Some partially benzylated pentose derivatives

Tejima, Setsuzo; Ness, Robert K.; Kaufman, R.L.; Fletcher, Hewitt G.

doi:10.1016/s0008-6215(00)82970-5

Cited by 32 publications

(8 citation statements)

References 9 publications

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“…2,3,4-Tri-O-benzyl-D-ribopyranose (disinthesis menurut prosedur (Tejima, 1968)), propanethiol, triphenyl phosphine (Aldrich), metil iodida, n-butyllithium (solution 15% in n-hexane, Sigma Aldrich/Merck-Schuchardt), 2,3,4-Tri-Obenzyl-D-xylopyranose (disinthesis menurut prosedur (Tejima, 1968) …”

Section: Alat Dan Bahanmentioning

confidence: 99%

Optimization of Reactions Opening Cyclic Ring of Pentose Sugar Derivatives through Dithioacetalisation Reactions

Nuriman

2017

J. I. Dasar

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Ring-opening reaction of cyclic pentose sugar derivatives of 2,3,4-Tri-O-benzyl-D-xylopyranose to derivatives of acyclic 2,3,4-Tri-O-benzyl-D-xylose-Dipropyl dithioacetal been done and optimized. The reaction was performed using a precursor propanathiol with concentrated HCl. Optimization of reaction conditions was conducted by varying propanathiol concentration, reaction time and optimization of the reaction temperature which the product ioslation conducted using a variety of solvents. The results of this reaction was obtained 2,3,4-Tri-O-benzyl-D-xylose-Dipropyl dithioacetal with the highest randemen (97%), better than the previous reaction through propanathiol excessive concentration, reaction time of 2 hours and the temperature of the reaction at room temperature. Product Isolations using solvent dikloromathane more effective than the use of other organic solvents. Purification of reaction products is done through a column chromatography using a solvent mixture of 20% ethyl acetate-hexane.

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Section: Alat Dan Bahanmentioning

confidence: 99%

Optimization of Reactions Opening Cyclic Ring of Pentose Sugar Derivatives through Dithioacetalisation Reactions

Nuriman

2017

J. I. Dasar

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“…xylopyranose. 1,2 The crude mixture of xylosides from the previous step was heated under reflux for 10 h with 1 M H 2 SO 4 (210 mL) -AcOH (240 mL) -dioxane (220 mL). After allowing the mixture to cool to rt, hexane (100 mL) and water (800 mL) were added with intense stirring.…”

Section: 34-tri-o-benzyl-d-mentioning

confidence: 99%

“…95%; R f 0.54 (25% EtOAc/hexanes);1 H NMR (CDCl 3 ): δ 7.41-7.36 (m, 15H), 7.09 (d, J = 8.5 Hz, 2H), 6.83 (d, J = 8.5 Hz, 2H), 5.95 (m, 1H), 5.39 (br d, J = 9.5 Hz, 1H), 5.34 (br d, J = 17.9 Hz, 1H), 4.85 (d, J = 11.6 Hz, 1H), 4.83 (d, J = 11.3 Hz, 1H), 4.68 (d, J = 11.8 Hz, 1H), 4.61 (d, J = 11.6 Hz, 1H), 4.54 (d, J = 11.3 Hz, 1H), 4.39 (d, J = 11.8 Hz, 1H), 4.06 (ψt, J = 6.1 Hz, 1H), 3.93 (dd, J = 7.4, 5.2 Hz, 1H), 3.82 (s, 3H), 3.68 (m, 1H), 3.51 (s, 3H), 3.49 (m, 1H), 3.00 (dd, J = 15.4, 4.4 Hz, 1H), 2.75 (dd, J = 15.4, 10.5 Hz, 1H); 13 C NMR (CDCl 3 ): δ 173.2, 158.5, 139.1, 139.0, 138.4, 135.6, 133.7, 129.4, 128.5, 128.4, 128.2, 127.9, 127.8, 127.7, 127.5, 119.1, 114.0, 82.4, 81.6, 75.0, 73.2, 70.8, 55.3, 51.5, 42.8, 36.9; HRMS m/z (EI) calcd for C 37 H 41 O 6 (M+H) + 581.2903, found 581.2910. 95%; 1 H NMR (CDCl 3 ): δ 7.38-7.33 (m, 15H), 6.70 (d, J = 8.0 Hz, 1H), 6.64 (br s, 1H), 6.59 (br d, J = 8.0 Hz, 1H), 5.93 (s, 2H), 5.92 (m, 1H), 5.38 (br d, J = 5.2 Hz, 1H), 5.34 (br d, J = 13.7 Hz, 1H), 4.83 (d, J = 11.8 Hz, 1H), 4.78 (d, J = 11.3 Hz, 1H), 4.65 (d, J = 11.6 Hz, 1H), 4.59 (d, J = 11.6 Hz, 1H), 4.50 (d, J = 11.3 Hz, 1H), 4.37 (d, J = 11.8 Hz, 1H), 4.07 (ψt, J = 6.1 Hz, 1H), 3.86 (dd, J = 6.9, 5.2 Hz, 1H), 3.60 (m, 1H), 3.51 (s, 3H), 3.47 (ψt, J = 5.2 Hz, 1H), 2.93 (dd, J = 15.7, 4.4 Hz, 1H), 2.69 (dd, J = 15.7, 10.5 Hz, 1H); 13 C NMR (CDCl 3 ): δ 173.0, 147.7, 146.…”

