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[ CAS No. 7735-43-5 ] {[proInfo.proName]}

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Quality Control of [ 7735-43-5 ]

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Product Details of [ 7735-43-5 ]

CAS No. :7735-43-5 MDL No. :MFCD01076309
Formula : C20H42O2 Boiling Point : -
Linear Structure Formula :- InChI Key :PGMMMHFNKZSYEP-UHFFFAOYSA-N
M.W : 314.55 Pubchem ID :4134690
Synonyms :

Calculated chemistry of [ 7735-43-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 19
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 100.58
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -2.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.93
Log Po/w (XLOGP3) : 7.69
Log Po/w (WLOGP) : 5.99
Log Po/w (MLOGP) : 4.47
Log Po/w (SILICOS-IT) : 6.86
Consensus Log Po/w : 5.99

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.38
Solubility : 0.00131 mg/ml ; 0.00000416 mol/l
Class : Moderately soluble
Log S (Ali) : -8.38
Solubility : 0.00000131 mg/ml ; 0.0000000042 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -6.81
Solubility : 0.0000489 mg/ml ; 0.000000156 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.79

Safety of [ 7735-43-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7735-43-5 ]

* 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 [ 7735-43-5 ]

[ 7735-43-5 ] Synthesis Path-Downstream   1~100

  • 1
  • [ 7735-43-5 ]
  • [ 24772-69-8 ]
YieldReaction ConditionsOperation in experiment
With phosphorus; iodine at 180℃;
  • 3
  • [ 3669-80-5 ]
  • [ 7735-43-5 ]
YieldReaction ConditionsOperation in experiment
With sodium In methanol (electrolysis);
  • 5
  • [ 7735-43-5 ]
  • [ 115314-14-2 ]
  • 1,1'-Di-O-eicosamethylenedi-sn-glycerol 3,3'-bis(3'-nitrobenzenesulfonate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% In chloroform for 48h; Heating;
  • 6
  • [ 7735-43-5 ]
  • [ 115314-14-2 ]
  • [ 157999-16-1 ]
  • 7
  • [ 7735-43-5 ]
  • [ 14296-16-3 ]
  • [ 92002-48-7 ]
YieldReaction ConditionsOperation in experiment
49% With hydrogen bromide In Petroleum ether for 24h; Heating;
  • 9
  • [ 2424-92-2 ]
  • [ 7735-43-5 ]
YieldReaction ConditionsOperation in experiment
51% With lithium aluminium tetrahydride; In tetrahydrofuran;Inert atmosphere; Reflux; Under an atmosphere of nitrogen, <strong>[2424-92-2]eicosanedioic acid</strong> (890 mg, 2.60 mmol, 1 equiv) was dissolved in freshly distilled THF (60 mL). The solution was cooled to 0 C and to this was added in small portions lithium aluminum hydride (370 mg, 9.75 mmol, 3.75 equiv). The mixture was warmed to rt and then heated at reflux temperature for 12 h. The mixture was cooled to 0 C, quenched with wet THF and then water (5 mL), stirred at rt for 1 h, then concentrated and dried under high vacuum. The remaining residue was extracted with boiling methanol, then boiling ethyl acetate, and the combined organic extracts were filtered, and the filtrate concentrated. High-vacuum drying gave a white solid that was washed with a solution of 1% w/w sodium carbonate in water (100 mL). The solid was collected by filtration and washed with water (100 mL). High-vacuum drying gave the product (416 mg, 1.32 mmol, 51%) as a white solid; mp >260 C; 1H NMR (400 MHz, CD3OD): delta 1.18-1.38 (m, 32H), 1.46-1.57 (m, 4H), 3.54 (t, J = 6.6 Hz, 4H); 13C NMR (100 MHz, DMSO-d6 + CDCl3): delta 25.4, 28.8, 28.9 (5C), 29.0, 32.4, 60.9.
  • 10
  • [ 84845-63-6 ]
  • [ 7735-43-5 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In methanol Heating;
  • 11
  • [ 3669-80-5 ]
  • [ 112-30-1 ]
  • [ 13019-22-2 ]
  • [ 7735-43-5 ]
YieldReaction ConditionsOperation in experiment
42% With potassium methanolate In methanol at 40℃; electrolysis: anode: platinum foil; current source: galvanostat; current density 200 mA cm-2; current consumption: 3.03 F mol-1; cell voltage 50-60 V; Yield given;
42% With potassium methanolate In methanol at 40℃; electrolysis: anode: platinum foil; current source: galvanostat; current density 200 mA cm-2; current consumption: 3.03 F mol-1; cell voltage 50-60 V; Yields of byproduct given;
  • 12
  • [ 2930-05-4 ]
  • [ 7735-43-5 ]
  • [ 214753-38-5 ]
YieldReaction ConditionsOperation in experiment
80% With trifluorormethanesulfonic acid In chloroform for 48h; Heating;
  • 13
  • [ 7735-43-5 ]
  • [ 92002-18-1 ]
  • C80H90O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With pyridine; dmap; dicyclohexyl-carbodiimide at 0 - 20℃; for 3h;
  • 14
  • [ 7735-43-5 ]
  • [ 92002-19-2 ]
  • C126H126O18 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With pyridine; dmap; dicyclohexyl-carbodiimide at 0 - 20℃; for 3h;
  • 15
  • octane-dicarboxylic acid-(1.18)-dimethyl ester [ No CAS ]
  • [ 7735-43-5 ]
  • [ 62643-46-3 ]
  • 16
  • [ 42235-38-1 ]
  • [ 7735-43-5 ]
YieldReaction ConditionsOperation in experiment
100% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 15h;
99% With lithium aluminium tetrahydride In tetrahydrofuran for 0.5h; Reflux; Inert atmosphere;
62.5% With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran for 3h;
59% With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice;
