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[ CAS No. 72345-23-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 72345-23-4
Chemical Structure| 72345-23-4
Chemical Structure| 72345-23-4
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Product Details of [ 72345-23-4 ]

CAS No. :72345-23-4 MDL No. :MFCD00064276
Formula : C5H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :GTCCGKPBSJZVRZ-WHFBIAKZSA-N
M.W : 104.15 Pubchem ID :6950200
Synonyms :

Calculated chemistry of [ 72345-23-4 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 28.47
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.49
Log Po/w (XLOGP3) : 0.08
Log Po/w (WLOGP) : 0.14
Log Po/w (MLOGP) : 0.23
Log Po/w (SILICOS-IT) : 0.03
Consensus Log Po/w : 0.39

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.4
Solubility : 41.1 mg/ml ; 0.394 mol/l
Class : Very soluble
Log S (Ali) : -0.48
Solubility : 34.2 mg/ml ; 0.328 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.07
Solubility : 121.0 mg/ml ; 1.16 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 72345-23-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 72345-23-4 ]

* 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 [ 72345-23-4 ]

[ 72345-23-4 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 102-52-3 ]
  • [ 72345-23-4 ]
  • [ 116185-04-7 ]
YieldReaction ConditionsOperation in experiment
95% With o-toluenesulfonic acid In toluene
95% With toluene-4-sulfonic acid In toluene Heating;
  • 2
  • [ 66774-71-8 ]
  • [ 72345-23-4 ]
  • (20S)-des-A,B-8β-(benzoyloxy)-20-<(4'S,6'S)-4',6'-dimethyl-1',3'-dioxan-2'-yl>pregnane [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With boron trifluoride diethyl etherate In tetrahydrofuran for 16h; Ambient temperature;
  • 3
  • [ 59830-60-3 ]
  • [ 72345-23-4 ]
  • [ 113283-75-3 ]
YieldReaction ConditionsOperation in experiment
95% With toluene-4-sulfonic acid In dichloromethane Heating;
  • 4
  • [ 108-94-1 ]
  • [ 72345-23-4 ]
  • [ 129098-50-6 ]
YieldReaction ConditionsOperation in experiment
82.9% With collidinium p-toluene sulfonate In benzene for 48h; Heating;
  • 5
  • [ 72345-23-4 ]
  • [ 106673-33-0 ]
  • (4S,6S)-2-(7-(benzyloxy)heptyl)-4,6-dimethyl-1,3-dioxane [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With pyridinium p-toluenesulfonate In benzene for 2h; Heating;
  • 6
  • [ 72345-23-4 ]
  • [ 144346-77-0 ]
  • [ 144408-52-6 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid In benzene at 75℃; for 0.5h; Yield given;
  • 7
  • [ 72345-23-4 ]
  • [ 88803-14-9 ]
  • [ 88803-15-0 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran Linde 4A molecular sieves; Yield given;
  • 8
  • [ 72345-23-4 ]
  • [ 18162-48-6 ]
  • [ 156659-87-9 ]
YieldReaction ConditionsOperation in experiment
95% With sodium hydride In tetrahydrofuran for 2.75h; Ambient temperature;
With sodium hydride 1) THF, 2 h, RT, 2) THF, 45 min; Yield given. Multistep reaction;
  • 9
  • [ 72345-23-4 ]
  • [ 1079-66-9 ]
  • (+)-(2S,4S)-2,4-bis<(diphenylphosphinyl)oxy>pentane [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With pyridine In tetrahydrofuran a) 0 deg C to room temperature, b) overnight;
  • 10
  • [ 123-54-6 ]
  • [ 72345-23-4 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride; <NH2Et2><<RuCl(S-BINAP)>2(μ-Cl)3>; hydrogen In methanol at 60℃; for 0.666667h; other diones, also without HCl, var. time, temp. and pressure;
95% With hydrogenchloride; <NH2Et2><<RuCl(S-BINAP)>2(μ-Cl)3>; hydrogen In methanol at 60℃; for 0.666667h;
44% With hydrogen; acetic acid In tetrahydrofuran at 100℃;
