ 934816-37-2 ]
  • [ 163226-45-7 ]
  • 34
  • [ 54187-70-1 ]
  • [ 163226-45-7 ]
  • 35
  • [ 96690-02-7 ]
  • [ 163226-45-7 ]
  • 36
  • [ 163226-45-7 ]
  • 1-(4,5-dihydroxy-3-hydroxymethylcyclopenten-2-enyl)-1H-1,2,3-triazole-4-carboxylic acid amide [ No CAS ]
  • 37
  • [ 163226-45-7 ]
  • 1-(4,5-dihydroxy-3-hydroxymethylcyclopent-2-enyl)-1H-1,2,4-triazole-3-carboxylic acid amide [ No CAS ]
 

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