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In diethyl ether at 40℃; for 72h;
With lithium aluminium tetrahydride In tetrahydrofuran

  • 17
  • [ 7735-43-5 ]
  • [ 76-83-5 ]
  • [ 745073-19-2 ]
YieldReaction ConditionsOperation in experiment
With pyridine In N,N-dimethyl-formamide at 20℃; for 1h;
  • 18
  • [ 7735-43-5 ]
  • [ 1663-67-8 ]
  • 1,5-Dioxa-cyclopentacosane-2,4-dione [ No CAS ]
  • cyco[2]eicosylenemalonate [ No CAS ]
  • C69H126O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 5% 2: 16% 3: 3% With pyridine In dichloromethane at 20℃; for 56h;
  • 19
  • [ 7735-43-5 ]
  • [ 838888-27-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 79.7 percent / aq. HBr; Ac2O / 5 h / Heating 2: 44 percent / Na2CO3; KI / various solvent(s) / 3 h / Heating
  • 20
  • [ 7735-43-5 ]
  • 1-hydroxymethyl-3,26-dioxabicyclo[22.2.1]heptaeicos-23(E)-ene-4,25-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: pyridine / dimethylformamide / 1 h / 20 °C 2.1: pyridinium chloroformate; molecular sieves 4A / CH2Cl2 / 1 h / 20 °C 3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C 3.2: tetrahydrofuran / 2 h / -78 °C 4.1: Et3N; MeSO2Cl / CH2Cl2 / 2.5 h / 0 - 20 °C 4.2: diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 0.5 h / 0 °C 5.1: HCO2H / diethyl ether / 1 h / 20 °C 6.1: pyridinium dichromate / dimethylformamide / 24 h / 20 °C 7.1: aq. ammonium cerium nitrate / acetonitrile / 0.5 h / 0 °C 8.1: 4-(dimethylamino)pyridine; 4-(dimethylamino)pyridine hydrochloride; dicyclohexylcarbodiimide / CH2Cl2 / 16 h / Heating 9.1: BCl3 / CH2Cl2 / 2 h / -78 °C
  • 21
  • [ 7735-43-5 ]
  • (Z)-1-Hydroxymethyl-3,26-dioxa-bicyclo[22.2.1]heptacos-23-ene-4,25-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: pyridine / dimethylformamide / 1 h / 20 °C 2.1: pyridinium chloroformate; molecular sieves 4A / CH2Cl2 / 1 h / 20 °C 3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C 3.2: tetrahydrofuran / 2 h / -78 °C 4.1: Et3N; MeSO2Cl / CH2Cl2 / 2.5 h / 0 - 20 °C 4.2: diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 0.5 h / 0 °C 5.1: HCO2H / diethyl ether / 1 h / 20 °C 6.1: pyridinium dichromate / dimethylformamide / 24 h / 20 °C 7.1: aq. ammonium cerium nitrate / acetonitrile / 0.5 h / 0 °C 8.1: 4-(dimethylamino)pyridine; 4-(dimethylamino)pyridine hydrochloride; dicyclohexylcarbodiimide / CH2Cl2 / 16 h / Heating 9.1: BCl3 / CH2Cl2 / 2 h / -78 °C
  • 22
  • [ 7735-43-5 ]
  • [ 745073-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / dimethylformamide / 1 h / 20 °C 2: pyridinium chloroformate; molecular sieves 4A / CH2Cl2 / 1 h / 20 °C
  • 23
  • [ 7735-43-5 ]
  • [ 745073-55-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: pyridine / dimethylformamide / 1 h / 20 °C 2.1: pyridinium chloroformate; molecular sieves 4A / CH2Cl2 / 1 h / 20 °C 3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C 3.2: tetrahydrofuran / 2 h / -78 °C 4.1: Et3N; MeSO2Cl / CH2Cl2 / 2.5 h / 0 - 20 °C 4.2: diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 0.5 h / 0 °C 5.1: HCO2H / diethyl ether / 1 h / 20 °C 6.1: pyridinium dichromate / dimethylformamide / 24 h / 20 °C 7.1: aq. ammonium cerium nitrate / acetonitrile / 0.5 h / 0 °C 8.1: 4-(dimethylamino)pyridine; 4-(dimethylamino)pyridine hydrochloride; dicyclohexylcarbodiimide / CH2Cl2 / 16 h / Heating
  • 24
  • [ 7735-43-5 ]
  • [ 745073-56-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: pyridine / dimethylformamide / 1 h / 20 °C 2.1: pyridinium chloroformate; molecular sieves 4A / CH2Cl2 / 1 h / 20 °C 3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C 3.2: tetrahydrofuran / 2 h / -78 °C 4.1: Et3N; MeSO2Cl / CH2Cl2 / 2.5 h / 0 - 20 °C 4.2: diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 0.5 h / 0 °C 5.1: HCO2H / diethyl ether / 1 h / 20 °C 6.1: pyridinium dichromate / dimethylformamide / 24 h / 20 °C 7.1: aq. ammonium cerium nitrate / acetonitrile / 0.5 h / 0 °C 8.1: 4-(dimethylamino)pyridine; 4-(dimethylamino)pyridine hydrochloride; dicyclohexylcarbodiimide / CH2Cl2 / 16 h / Heating
  • 25
  • [ 7735-43-5 ]
  • [ 745073-48-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: pyridine / dimethylformamide / 1 h / 20 °C 2.1: pyridinium chloroformate; molecular sieves 4A / CH2Cl2 / 1 h / 20 °C 3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C 3.2: tetrahydrofuran / 2 h / -78 °C 4.1: Et3N; MeSO2Cl / CH2Cl2 / 2.5 h / 0 - 20 °C 4.2: diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 0.5 h / 0 °C 5.1: HCO2H / diethyl ether / 1 h / 20 °C 6.1: pyridinium dichromate / dimethylformamide / 24 h / 20 °C 7.1: aq. ammonium cerium nitrate / acetonitrile / 0.5 h / 0 °C
  • 26
  • [ 7735-43-5 ]
  • [ 745073-49-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: pyridine / dimethylformamide / 1 h / 20 °C 2.1: pyridinium chloroformate; molecular sieves 4A / CH2Cl2 / 1 h / 20 °C 3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C 3.2: tetrahydrofuran / 2 h / -78 °C 4.1: Et3N; MeSO2Cl / CH2Cl2 / 2.5 h / 0 - 20 °C 4.2: diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 0.5 h / 0 °C 5.1: HCO2H / diethyl ether / 1 h / 20 °C 6.1: pyridinium dichromate / dimethylformamide / 24 h / 20 °C 7.1: aq. ammonium cerium nitrate / acetonitrile / 0.5 h / 0 °C