42% With dichloro(benzene)ruthenium(II) dimer; hydrogen; (2S,4S)-2,4-bis(diphenylphosphino)pentane In methanol at 80℃; for 16h;
With <RuCl2(PPh3)><(S)-2,2'-dimethyl-6,6'-bis(diphenylphosphino)biphenyl>; hydrogen In ethanol at 40℃; for 60h;
With hydrogen In methanol for 64h; Ambient temperature;
With hydrogen bromide; hydrogen; (S)-5',6'-benzo-6-methoxy-2,2'-bis(diphenylphosphanyl)biphenyl In methanol at 50℃; for 72h;
99 % ee With hydrogenchloride; hydrogen In ethanol; water at 80℃; for 16.5h;
96 % ee With hydrogenchloride; diiodo(p-cymene)ruthenium(II) dimer; (R)-1-{(RFc)-2-[2-(diphenylphosphino)phenyl]ferrocenyl}ethylbis[3,5-bis-(trifluoromethyl)phenyl]phosphine; hydrogen In methanol at 80℃; for 17h; Autoclave; enantioselective reaction;
98% ee With hydrogenchloride; bis(norbornadiene)rhodium(l)tetrafluoroborate; (Sp)-2-[(R)-1-diphenylphosphinoethyl]-(Sp)-2″-diphenylphosphino-1,1″-biferrocene; hydrogen In methanol; water at 80℃; for 17h; Inert atmosphere; Autoclave;

  • 12
  • [ 123-54-6 ]
  • [ 3950-21-8 ]
  • [ 72345-23-4 ]
YieldReaction ConditionsOperation in experiment
1: 0.1 % Chromat. 2: 99.0 % Chromat. With tetraphenylarsonium chloride; hydrogen In ethanol at 50℃; for 24h; Title compound not separated from byproducts;
  • 13
  • [ 123-54-6 ]
  • [ 42075-32-1 ]
  • [ 72345-23-4 ]
YieldReaction ConditionsOperation in experiment
With L-Tartaric acid; hydrogen In tetrahydrofuran; water
With D-tartaric acid; hydrogen In tetrahydrofuran
With hydrogen In methanol at 80℃; for 64h; Title compound not separated from byproducts;
With chiral 1,5-diphenylphosphanylferrocene compound; hydrogen bromide; hydrogen In ethanol at 50℃; for 8h;
With hydrogen In methanol at 80℃; for 17h;
With hydrogenchloride; diiodo(p-cymene)ruthenium(II) dimer; (S(p),S(p))-2,2''-bis(diphenylphosphino)-1,1''-biferrocene; hydrogen In ethanol; water at 80℃; for 19h; Autoclave; optical yield given as %ee; enantioselective reaction;
85 % ee With hydrogenchloride; diiodo(p-cymene)ruthenium(II) dimer; (SFc)-2-{(R)-1-bis[3,5-bis(trifluoromethyl)phenyl]phosphinoethyl}-(RFc)-2′′-diphenylphosphino-1,1′′-biferrocene; hydrogen In methanol at 80℃; for 17h; Autoclave;
85 % ee With hydrogenchloride; diiodo(p-cymene)ruthenium(II) dimer; (S)-1-{(SFc)-2-[2-(diphenylphosphino)phenyl]ferrocenyl}ethylbis[3,5-bis-(trifluoromethyl)phenyl]phosphine; hydrogen In methanol at 80℃; for 17h; Autoclave;
85% ee With hydrogenchloride; bis(norbornadiene)rhodium(l)tetrafluoroborate; (R)-1-[2-(2'-diphenylphosphinophenyl)ferrocenyl]ethyldiphenylphosphine; hydrogen In methanol; water at 80℃; for 17h; Inert atmosphere; Autoclave;
80% ee With hydrogenchloride; bis(norbornadiene)rhodium(l)tetrafluoroborate; (Sp)-2-[(R)-1-diphenylphosphinoethyl]-(Rp)-2″-diphenylphosphino-1,1″-biferrocene; hydrogen In methanol; water at 80℃; for 17h; Inert atmosphere; Autoclave;

Reference: [1]Bakos, Jozsef; Toth, Imre; Heil, Balint; Marko, Laszlo [Journal of Organometallic Chemistry, 1985, vol. 279, p. 23 - 30]
[2]Bakos, Jozsef; Toth, Imre; Heil, Balint; Marko, Laszlo [Journal of Organometallic Chemistry, 1985, vol. 279, p. 23 - 30]
[3]Marinetti, Angela; Genet, Jean-Pierre; Jus, Sebastien; Blanc, Delphine; Ratovelomanana-Vidal, Virginie [Chemistry - A European Journal, 1999, vol. 5, # 4, p. 1160 - 1165]
[4]Ireland, Tania; Tappe, Katja; Grossheimann, Gabi; Knochel, Paul [Chemistry - A European Journal, 2002, vol. 8, # 4, p. 843 - 852]
[5]Sturm, Thomas; Weissensteiner, Walter; Spindler, Felix [Advanced Synthesis and Catalysis, 2003, vol. 345, # 1-2, p. 160 - 164]