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confidence: 99%

An Approach to Pancratistatins via Ring‐Closing Metathesis: Efficient Synthesis of Novel 1‐Aryl‐1‐deoxyconduritols F.

Nadein

Kornienko

2004

ChemInform

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An Approach to Pancratistatins via Ring-Closing Metathesis: Efficient Synthesis of Novel 1-Aryl-1-deoxyconduritols F. -An efficient synthetic route to title compounds [cf. (VI)-(VIII)] from (I) is developed. A range of aromatic residues is incorporated in the cyclitol skeleton with total stereochemical control utilizing a diastereoselective aryl cuprate addition to a γ-alkoxy enoate. The multi-step sequence is optimized for the production of gram quantities of these compounds. - (NADEIN, O. N.; KORNIENKO*, A.; Org. Lett. 6 (2004) 5, 831-834; Dep. Chem., N. Mex. Inst. Min. Technol., Socorro, NM 87801, USA; Eng.) -Steudel 27-175

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“…The latter is lysis of 21 employing allylamine in methanol afforded amide 22, which was subsequently oxidised by using pyridi-easily accessible from xylose in a known [30] three-step procedure. Accordingly, hydrogenation of 20, followed by diol protection, afforded lactone 21 in excellent yield.…”

Section: Quinolizidine Systemsmentioning

confidence: 99%

Synthesis Mediated by Ring-Closing Metathesis – Applications in the Synthesis of Azasugars and Alkaloids

Pandit¹,

Overkleeft²,

Borer³

et al. 1999

Eur. J. Org. Chem.

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The application of the ring-closing metathesis (RCM) castanospermine (5) is presented. The utilisation of two RCM steps in the synthetic sequence leading to the multicyclic reaction to the construction of a wide variety of nitrogencontaining ring systems is described. The examples include ABCDE nucleus 7 of the complex alkaloid manzamine A (6) is discussed. pyrrolizidine, indolizidine, and quinolizidine derivatives related to azasugars. A formal total synthesis of

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Some partially benzylated pentose derivatives

Cited by 32 publications

References 9 publications

Optimization of Reactions Opening Cyclic Ring of Pentose Sugar Derivatives through Dithioacetalisation Reactions

Optimization of Reactions Opening Cyclic Ring of Pentose Sugar Derivatives through Dithioacetalisation Reactions

An Approach to Pancratistatins via Ring‐Closing Metathesis: Efficient Synthesis of Novel 1‐Aryl‐1‐deoxyconduritols F.

Synthesis Mediated by Ring-Closing Metathesis – Applications in the Synthesis of Azasugars and Alkaloids

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