  • 27
  • [ 7735-43-5 ]
  • [ 745073-34-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: pyridine / dimethylformamide / 1 h / 20 °C 2.1: pyridinium chloroformate; molecular sieves 4A / CH2Cl2 / 1 h / 20 °C 3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C 3.2: tetrahydrofuran / 2 h / -78 °C 4.1: Et3N; MeSO2Cl / CH2Cl2 / 2.5 h / 0 - 20 °C 4.2: diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 0.5 h / 0 °C 5.1: HCO2H / diethyl ether / 1 h / 20 °C
  • 28
  • [ 7735-43-5 ]
  • [ 745073-35-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: pyridine / dimethylformamide / 1 h / 20 °C 2.1: pyridinium chloroformate; molecular sieves 4A / CH2Cl2 / 1 h / 20 °C 3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C 3.2: tetrahydrofuran / 2 h / -78 °C 4.1: Et3N; MeSO2Cl / CH2Cl2 / 2.5 h / 0 - 20 °C 4.2: diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 0.5 h / 0 °C 5.1: HCO2H / diethyl ether / 1 h / 20 °C
  • 29
  • [ 7735-43-5 ]
  • [ 745073-41-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: pyridine / dimethylformamide / 1 h / 20 °C 2.1: pyridinium chloroformate; molecular sieves 4A / CH2Cl2 / 1 h / 20 °C 3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C 3.2: tetrahydrofuran / 2 h / -78 °C 4.1: Et3N; MeSO2Cl / CH2Cl2 / 2.5 h / 0 - 20 °C 4.2: diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 0.5 h / 0 °C 5.1: HCO2H / diethyl ether / 1 h / 20 °C 6.1: pyridinium dichromate / dimethylformamide / 24 h / 20 °C
  • 30
  • [ 7735-43-5 ]
  • [ 745073-42-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: pyridine / dimethylformamide / 1 h / 20 °C 2.1: pyridinium chloroformate; molecular sieves 4A / CH2Cl2 / 1 h / 20 °C 3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C 3.2: tetrahydrofuran / 2 h / -78 °C 4.1: Et3N; MeSO2Cl / CH2Cl2 / 2.5 h / 0 - 20 °C 4.2: diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 0.5 h / 0 °C 5.1: HCO2H / diethyl ether / 1 h / 20 °C 6.1: pyridinium dichromate / dimethylformamide / 24 h / 20 °C
  • 31
  • [ 7735-43-5 ]
  • 5-benzyloxymethyl-3-(1-hydroxy-20-trityloxy-eicosyl)-5-(4-methoxy-phenoxymethyl)-dihydro-furan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: pyridine / dimethylformamide / 1 h / 20 °C 2.1: pyridinium chloroformate; molecular sieves 4A / CH2Cl2 / 1 h / 20 °C 3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C 3.2: tetrahydrofuran / 2 h / -78 °C
  • 32
  • [ 7735-43-5 ]
  • [ 745073-28-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: pyridine / dimethylformamide / 1 h / 20 °C 2.1: pyridinium chloroformate; molecular sieves 4A / CH2Cl2 / 1 h / 20 °C 3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C 3.2: tetrahydrofuran / 2 h / -78 °C 4.1: Et3N; MeSO2Cl / CH2Cl2 / 2.5 h / 0 - 20 °C 4.2: diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 0.5 h / 0 °C
  • 33
  • [ 7735-43-5 ]
  • [ 745073-27-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: pyridine / dimethylformamide / 1 h / 20 °C 2.1: pyridinium chloroformate; molecular sieves 4A / CH2Cl2 / 1 h / 20 °C 3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C 3.2: tetrahydrofuran / 2 h / -78 °C 4.1: Et3N; MeSO2Cl / CH2Cl2 / 2.5 h / 0 - 20 °C 4.2: diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 0.5 h / 0 °C
  • 34
  • [ 7735-43-5 ]
  • C30H66N2O8P2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) Et3N, 2.) H2O / 1.) ether, THF, room temperature, 4 h, 2.) overnight 2: 85 percent / tetrahydrofuran / 16 h / 50 °C
  • 35
  • [ 111-81-9 ]
  • [ 7735-43-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydroboration-oxidation 2: 42 percent / 1M potassium methoxide / methanol / 40 °C / electrolysis: anode: platinum foil; current source: galvanostat; current density 200 mA cm-2; current consumption: 3.03 F mol-1; cell voltage 50-60 V
Stage #1: Methyl 10-undecenoate With Grubbs catalyst first generation at 50℃; for 3h; Inert atmosphere; Stage #2: With potassium <i>tert</i>-butylate; hydrogen; (2-aminoethyl)diphenylphosphane In tetrahydrofuran at 70℃; for 16h; Inert atmosphere; chemoselective reaction;
Multi-step reaction with 3 steps 1: Grubbs catalyst first generation / 3 h / 20 - 50 °C 2: 20% palladium hydroxide-activated charcoal; hydrogen / methanol; ethyl acetate / 1 h / 20 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / Reflux; Inert atmosphere
  • 36
  • [ 3903-40-0 ]
  • [ 7735-43-5 ]
  • 37
  • [ 1731-79-9 ]
  • [ 7735-43-5 ]
  • 38
  • [ 7735-43-5 ]
  • [ 122892-08-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 65 percent / CF3SO3H / CHCl3 / 48 h / Heating 2: 84 percent / Proton Sponge / CHCl3 / 48 h / Heating 3: dimethylsulfoxide; dimethylformamide / 16 h / 60 °C 4: LAH / tetrahydrofuran / 16 h / 67 °C
  • 39
  • [ 7735-43-5 ]
  • Acetic acid (R)-3-[20-((R)-3-acetoxy-2-decyloxy-propoxy)-icosyloxy]-2-decyloxy-propyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 65 percent / CF3SO3H / CHCl3 / 48 h / Heating 2: 84 percent / Proton Sponge / CHCl3 / 48 h / Heating 3: dimethylsulfoxide; dimethylformamide / 16 h / 60 °C
  • 40
  • [ 7735-43-5 ]