[6]Location in patent: experimental part Espino, Gustavo; Xiao, Li; Puchberger, Michael; Mereiter, Kurt; Spindler, Felix; Manzano, Blanca R.; Jalon, Felix A.; Weissensteiner, Walter [Dalton Transactions, 2009, # 15, p. 2751 - 2763]
[7]Zirakzadeh, Afrooz; Gross, Manuela A.; Wang, Yaping; Mereiter, Kurt; Spindler, Felix; Weissensteiner, Walter [Organometallics, 2013, vol. 32, # 4, p. 1075 - 1084]
[8]Zirakzadeh, Afrooz; Gross, Manuela A.; Wang, Yaping; Mereiter, Kurt; Spindler, Felix; Weissensteiner, Walter [Organometallics, 2013, vol. 32, # 4, p. 1075 - 1084]
[9]Zirakzadeh, Afrooz; Gross, Manuela A.; Wang, Yaping; Mereiter, Kurt; Weissensteiner, Walter [Organometallics, 2014, vol. 33, # 8, p. 1945 - 1952]
[10]Zirakzadeh, Afrooz; Gross, Manuela A.; Wang, Yaping; Mereiter, Kurt; Weissensteiner, Walter [Organometallics, 2014, vol. 33, # 8, p. 1945 - 1952]
  • 14
  • [ 72345-23-4 ]
  • [ 183021-91-2 ]
  • (S)-2-Benzyloxycarbonylamino-3-[4-((4S,6S)-4,6-dimethyl-[1,3]dioxan-2-yl)-phenyl]-propionic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With toluene-4-sulfonic acid In diethyl ether for 5h; Heating;
  • 15
  • [ 72345-23-4 ]
  • [ 177570-11-5 ]
YieldReaction ConditionsOperation in experiment
96% With triethylamine; trichlorophosphate In benzene for 15h; Ambient temperature;
  • 16
  • [ 72345-23-4 ]
  • (S)-(1,1'-binaphthyl-2,2'-dioxy)chlorophosphine [ No CAS ]
  • (2S,4S)-2,4-bis[(S)-dinaphtho[d,f][1,3,2]dioxaphosphepin-6-yloxy]pentane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In toluene
  • 17
  • [ 72345-23-4 ]
  • [ 217816-86-9 ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine; phosphorus trichloride In diethyl ether at -20℃;
  • 18
  • [ 72345-23-4 ]
  • [ 187995-42-2 ]
  • [2-((4S,6S)-4,6-Dimethyl-[1,3]dioxan-2-yl)-allyl]-trimethyl-silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With toluene-4-sulfonic acid In benzene Heating;
  • 19
  • [ 123-54-6 ]
  • [ 3950-21-8 ]
  • [ 42075-32-1 ]
  • [ 72345-23-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In methanol at 80℃; for 60h; Title compound not separated from byproducts;
  • 20
  • [ 2033-24-1 ]
  • [ 72345-23-4 ]
  • 10-undecenoic acid [ No CAS ]
  • (Z)-3-Oxo-tetradec-12-enoic acid (1S,3S)-3-hydroxy-1-methyl-butyl ester [ No CAS ]
  • [ 261178-59-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 10-undecenoic acid With thionyl chloride In N,N-dimethyl-formamide; benzene for 2h; Thermolysis; Stage #2: cycl-isopropylidene malonate With dmap In dichloromethane at 0 - 20℃; Stage #3: (2S,4S)-pentane-2,4-diol In benzene for 3h; Thermolysis; Title compound not separated from byproducts;
  • 21
  • [ 72345-23-4 ]
  • [ 347840-57-7 ]
  • [ 347840-58-8 ]
YieldReaction ConditionsOperation in experiment
80% With pyridinium p-toluenesulfonate In benzene at 80℃; for 0.333333h;
  • 22
  • [ 72345-23-4 ]
  • [ 100-20-9 ]
  • (S)-5,5'-diamino-BINAP [ No CAS ]
  • Polymer; Monomer(s): (S)-5,5\-diamino-BINAP; (2S,4S)-pentanediol; terephthaloyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In 1,2-dichloro-ethane
  • 23
  • [ 72345-23-4 ]
  • [ 100-20-9 ]
  • (S)-5,5'-diamino-BINAP [ No CAS ]
  • Polymer; Monomer(s): (R)-5,5\-diamino-BINAP; (2S,4S)-pentanediol; terephthaloyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In 1,2-dichloro-ethane
  • 24
  • [ 72345-23-4 ]
  • (S)-(1,1'-binaphthyl-2,2'-dioxy)chlorophosphine [ No CAS ]
  • (2S,4S)-2,4-bis[((S)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-2-yl)oxy]pentane [ No CAS ]
YieldReaction ConditionsOperation in experiment
97.9% With triethylamine In toluene at 0 - 20℃;
  • 25
  • [ 72345-23-4 ]