  • 2,2'-Di-O-decyl-3,3'-di-O-eicosamethylenebis(sn-glycero-1-phosphocholine) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 65 percent / CF3SO3H / CHCl3 / 48 h / Heating 2: 84 percent / Proton Sponge / CHCl3 / 48 h / Heating 3: dimethylsulfoxide; dimethylformamide / 16 h / 60 °C 4: LAH / tetrahydrofuran / 16 h / 67 °C 5: 1.) Et3N / 1.) benzene, room temp., 36 h, 2.) CH3CN, 65 deg C, 48 h
  • 41
  • [ 7735-43-5 ]
  • 2-O-Eicosyl-3,3'-di-O-eicosamethylenedi-sn-glycerol 1,1'-bis(3'-nitrobenzenesulfonate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 65 percent / CF3SO3H / CHCl3 / 48 h / Heating 2: 63 percent / Proton Sponge / CHCl3 / 48 h / Heating
  • 42
  • [ 7735-43-5 ]
  • [ 157999-19-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 65 percent / CF3SO3H / CHCl3 / 48 h / Heating 2: 84 percent / Proton Sponge / CHCl3 / 48 h / Heating
  • 43
  • [ 7735-43-5 ]
  • 2,2'-Di-O-decyl-1,1'-di-O-eicosamethylenedi-sn-glycerol 3,3'-bis(3'-nitrobenzenesulfonate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 66 percent / CF3SO3H / CHCl3 / 48 h / Heating 2: 83 percent / Proton Sponge / CHCl3 / 48 h / Heating
  • 44
  • [ 7735-43-5 ]
  • [ 149340-92-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Br2 / petroleum ether 2: 50 percent / ethanol / Heating 3: hydrazine / ethanol
  • 45
  • [ 7735-43-5 ]
  • Thiobenzoic acid S-(20-hydroxy-icosyl) ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Br2 / petroleum ether 2: 50 percent / ethanol / Heating
  • 46
  • [ 53463-68-6 ]
  • [ 7735-43-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 27.4 g / toluene-p-sulphonic acid / diethyl ether / 17 h / 20 °C
  • 47
  • [ 7735-43-5 ]
  • [ 128368-83-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 67 percent / BH3-Me2S / tetrahydrofuran / 20 h / Ambient temperature 5: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h / Ambient temperature 6: 95 percent / PPTS / ethanol / 1 h / Heating
Multi-step reaction with 4 steps 2: 67 percent / BH3-THF / from 0 deg C to RT, 20 h 3: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h 4: 95 percent / pyridinium toluene-p-sulphonate / ethanol / 1 h / Heating
  • 48
  • [ 7735-43-5 ]
  • [ 134171-72-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 67 percent / BH3-Me2S / tetrahydrofuran / 20 h / Ambient temperature 5: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h / Ambient temperature 6: 95 percent / PPTS / ethanol / 1 h / Heating 7: 87 percent / Jones reagent / acetone 8: 78 percent / diethyl ether; tetrahydrofuran / 0 °C 9: 69 percent / K2CO3 / methanol; tetrahydrofuran / 0.75 h / Ambient temperature
Multi-step reaction with 7 steps 2: 67 percent / BH3-THF / from 0 deg C to RT, 20 h 3: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h 4: 95 percent / pyridinium toluene-p-sulphonate / ethanol / 1 h / Heating 5: 89 percent / CrO3, H2SO4 / acetone 6: 78 percent / diethyl ether 7: 69 percent / K2CO3, MeOH / tetrahydrofuran / 0.75 h
  • 49
  • [ 7735-43-5 ]
  • [ 128368-80-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 67 percent / BH3-Me2S / tetrahydrofuran / 20 h / Ambient temperature 5: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h / Ambient temperature 6: 95 percent / PPTS / ethanol / 1 h / Heating 7: 87 percent / Jones reagent / acetone 8: 78 percent / diethyl ether; tetrahydrofuran / 0 °C 9: 69 percent / K2CO3 / methanol; tetrahydrofuran / 0.75 h / Ambient temperature 10: 76 percent / CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature
Multi-step reaction with 8 steps 2: 67 percent / BH3-THF / from 0 deg C to RT, 20 h 3: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h 4: 95 percent / pyridinium toluene-p-sulphonate / ethanol / 1 h / Heating 5: 89 percent / CrO3, H2SO4 / acetone 6: 78 percent / diethyl ether 7: 69 percent / K2CO3, MeOH / tetrahydrofuran / 0.75 h 8: 76 percent / CrO3*2-pyridine / CH2Cl2
  • 50
  • [ 7735-43-5 ]
  • [ 128368-84-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 67 percent / BH3-Me2S / tetrahydrofuran / 20 h / Ambient temperature
Multi-step reaction with 2 steps 2: 67 percent / BH3-THF / from 0 deg C to RT, 20 h
  • 51
  • [ 7735-43-5 ]
  • [ 128368-86-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 67 percent / BH3-Me2S / tetrahydrofuran / 20 h / Ambient temperature 5: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h / Ambient temperature 6: 95 percent / PPTS / ethanol / 1 h / Heating 7: 87 percent / Jones reagent / acetone
Multi-step reaction with 5 steps 2: 67 percent / BH3-THF / from 0 deg C to RT, 20 h 3: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h 4: 95 percent / pyridinium toluene-p-sulphonate / ethanol / 1 h / Heating 5: 89 percent / CrO3, H2SO4 / acetone
  • 52
  • [ 7735-43-5 ]
  • [ 128368-82-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min
  • 53
  • [ 7735-43-5 ]
  • [ 128368-87-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 67 percent / BH3-Me2S / tetrahydrofuran / 20 h / Ambient temperature 5: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h / Ambient temperature 6: 95 percent / PPTS / ethanol / 1 h / Heating 7: 87 percent / Jones reagent / acetone 8: 78 percent / diethyl ether; tetrahydrofuran / 0 °C
Multi-step reaction with 6 steps 2: 67 percent / BH3-THF / from 0 deg C to RT, 20 h 3: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h 4: 95 percent / pyridinium toluene-p-sulphonate / ethanol / 1 h / Heating 5: 89 percent / CrO3, H2SO4 / acetone 6: 78 percent / diethyl ether
  • 54
  • [ 7735-43-5 ]
  • [ 128368-85-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 67 percent / BH3-Me2S / tetrahydrofuran / 20 h / Ambient temperature 5: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h / Ambient temperature
Multi-step reaction with 3 steps 2: 67 percent / BH3-THF / from 0 deg C to RT, 20 h 3: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h
  • 55
  • [ 7735-43-5 ]
  • [ 128368-79-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 67 percent / BH3-Me2S / tetrahydrofuran / 20 h / Ambient temperature 5: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h / Ambient temperature 6: 95 percent / PPTS / ethanol / 1 h / Heating 7: 87 percent / Jones reagent / acetone 8: 78 percent / diethyl ether; tetrahydrofuran / 0 °C 9: 69 percent / K2CO3 / methanol; tetrahydrofuran / 0.75 h / Ambient temperature 10: 76 percent / CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature 11: 66 percent / NaOCH3 / tetrahydrofuran / 0.5 h / 0 °C 12: 82 percent / KOH / toluene; methanol / 20 h / Heating
Multi-step reaction with 10 steps 2: 67 percent / BH3-THF / from 0 deg C to RT, 20 h 3: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h 4: 95 percent / pyridinium toluene-p-sulphonate / ethanol / 1 h / Heating 5: 89 percent / CrO3, H2SO4 / acetone 6: 78 percent / diethyl ether 7: 69 percent / K2CO3, MeOH / tetrahydrofuran / 0.75 h 8: 76 percent / CrO3*2-pyridine / CH2Cl2 9: 66 percent / MeONa / tetrahydrofuran / 0.5 h 10: 78 percent / KOH, MeOH / toluene / 20 h / Heating
  • 56
  • [ 7735-43-5 ]
  • [ 128368-81-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 67 percent / BH3-Me2S / tetrahydrofuran / 20 h / Ambient temperature 5: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h / Ambient temperature 6: 95 percent / PPTS / ethanol / 1 h / Heating 7: 87 percent / Jones reagent / acetone 8: 78 percent / diethyl ether; tetrahydrofuran / 0 °C 9: 69 percent / K2CO3 / methanol; tetrahydrofuran / 0.75 h / Ambient temperature 10: 76 percent / CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature 11: 66 percent / NaOCH3 / tetrahydrofuran / 0.5 h / 0 °C
Multi-step reaction with 9 steps 2: 67 percent / BH3-THF / from 0 deg C to RT, 20 h 3: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h 4: 95 percent / pyridinium toluene-p-sulphonate / ethanol / 1 h / Heating 5: 89 percent / CrO3, H2SO4 / acetone 6: 78 percent / diethyl ether 7: 69 percent / K2CO3, MeOH / tetrahydrofuran / 0.75 h 8: 76 percent / CrO3*2-pyridine / CH2Cl2 9: 66 percent / MeONa / tetrahydrofuran / 0.5 h
  • 57
  • [ 7735-43-5 ]
  • [ 128368-78-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 67 percent / BH3-Me2S / tetrahydrofuran / 20 h / Ambient temperature 5: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h / Ambient temperature 6: 95 percent / PPTS / ethanol / 1 h / Heating 7: 87 percent / Jones reagent / acetone 8: 78 percent / diethyl ether; tetrahydrofuran / 0 °C 9: 69 percent / K2CO3 / methanol; tetrahydrofuran / 0.75 h / Ambient temperature 10: 76 percent / CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature 11: 66 percent / NaOCH3 / tetrahydrofuran / 0.5 h / 0 °C 12: 82 percent / KOH / toluene; methanol / 20 h / Heating 13: 1) 1,1'-thionyldiimidazole / 1) THF, 1 h, 2)CHCl3, 5 days, room temperature
Multi-step reaction with 12 steps 2: 67 percent / BH3-THF / from 0 deg C to RT, 20 h 3: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h 4: 95 percent / pyridinium toluene-p-sulphonate / ethanol / 1 h / Heating 5: 89 percent / CrO3, H2SO4 / acetone 6: 78 percent / diethyl ether 7: 69 percent / K2CO3, MeOH / tetrahydrofuran / 0.75 h 8: 76 percent / CrO3*2-pyridine / CH2Cl2 9: 66 percent / MeONa / tetrahydrofuran / 0.5 h 10: 78 percent / KOH, MeOH / toluene / 20 h / Heating 11: tetrahydrofuran 12: 8 percent / CHCl3 / 120 h / 50 °C
  • 58
  • [ 7735-43-5 ]
  • [ 92002-47-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature
  • 59
  • [ 7735-43-5 ]
  • [ 134171-69-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 89 percent / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C 5: 1) triphenylphosphine dibromide / 1) CH2Cl2, 30 min, 2) DMSO, reflux, 20 h 6: AlCl3, LiAH4 / tetrahydrofuran / 20 h / Ambient temperature 7: formic acid / H2O / 20 h / Heating
  • 60
  • [ 7735-43-5 ]
  • 4-(22-Amino-docosyl)-benzoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 89 percent / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C 5: 1) triphenylphosphine dibromide / 1) CH2Cl2, 30 min, 2) DMSO, reflux, 20 h 6: AlCl3, LiAH4 / tetrahydrofuran / 20 h / Ambient temperature
  • 61
  • [ 7735-43-5 ]
  • [ 134171-67-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 89 percent / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C 5: 1) triphenylphosphine dibromide / 1) CH2Cl2, 30 min, 2) DMSO, reflux, 20 h
  • 62
  • [ 7735-43-5 ]