  • 4-chloro-8,9,10,11,12,13,14,15-octahydro-3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalene [ No CAS ]
  • (2S,4S)-2,4-bis[(R,S)-5,5',6,6',7,7',8,8'-octahydro-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-2-yloxy]pentane [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With triethylamine In toluene at 0 - 20℃;
  • 26
  • [ 72345-23-4 ]
  • (11bR)-4-chloro-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1',2'-f]-[1,3,2]dioxaphosphepine [ No CAS ]
  • (2S,4S)-2,4-bis[(R,S)-5,5',6,6',7,7',8,8'-octahydro-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-2-yloxy]pentane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In toluene at 0 - 20℃; Title compound not separated from byproducts;
  • 28
  • [ 72345-23-4 ]
  • [ 108-95-2 ]
  • [ 118711-25-4 ]
YieldReaction ConditionsOperation in experiment
93.1% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 24h;
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃;
  • 29
  • [ 72345-23-4 ]
  • [ 56813-57-1 ]
  • 2-(1,3-dioxo-1<i>H</i>,3<i>H</i>-benzo[<i>de</i>]isoquinolin-2-yl)-benzoic acid 3-hydroxy-1-methyl-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; dmap at 20℃; for 4h;
  • 30
  • [ 72345-23-4 ]
  • [ 6630-33-7 ]
  • [ 696643-13-7 ]
YieldReaction ConditionsOperation in experiment
90% With toluene-4-sulfonic acid In benzene for 5h; Heating;
With pyridinium p-toluenesulfonate In toluene for 3.5h; Heating;
  • 31
  • [ 358-23-6 ]
  • [ 72345-23-4 ]
  • Trifluoro-methanesulfonic acid (1S,3S)-1-methyl-3-trifluoromethanesulfonyloxy-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With 2,6-dimethylpyridine In dichloromethane at -78℃; for 2.5h;
With 2,6-dimethylpyridine
  • 32
  • [ 3966-32-3 ]
  • [ 72345-23-4 ]
  • (R)-Methoxy-phenyl-acetic acid (1S,3S)-3-((R)-2-methoxy-2-phenyl-acetoxy)-1-methyl-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 2h;
  • 33
  • [ 26164-26-1 ]
  • [ 72345-23-4 ]
  • (S)-Methoxy-phenyl-acetic acid (1S,3S)-3-((S)-2-methoxy-2-phenyl-acetoxy)-1-methyl-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 2h;
  • 34
  • [ 72345-23-4 ]
  • [ 183388-44-5 ]
  • (S)-Anthracen-9-yl-methoxy-acetic acid (1S,3S)-3-((S)-2-anthracen-9-yl-2-methoxy-acetoxy)-1-methyl-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 2h;
  • 35
  • [ 72345-23-4 ]
  • [ 156942-68-6 ]
  • (R)-Anthracen-9-yl-methoxy-acetic acid (1S,3S)-3-((R)-2-anthracen-9-yl-2-methoxy-acetoxy)-1-methyl-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 2h;
  • 36
  • [ 85920-63-4 ]
  • [ 72345-23-4 ]
  • [ 736177-39-2 ]
  • 37
  • [ 452-72-2 ]
  • [ 72345-23-4 ]
  • [ 914461-74-8 ]
  • 38
  • [ 72345-23-4 ]
  • [ 798568-75-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,6-lutidine 2: [(Me2N)2CNH2][N3]
Multi-step reaction with 2 steps 1: 100 percent / 2,6-dimethylpyridine / CH2Cl2 / 2.5 h / -78 °C 2: 100 percent / [(Me2N)2CNH2]N3 / CH2Cl2 / 0 - 20 °C
  • 39
  • [ 72345-23-4 ]
  • N,N-diphenyl-(2R,4R)-pentanediamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 2,6-lutidine 2.1: [(Me2N)2CNH2][N3] 3.2: aq. NaOH
Multi-step reaction with 3 steps 1.1: 100 percent / 2,6-dimethylpyridine / CH2Cl2 / 2.5 h / -78 °C 2.1: 100 percent / [(Me2N)2CNH2]N3 / CH2Cl2 / 0 - 20 °C 3.1: toluene / 24 h / 0 - 20 °C 3.2: 76 percent / MeOH / toluene / 0.75 h
  • 40
  • [ 72345-23-4 ]
  • [ 695816-49-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 90 percent / p-TsOH*H2O / benzene / 5 h / Heating 2: 73 percent / N-diisopropylethylamine; dppb / Pd(OAc)2 / dimethylsulfoxide / 100 °C 3: 32.6 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.5 h / 20 °C
  • 41
  • [ 72345-23-4 ]
  • [ 695816-48-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / p-TsOH*H2O / benzene / 5 h / Heating 2: 73 percent / N-diisopropylethylamine; dppb / Pd(OAc)2 / dimethylsulfoxide / 100 °C
  • 42
  • [ 72345-23-4 ]
  • 2-[2-((2R,5R)-dimethylphospholan-1-yl)phenyl]-(4S,6S)-dimethyl-[1,3]dioxane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 90 percent / p-TsOH*H2O / benzene / 5 h / Heating 2.1: 73 percent / N-diisopropylethylamine; dppb / Pd(OAc)2 / dimethylsulfoxide / 100 °C 3.1: 32.6 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.5 h / 20 °C 4.1: KH / tetrahydrofuran / 1.5 h / -30 °C 4.2: tetrahydrofuran / 2 h / 20 °C 4.3: 36 percent / KH / tetrahydrofuran / 2 h / 20 °C
  • 43
  • [ 72345-23-4 ]
  • 2-[2-((2S,5S)-dimethylphospholan-1-yl)phenyl]-(4S,6S)-dimethyl-[1,3]dioxane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 90 percent / p-TsOH*H2O / benzene / 5 h / Heating 2.1: 73 percent / N-diisopropylethylamine; dppb / Pd(OAc)2 / dimethylsulfoxide / 100 °C 3.1: 32.6 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.5 h / 20 °C 4.1: KH / tetrahydrofuran / 1.5 h / -30 °C 4.2: tetrahydrofuran / 2 h / 20 °C 4.3: 38 percent / KH / tetrahydrofuran / 2 h / 20 °C
  • 44
  • [ 72345-23-4 ]
  • [ 496042-32-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C
  • 45
  • [ 72345-23-4 ]
  • [ 496042-33-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C
  • 46
  • [ 72345-23-4 ]
  • [ 496042-34-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 95.5 percent / tetrahydrofuran; hexane / -78 - 20 °C
  • 47
  • [ 72345-23-4 ]
  • [ 496042-35-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 95.5 percent / tetrahydrofuran; hexane / -78 - 20 °C 5.1: 3.78 g / H2O2 / acetone; H2O / 0 °C
  • 48
  • [ 72345-23-4 ]
  • [ 496042-36-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 95.5 percent / tetrahydrofuran; hexane / -78 - 20 °C 5.1: 3.78 g / H2O2 / acetone; H2O / 0 °C 6.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / -78 °C 6.2: 1,2-diidoethane / tetrahydrofuran / -78 - 20 °C
  • 49
  • [ 72345-23-4 ]
  • (S)-[5,5',6,6'-bis(2R,4R-pentadioxy)]-(2,2')-bis(diphenylphosphino)-(1,1')-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 95.5 percent / tetrahydrofuran; hexane / -78 - 20 °C 5.1: 3.78 g / H2O2 / acetone; H2O / 0 °C 6.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / -78 °C 6.2: 1,2-diidoethane / tetrahydrofuran / -78 - 20 °C 7.1: Cu powder / dimethylformamide / 12 h / 140 °C 8.1: 89.5 percent / trichlorosilane; tributylamine / toluene / Heating
  • 50
  • [ 72345-23-4 ]
  • (R)-[5,5',6,6'-bis(2R,4R-pentadioxy)]-(2,2')-bis(diphenylphosphino)-(1,1')-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 95.5 percent / tetrahydrofuran; hexane / -78 - 20 °C 5.1: 3.78 g / H2O2 / acetone; H2O / 0 °C 6.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / -78 °C 6.2: 1,2-diidoethane / tetrahydrofuran / -78 - 20 °C 7.1: Cu powder / dimethylformamide / 12 h / 140 °C 8.1: 92 percent / trichlorosilane; tributylamine / toluene / Heating
  • 51
  • [ 72345-23-4 ]
  • (R)-[5,5',6,6'-bis(2R,4R-pentadioxy)]-(2,2')-bis(diphenylphosphine oxide)-(1,1')-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 95.5 percent / tetrahydrofuran; hexane / -78 - 20 °C 5.1: 3.78 g / H2O2 / acetone; H2O / 0 °C 6.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / -78 °C 6.2: 1,2-diidoethane / tetrahydrofuran / -78 - 20 °C 7.1: Cu powder / dimethylformamide / 12 h / 140 °C
  • 52
  • [ 72345-23-4 ]