  • [ 134171-70-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 89 percent / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C 5: 1) triphenylphosphine dibromide / 1) CH2Cl2, 30 min, 2) DMSO, reflux, 20 h 6: AlCl3, LiAH4 / tetrahydrofuran / 20 h / Ambient temperature 7: formic acid / H2O / 20 h / Heating 8: CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature
  • 63
  • [ 7735-43-5 ]
  • [ 134171-66-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 89 percent / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C
  • 64
  • [ 7735-43-5 ]
  • [ 134171-71-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 89 percent / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C 5: 1) triphenylphosphine dibromide / 1) CH2Cl2, 30 min, 2) DMSO, reflux, 20 h 6: AlCl3, LiAH4 / tetrahydrofuran / 20 h / Ambient temperature 7: formic acid / H2O / 20 h / Heating 8: CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature 9: 48 percent / NaOCH3 / tetrahydrofuran / 2 h / Ambient temperature
  • 65
  • [ 7735-43-5 ]
  • [ 134171-65-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating 2: PPTS / CH2Cl2 / 20 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min 4: 89 percent / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C 5: 1) triphenylphosphine dibromide / 1) CH2Cl2, 30 min, 2) DMSO, reflux, 20 h 6: AlCl3, LiAH4 / tetrahydrofuran / 20 h / Ambient temperature 7: formic acid / H2O / 20 h / Heating 8: CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature 9: 48 percent / NaOCH3 / tetrahydrofuran / 2 h / Ambient temperature 10: 86 percent / toluene; acetone / 3 h / 70 °C
  • 66
  • [ 7735-43-5 ]
  • 1-Imidazol-1-yl-21-[4-((1E,3E,5E)-6-phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 2: 67 percent / BH3-THF / from 0 deg C to RT, 20 h 3: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH2Cl2 / 20 h 4: 95 percent / pyridinium toluene-p-sulphonate / ethanol / 1 h / Heating 5: 89 percent / CrO3, H2SO4 / acetone 6: 78 percent / diethyl ether 7: 69 percent / K2CO3, MeOH / tetrahydrofuran / 0.75 h 8: 76 percent / CrO3*2-pyridine / CH2Cl2 9: 66 percent / MeONa / tetrahydrofuran / 0.5 h 10: 78 percent / KOH, MeOH / toluene / 20 h / Heating 11: tetrahydrofuran
  • 67
  • [ 1860-44-2 ]
  • [ 7735-43-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. NaOH / Heating 2: Na / methanol / (electrolysis)
  • 68
  • [ 7735-43-5 ]
  • [ 124-63-0 ]
  • [ 1043569-44-3 ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h; 4.5.2 1,20-Bis-(methanesulfonyloxy)eicosane Under an atmosphere of nitrogen, 1,20-eicosanediol (403 mg, 1.28 mmol, 1 equiv) was dissolved in warm THF (10 mL) and the solution was then cooled to rt. To this solution was added triethylamine (0.44 mL, 320 mg, 3.16 mmol, 2.5 equiv), the mixture cooled to 0 °C, and methanesulfonyl chloride (0.22 mL, 326 mg, 2.85 mmol, 2.2 equiv) was added. The mixture was stirred at rt for 2 h, methylene chloride (5 mL) added, and the mixture heated at reflux temperature for 1 min. The mixture was then stirred at rt overnight, concentrated and dried under high vacuum. The resulting white solid was washed with water (250 mL) and the solid collected by filtration. High-vacuum drying gave the product (533 mg, 1.13 mmol, 88%) as a white solid; mp 94-95 °C; 1H NMR (400 MHz, DMSO-d6): δ 1.10-1.40 (m, 32H), 1.57-1.71 (m, 4H), 3.15 (s, 6H), 4.17 (t, J = 6.2 Hz, 4H); 13C NMR (100 MHz, DMSO-d6): δ 24.6, 28.2, 28.3, 28.5, 28.6, 28.7 (4C), 36.5, 70.1; HRMS (ESI) [M+Na]+ Calcd for C22H46O6S2Na: 493.2634. Found: 493.2641.
45% With trimethylamine hydrochloride; triethylamine In dichloromethane at 0℃; for 0.166667h;
  • 69
  • [ 7735-43-5 ]
  • [ 4801-15-4 ]
  • C35H54O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride
Stage #1: 1,20-eicosanediol With sodium hydride In tetrahydrofuran Inert atmosphere; Stage #2: 3-bromo-1,1-diphenyl-1-propene In tetrahydrofuran Inert atmosphere; Reflux;
  • 70
  • [ 7735-43-5 ]
  • [ 58479-61-1 ]
  • [ 1192540-89-8 ]
YieldReaction ConditionsOperation in experiment
57% With 1H-imidazole In N,N-dimethyl-formamide
44% With pyridine at 80℃; for 24h; (20-((tert-Butyldiphenylsilyl)oxy)eicosan-1-ol (11) A solution of eicosan-1,20-diol(12.2 g, 38.8 mmol) in pyridine (97 mL) was treated with TBDPSCl (1.10 mL, 42.7 mmol)and stirred for 24 h at 80 C. H2O (150 mL) was added and the aqueous phase was extractedwith CH2Cl2 (3 150 mL). The combined organic phases were dried over Na2SO4 andconcentrated in vacuo. The residue was dissolved in toluene (3 100 mL) and concentratedin vacuo. The crude product was purified by flash chromatography (n-hexane/EtOAc 9:1)to give 11 (9.35 g, 16.9 mmol, 44%) as a colorless oil; Rf = 0.26 (n-hexane/EtOAc 9:1); 1HNMR (CDCl3, 500 MHz) 7.66-7.70 (m, 4H), 7.35-7.44 (m, 6H), 3.73-3.78 (m, 1H), 3.62-3.68(m, 4H), 1.84-1.88 (m, 1H), 1.52-1.61 (m, 4H), 1.22-1.39 (m, 30H), 1.05 (s, 9H); 13C{1H} NMR(CDCl3, 125 MHz) 135.6, 134.2, 129.4, 127.5, 64.0, 63.1, 32.8, 32.6, 29.69, 29.67, 29.66, 29.61,29.59, 29.43, 29.38, 26.9, 25.8, 25.7, 25.6, 19.2; IR max 3370, 2923, 2853, 1590, 1464, 1428, 1389,1361, 1188, 1107, 1008, 938, 823, 738, 687, 700 cm-1; HRMS (ESI) m/z [M + H]+ calcd. forC36H61O2Si+, 553.44353; found 553.44366.