  • (S)-[5,5',6,6'-bis(2R,4R-pentadioxy)]-(2,2')-bis(diphenylphosphine oxide)-(1,1')-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 95.5 percent / tetrahydrofuran; hexane / -78 - 20 °C 5.1: 3.78 g / H2O2 / acetone; H2O / 0 °C 6.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / -78 °C 6.2: 1,2-diidoethane / tetrahydrofuran / -78 - 20 °C 7.1: Cu powder / dimethylformamide / 12 h / 140 °C
  • 53
  • [ 72345-23-4 ]
  • [ 428509-73-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 85 percent / diethyl azodicarboxylate; PPh3 / tetrahydrofuran / 20 °C 2: 75 percent / diethyl azodicarboxylate; PPh3 / tetrahydrofuran / 20 °C
  • 54
  • [ 72345-23-4 ]
  • C22H22O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 85 percent / diethyl azodicarboxylate; PPh3 / tetrahydrofuran / 20 °C 2.1: 75 percent / diethyl azodicarboxylate; PPh3 / tetrahydrofuran / 20 °C 3.1: nBuLi / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: CuCN / tetrahydrofuran; hexane / 2 h / -78 °C 3.3: 50 percent / O2 / tetrahydrofuran; hexane / -78 °C
  • 55
  • [ 72345-23-4 ]
  • [ 116210-21-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / p-TsOH / toluene / Heating 2: 90 percent / BH3*THF / tetrahydrofuran / 96 h / Heating
Multi-step reaction with 2 steps 1: 95 percent / toluenesulfonic acid / toluene 2: 90 percent / BH2Cl*SMe2 / diethyl ether / 12 h / Ambient temperature
  • 56
  • [ 72345-23-4 ]
  • [ 156706-64-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1: 1) NaH (60percent in oil) / 1) THF, 2 h, RT, 2) THF, 45 min 2: 84 percent / pyridine / 72 h / 4 °C 3: 85 percent / hexamethylphosphoric acid triamide / 0 deg C, 30 min; RT, 24 h 4: 1) DIBAL-H (0.93 M in hexane), 2) H2O, KHSO4 / 1) CH2Cl2, -78 deg C, 1.5 h, 2) CH2Cl2, 78 deg C to RT 5: CH2Cl2 / 72 h / Ambient temperature 6: 89 percent / DIBAL-H (1.5 M in hexane) / CH2Cl2 / 0.5 h / -78 °C 7: PPh3, I2, imidazole / acetonitrile; tetrahydrofuran / 0.17 h / -10 °C 8: 1) 1.0 M sodium hexamethyldisilazide in THF / 1)THF, -78 deg C, 1 h, 2) THF, -72 deg C, 24 h 9: 96 percent / LiOH, 30percent H2O2 / tetrahydrofuran / 1 h / 0 °C 10: 85 percent / DCC, DMAP / CH2Cl2 / 0 deg C, 1 h; RT, 24 h 11: 84 percent / TBAF / tetrahydrofuran / 16 h / Ambient temperature 12: 1) PPh3, DEAD, HCOOH, 2) MeOH, aq. NaHCO3 / 1) Et2O, 0 deg C 10 min then RT, 1 h 13: 95 percent / PPh3, DEAD / tetrahydrofuran / 0 deg C, 30 min; RT, 36 h
Multi-step reaction with 12 steps 1: 1) NaH (60percent in oil) / 1) THF, 2 h, RT, 2) THF, 45 min 2: 84 percent / pyridine / 72 h / 4 °C 3: 85 percent / hexamethylphosphoric acid triamide / 0 deg C, 30 min; RT, 24 h 4: 1) DIBAL-H (0.93 M in hexane), 2) H2O, KHSO4 / 1) CH2Cl2, -78 deg C, 1.5 h, 2) CH2Cl2, 78 deg C to RT 5: CH2Cl2 / 72 h / Ambient temperature 6: 89 percent / DIBAL-H (1.5 M in hexane) / CH2Cl2 / 0.5 h / -78 °C 7: PPh3, I2, imidazole / acetonitrile; tetrahydrofuran / 0.17 h / -10 °C 8: 1) 1.0 M sodium hexamethyldisilazide in THF / 1)THF, -78 deg C, 1 h, 2) THF, -72 deg C, 24 h 9: 96 percent / LiOH, 30percent H2O2 / tetrahydrofuran / 1 h / 0 °C 10: 85 percent / DCC, DMAP / CH2Cl2 / 0 deg C, 1 h; RT, 24 h 11: 84 percent / TBAF / tetrahydrofuran / 16 h / Ambient temperature 12: 1) carbonyldiimidazole / 1) THF, 0 deg C, 15 min then RT, 2 h, 2) THF, RT, 30 h, 5 kbar
Multi-step reaction with 10 steps 1: 95 percent / NaH / tetrahydrofuran / 2.75 h / Ambient temperature 2: 84 percent / pyridine / 72 h / 4 °C 3: 85 percent / hexamethylphosphoric acid triamide / 18 h / Ambient temperature 4: 1.) diisobutylaluminum hydride / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, rt., 93 h 5: 89 percent / diisobutylaluminum hydride / CH2Cl2 / 1.5 h / -78 °C 6: iodine, triphenylphosphine, imidazole / tetrahydrofuran; acetonitrile / 0.17 h / -10 °C 7: 2.) LiOH, 30 percent H2O2, H2O / 1.) THF, -72 deg C, 24 h, 2.) THF, 0 deg C, 1 h 8: 85 percent / DCC, DMAP / CH2Cl2 / 9 h / Ambient temperature 9: 84 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 16 h / Ambient temperature 10: 30 h / 3750300 Torr / Ambient temperature
Multi-step reaction with 11 steps 1: 95 percent / NaH / tetrahydrofuran / 2.75 h / Ambient temperature 2: 84 percent / pyridine / 72 h / 4 °C 3: 85 percent / hexamethylphosphoric acid triamide / 18 h / Ambient temperature 4: 1.) diisobutylaluminum hydride / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, rt., 93 h 5: 89 percent / diisobutylaluminum hydride / CH2Cl2 / 1.5 h / -78 °C 6: iodine, triphenylphosphine, imidazole / tetrahydrofuran; acetonitrile / 0.17 h / -10 °C 7: 2.) LiOH, 30 percent H2O2, H2O / 1.) THF, -72 deg C, 24 h, 2.) THF, 0 deg C, 1 h 8: 85 percent / DCC, DMAP / CH2Cl2 / 9 h / Ambient temperature 9: 84 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 16 h / Ambient temperature 10: 86 percent / diethyl azodicarboxylate, triphenylphosphine, formic acid / diethyl ether / 1 h / Ambient temperature 11: 95 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 36 h / Ambient temperature; other tripeptide derivatives

  • 57
  • [ 72345-23-4 ]
  • [ 96183-46-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 49 percent / pyridine 2: 1.) Li / 1.) THF, 2.) THF, from -10 deg C to RT
Multi-step reaction with 2 steps 1: pyridine / 0 °C / overnight 2: 1.) Li / 1.) THF, reflux, 3 h; 2.) THF, 0 deg C, then Rt, overnight
  • 58
  • [ 72345-23-4 ]
  • [ 88803-17-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: oxalic acid / tetrahydrofuran / Linde 4A molecular sieves 2: 82 percent / 1.) titanium tetrachloride, 2,4,6-trimethylpyridine, 2.) 1 M hydrochloric acid / CH2Cl2 / 1.) -78 degC, 5 min., 2.) -78 degC to r.t. 3: pyridinium chlorochromate / CH2Cl2 / 18 h / 25 °C
  • 59
  • [ 72345-23-4 ]
  • [ 88803-16-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalic acid / tetrahydrofuran / Linde 4A molecular sieves 2: 82 percent / 1.) titanium tetrachloride, 2,4,6-trimethylpyridine, 2.) 1 M hydrochloric acid / CH2Cl2 / 1.) -78 degC, 5 min., 2.) -78 degC to r.t.
  • 60
  • [ 72345-23-4 ]
  • (2S,4S)-4-((3aS,4S,7aR)-7a-Methyl-1-vinylidene-octahydro-inden-4-yloxy)-pentan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalic acid / tetrahydrofuran / Linde 4A molecular sieves 2: 9 percent / 1.) titanium tetrachloride, 2,4,6-trimethylpyridine, 2.) 1 M hydrochloric acid / CH2Cl2 / 1.) -78 degC, 5 min., 2.) -78 degC to r.t.
  • 61
  • [ 2033-42-3 ]
  • [ 72345-23-4 ]
  • [ 428509-72-2 ]
  • 62
  • [ 52698-46-1 ]
  • [ 865-47-4 ]
  • [ 72345-23-4 ]
  • 2-isopropyl-2-methoxy-4(R),6(R)-dimethyl-1,3-dioxane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridinium p-toluenesulfonate; In toluene; (d) A mixture of 15.6 g (0.105 mol) of <strong>[52698-46-1]1,1,1-trimethoxyisobutane</strong>, 10 g (0.0962 mol) of 2(S),4(S)-dihydroxypentane, and 251 mg of PPTS in 150 ml of toluene (dried over 3 A sieves) was allowed to reflux under argon for 11/2 hours while azeotroping water formed using the Dean-Stark trap. The reaction mixture was cooled, 1.2 g of potassium tert. butoxide was added, and the solvent was distilled. Ether (100 ml) was added to the residue, passed through a supercel pad eluding with 300 ml of ether, and the combined solvent was distilled in vacuo (<40 C.). The residue was distilled to afford 14.3 g (79.4%) of 2-isopropyl-2-methoxy-4(R),6(R)-dimethyl-1,3-dioxane, b.p. 78-82 C./15 mm.