  • 71
  • [ 7735-43-5 ]
  • [ 1192540-90-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1H-imidazole / N,N-dimethyl-formamide 2: 1H-imidazole; iodine; triphenylphosphine / toluene
  • 72
  • [ 7735-43-5 ]
  • [ 18162-48-6 ]
  • [ 1616796-91-8 ]
YieldReaction ConditionsOperation in experiment
66% With 1H-imidazole In tetrahydrofuran at 60℃; for 16h; Inert atmosphere; Reflux;
42% With 1H-imidazole In tetrahydrofuran for 18h; Reflux;
  • 73
  • dimethyl 10-eicosenedioate [ No CAS ]
  • [ 7735-43-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / methanol / 4 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 15 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: 20% palladium hydroxide-activated charcoal; hydrogen / methanol; ethyl acetate / 1 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / Reflux; Inert atmosphere
  • 74
  • [ 7735-43-5 ]
  • (1-(tert-butyl dimethylsilyloxy)eicosyl)-(2’’,3’’,4’’,6’’-tetra-O-acetyl-β-D-glucopyranosyl)-(1→4)-2’,3’-di-O-acetyl-6’-O-benzyl-1’-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1H-imidazole / tetrahydrofuran / 16 h / 60 °C / Inert atmosphere; Reflux 2.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 2.2: 16 h / -40 - 20 °C / Inert atmosphere; Molecular sieve
Multi-step reaction with 3 steps 1.1: 1H-imidazole / tetrahydrofuran / 16 h / 60 °C / Inert atmosphere; Reflux 2.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 2.2: 16 h / -40 - 20 °C / Inert atmosphere; Molecular sieve 3.1: pyridine / 16 h / 0 - 20 °C / Inert atmosphere
  • 75
  • [ 7735-43-5 ]
  • (1-(tert-butyl dimethylsilyloxy)eicosyl)-(2’’,3’’,4’’,6’’-tetra-O-acetyl-β-D-glucopyranosyl)-(1→4)-2’,3’-di-O-acetyl-1’-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 1H-imidazole / tetrahydrofuran / 16 h / 60 °C / Inert atmosphere; Reflux 2.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 2.2: 16 h / -40 - 20 °C / Inert atmosphere; Molecular sieve 3.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 3.5 h / 20 °C / 750.08 Torr
Multi-step reaction with 4 steps 1.1: 1H-imidazole / tetrahydrofuran / 16 h / 60 °C / Inert atmosphere; Reflux 2.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 2.2: 16 h / -40 - 20 °C / Inert atmosphere; Molecular sieve 3.1: pyridine / 16 h / 0 - 20 °C / Inert atmosphere 4.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 3.5 h / 20 °C / 750.08 Torr
  • 76
  • [ 7735-43-5 ]
  • (1-(tert-butyl dimethylsilyloxy)eicosyl)-(2’’,3’’,4’’,6’’-tetra-O-acetyl-β-D-glucopyranosyl)-(1→4)-2’,3’-di-O-acetyl-1’-O-β-D-galactopyranosiduronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 1H-imidazole / tetrahydrofuran / 16 h / 60 °C / Inert atmosphere; Reflux 2.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 2.2: 16 h / -40 - 20 °C / Inert atmosphere; Molecular sieve 3.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 3.5 h / 20 °C / 750.08 Torr 4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; dichloromethane / 2 h / 20 °C / Inert atmosphere
Multi-step reaction with 5 steps 1.1: 1H-imidazole / tetrahydrofuran / 16 h / 60 °C / Inert atmosphere; Reflux 2.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 2.2: 16 h / -40 - 20 °C / Inert atmosphere; Molecular sieve 3.1: pyridine / 16 h / 0 - 20 °C / Inert atmosphere 4.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 3.5 h / 20 °C / 750.08 Torr 5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; dichloromethane / 2 h / 20 °C / Inert atmosphere
  • 77
  • [ 7735-43-5 ]
  • benzyl ((1-(tert-butyl dimethylsilyloxy)eicosyl)-(2’’,3’’,4’’,6’’-tetra-O-acetyl-β-D-glucopyranosyl)-(1→4)-2’,3’-di-O-acetyl-1’-O-β-D-galactopyranoside)uronate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 1H-imidazole / tetrahydrofuran / 16 h / 60 °C / Inert atmosphere; Reflux 2.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 2.2: 16 h / -40 - 20 °C / Inert atmosphere; Molecular sieve 3.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 3.5 h / 20 °C / 750.08 Torr 4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; dichloromethane / 2 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 6 steps 1.1: 1H-imidazole / tetrahydrofuran / 16 h / 60 °C / Inert atmosphere; Reflux 2.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 2.2: 16 h / -40 - 20 °C / Inert atmosphere; Molecular sieve 3.1: pyridine / 16 h / 0 - 20 °C / Inert atmosphere 4.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 3.5 h / 20 °C / 750.08 Torr 5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; dichloromethane / 2 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
  • 78
  • [ 7735-43-5 ]
  • benzyl (1-hydroxyeicosyl-(2’’,3’’,4’’,6’’-tetra-O-acetyl-β-D-glucopyranosyl)-(1→4)-2’,3’-di-O-acetyl-1’-O-β-D-galactopyranoside)uronate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 1H-imidazole / tetrahydrofuran / 16 h / 60 °C / Inert atmosphere; Reflux 2.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 2.2: 16 h / -40 - 20 °C / Inert atmosphere; Molecular sieve 3.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 3.5 h / 20 °C / 750.08 Torr 4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; dichloromethane / 2 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 6.1: acetic acid / water; tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere
Multi-step reaction with 7 steps 1.1: 1H-imidazole / tetrahydrofuran / 16 h / 60 °C / Inert atmosphere; Reflux 2.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 2.2: 16 h / -40 - 20 °C / Inert atmosphere; Molecular sieve 3.1: pyridine / 16 h / 0 - 20 °C / Inert atmosphere 4.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 3.5 h / 20 °C / 750.08 Torr 5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; dichloromethane / 2 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 7.1: acetic acid / water; tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere
  • 79
  • [ 7735-43-5 ]
  • benzyl (1-oxoeicosyl-(2’’,3’’,4’’,6’’-tetra-O-acetyl-β-D-glucopyranosyl)-(1→4)-2’,3’-di-O-acetyl-1’-O-β-D-galactopyranoside)uronate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 1H-imidazole / tetrahydrofuran / 16 h / 60 °C / Inert atmosphere; Reflux 2.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 2.2: 16 h / -40 - 20 °C / Inert atmosphere; Molecular sieve 3.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 3.5 h / 20 °C / 750.08 Torr 4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; dichloromethane / 2 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 6.1: acetic acid / water; tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere 7.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere
Multi-step reaction with 8 steps 1.1: 1H-imidazole / tetrahydrofuran / 16 h / 60 °C / Inert atmosphere; Reflux 2.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 2.2: 16 h / -40 - 20 °C / Inert atmosphere; Molecular sieve 3.1: pyridine / 16 h / 0 - 20 °C / Inert atmosphere 4.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 3.5 h / 20 °C / 750.08 Torr 5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; dichloromethane / 2 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 7.1: acetic acid / water; tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere 8.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere
  • 80
  • [ 7735-43-5 ]
  • C24H45NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen bromide / water; toluene / 48 h / 120 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 60 °C
  • 81
  • [ 7735-43-5 ]
  • 1-(20-bromoicosyl)pyrrolidine-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: hydrogen bromide / water; toluene / 48 h / 120 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 60 °C 3: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
  • 82
  • [ 7735-43-5 ]
  • 1-(20-(2,5-dioxopyrrolidin-1-yl)icosyl)pyridin-1-ium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen bromide / water; toluene / 48 h / 120 °C / Inert atmosphere 2: triphenylphosphine; diisopropyl-carbodiimide / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere 3: acetonitrile / 24 h / 90 °C / Microwave irradiation; Sealed tube
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C / Inert atmosphere 3: acetonitrile / 24 h / 90 °C / Microwave irradiation; Sealed tube
Multi-step reaction with 4 steps 1: hydrogen bromide / water; toluene / 48 h / 120 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 60 °C 3: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 4: acetonitrile / 24 h / 90 °C / Microwave irradiation; Sealed tube
  • 83
  • [ 7735-43-5 ]
  • 1-(20-(piperidin-1-yl)icosyl)pyrroidine-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen bromide / water; toluene / 48 h / 120 °C / Inert atmosphere 2: triphenylphosphine; diisopropyl-carbodiimide / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere 3: potassium carbonate / acetonitrile / 0.5 h / 90 °C / Microwave irradiation; Sealed tube
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C / Inert atmosphere 3: potassium carbonate / acetonitrile / 0.5 h / 90 °C / Microwave irradiation; Sealed tube
Multi-step reaction with 4 steps 1: hydrogen bromide / water; toluene / 48 h / 120 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 60 °C 3: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 4: potassium carbonate / acetonitrile / 0.5 h / 90 °C / Microwave irradiation; Sealed tube
  • 84
  • [ 7735-43-5 ]
  • C28H47NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen bromide / water; toluene / 48 h / 120 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 60 °C
  • 85
  • [ 7735-43-5 ]
  • 4-(20-bromoicosyl)-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: hydrogen bromide / water; toluene / 48 h / 120 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 60 °C 3: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
  • 86
  • [ 7735-43-5 ]
  • 1-(20-bromoicosyl)-2,5-dihydro-1H-pyrrole-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C / Inert atmosphere 3: 1 h / 0.75 Torr / Heating
Multi-step reaction with 4 steps 1: hydrogen bromide / water; toluene / 48 h / 120 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 60 °C 3: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 4: 1 h / 0.75 Torr / Heating
  • 87
  • [ 7735-43-5 ]
  • 1-(20-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)icosyl)pyridin-1-ium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C / Inert atmosphere 3: 1 h / 0.75 Torr / Heating 4: acetonitrile / 24 h / 90 °C / Microwave irradiation; Sealed tube
Multi-step reaction with 5 steps 1: hydrogen bromide / water; toluene / 48 h / 120 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 60 °C 3: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 4: 1 h / 0.75 Torr / Heating 5: acetonitrile / 24 h / 90 °C / Microwave irradiation; Sealed tube
  • 88
  • [ 7735-43-5 ]
  • 4-(20-(piperidin-1-yl)icosyl)-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C / Inert atmosphere 3: acetonitrile / 0.5 h / 90 °C / Microwave irradiation; Sealed tube
Multi-step reaction with 4 steps 1: hydrogen bromide / water; toluene / 48 h / 120 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 60 °C 3: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 4: acetonitrile / 0.5 h / 90 °C / Microwave irradiation; Sealed tube
  • 89
  • [ 7735-43-5 ]
  • 1-(20-(piperidin-1-yl)icosyl)-2,5-dihydro-1H-pyrrole-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C / Inert atmosphere 3: acetonitrile / 0.5 h / 90 °C / Microwave irradiation; Sealed tube 4: 1 h / 0.75 Torr / Heating
Multi-step reaction with 5 steps 1: hydrogen bromide / water; toluene / 48 h / 120 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 60 °C 3: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 4: acetonitrile / 0.5 h / 90 °C / Microwave irradiation; Sealed tube 5: 1 h / 0.75 Torr / Heating
  • 90
  • [ 7735-43-5 ]
  • [ 1192540-89-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
  • 91
  • [ 7735-43-5 ]
  • [ 58479-61-1 ]
  • [ 1192540-89-8 ]
  • 2,2,27,27‐tetramethyl‐3,3,26,26‐tetraphenyl‐4,25‐dioxa‐3,26‐disilaoctacosane [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 45% 2: 23% Stage #1: 1,20-eicosanediol; tert-butylchlorodiphenylsilane With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.25h; Inert atmosphere; Stage #2: In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
  • 92
  • [ 7735-43-5 ]
  • [ 98-59-9 ]
  • [ 83932-91-6 ]
YieldReaction ConditionsOperation in experiment
86% With pyridine In chloroform at 0 - 5℃; for 18.5h; Schlenk technique;
  • 93
  • [ 7735-43-5 ]
  • (1,22-<SUP>13</SUP>C)docosanedinitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / chloroform / 18.5 h / 0 - 5 °C / Schlenk technique 2: N,N-dimethyl-formamide / 120 h / 20 °C
  • 94
  • [ 7735-43-5 ]
  • (1,22-<SUP>13</SUP>C)docosanedioic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / chloroform / 18.5 h / 0 - 5 °C / Schlenk technique 2: N,N-dimethyl-formamide / 120 h / 20 °C 3: hydrogenchloride; acetic acid / 24 h / Reflux
  • 95
  • [ 7735-43-5 ]
  • C30H59Br [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen bromide; acetic anhydride 2: magnesium / tetrahydrofuran
  • 96
  • [ 7735-43-5 ]
  • [1-(13)C]hentriacont-30-enenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen bromide; acetic anhydride 2: magnesium / tetrahydrofuran 3: dimethyl sulfoxide / 72 h / 85 °C
  • 97
  • [ 7735-43-5 ]
  • [1-(13)C]hentriacont-30-enoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; acetic anhydride 2: magnesium / tetrahydrofuran 3: dimethyl sulfoxide / 72 h / 85 °C 4: sodium hydroxide / ethanol / 24 h / Reflux
  • 98
  • [ 7735-43-5 ]
  • [1-(13)C]hentricont-30-en-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; acetic anhydride 2: magnesium / tetrahydrofuran 3: dimethyl sulfoxide / 72 h / 85 °C 4: sodium hydroxide / ethanol / 24 h / Reflux 5: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere; Reflux
  • 99
  • [ 7735-43-5 ]
  • [1-(13)C]hentriacont-30-enyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: hydrogen bromide; acetic anhydride 2: magnesium / tetrahydrofuran 3: dimethyl sulfoxide / 72 h / 85 °C 4: sodium hydroxide / ethanol / 24 h / Reflux 5: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere; Reflux 6: pyridine / 3 h / 0 - 70 °C
  • 100
  • [ 7735-43-5 ]
  • [30-(13)C]-30-acetoxytriacontanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: hydrogen bromide; acetic anhydride 2: magnesium / tetrahydrofuran 3: dimethyl sulfoxide / 72 h / 85 °C 4: sodium hydroxide / ethanol / 24 h / Reflux 5: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere; Reflux 6: pyridine / 3 h / 0 - 70 °C 7: potassium permanganate; sulfuric acid; acetic acid / water; dichloromethane / 75 h / 20 °C / Cooling with ice
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