  • 63
  • [ 72345-23-4 ]
  • [ 500131-50-0 ]
  • [ 863974-08-7 ]
YieldReaction ConditionsOperation in experiment
78% for 0.333333h; Microwave irradiation; 1 (2S,4S)-Pentane-2,4-diol (1 mmol), dioxane (1 mL), and fluorinating agent A (1 mmol) were placed in a Teflon (registered trademark) PFA container and sufficiently mixed. The mixture was placed in a microwave irradiator (product of Sharp, 2.45 GHz, 500 W) and irradiated with a microwave for 10 minutes. After cooling, fluorinating agent A (1 mmol) was further added to the mixture, and the resultant mixture was irradiated with a microwave for another 10 minutes. The reaction mixture was cooled to room temperature, and poured into a saturated aqueous sodium hydrogencarbonate solution. The system was subjected to extraction with ether (40 mL, three times). The ether solution was dried over magnesium sulfate, concentrated, and purified through silica gel column chromatography, whereby (2S,4R)-2-(3-methylbenzoyloxy)-4-fluoropentane, which is a target compound, was produced (yield: 78%, optical purity: 100%).
  • 64
  • [ 84355-13-5 ]
  • [ 72345-23-4 ]
  • [ 107951-71-3 ]
YieldReaction ConditionsOperation in experiment
80% In dichloromethane at 20℃; for 19h; 194.b (194b); To a CH2Cl2 (5 mL) solution of (2S,4S)-(+)-pentanediol (209 mg, 2 mmol) was added the salt (1.90 g, 3.1 eq) from reaction 194a at room temperature. The mixture was stirred for 19 h, filtered through a short bed of silica gel and concentrated to give the crude bis(O-trimethylsilyl)ether (0.40 g, 80%).
  • 65
  • [ 591-20-8 ]
  • [ 72345-23-4 ]
  • [ 827310-80-5 ]
YieldReaction ConditionsOperation in experiment
87.5% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 35℃; for 1h; sonication;
  • 66
  • (2,8,13,17-tetraethyl-3,7,12,18-tetramethyl-5-oxoniaporphirinato)zinc(II) chloride [ No CAS ]
  • [ 72345-23-4 ]
  • 19,19'-((2S,4S)-2,4-pentylenedioxy)bis(3,8,12,17-tetraethyl-1,21-dihydro-2,7,13,18-tetramethyl-2H-bilin-1-one) [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With sodium hydride In tetrahydrofuran at 20℃; for 24h;
  • 67
  • [ 34737-89-8 ]
  • [ 72345-23-4 ]
  • [ 1116118-46-7 ]
  • [ 1117776-76-7 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid In benzene Heating / reflux; 1A; 1B To a solution of l-benzyl-3-methylpiperidin-4-one (Acros, 62.09 g, 305.4 mmol) and (2S,4S)- pentane-2,4-diol (TCI-US, 34.06 g, 327.0 mmol) in benzene (800 mL) was added p-toluenesulfonic acid mono hydrate (69.72 g, 404.9 mmol). The flask was fitted with a Dean-Stark trap and heated to reflux. The reaction mixture was cooled after 16 hours of reflux, concentrated to a total volume of about 500 mL and transferred to an Erlenmeyer flask with ethyl acetate. A sodium bicarbonate solution (500 mL) added with stirring and the mixture was further neutralized with solid Na2CO3 (35 g). The layers were partitioned, the organic phase washed with sodium bicarbonate, dried (Na2SO4) and concentrated to yield approximately 95 g of crude material. The residue was purified in 15 g batches by silica gel chromatography (Analogix SF-65-600 g; 35 micron silica; elution with 10% ethyl acetate-hexane) at 50 mL/min to provide 42.33 g of the first eluting isomer, (2S,4S,7R)-9- benzyl-2,4,7-trimethyl-l,5-dioxa-9-azaspiro[5.5]undecane. 1H NMR (300 MHz, DMSO-d6) δ 7.33- 7.19 (m, 5H), 4.07-3.86 (m, 2H), 3.40 (ABq, 2H, JAB = 13.5 Hz, 8VAB = 23.3 Hz), 2.41-2.20 (m, 4H), 1.90-1.76 (m, 2H), 1.59-1.47 (m, 3H), 1.12 (d, 3H, J = 6.4 Hz), 1.11 (d, 3H, J = 6.4 Hz), 0.90 (d, 3H, J = 7.1 Hz); MS (DCIZNH3) mZe 290 (M+H)+.
  • 68
  • [ 72345-23-4 ]
  • [ 65236-83-1 ]
  • [ 1126292-28-1 ]
YieldReaction ConditionsOperation in experiment
80% With N-iodo-succinimide; trifluorormethanesulfonic acid In dichloromethane at 0℃; for 0.05h; Inert atmosphere; Molecular sieve;
  • 69
  • [ 911297-75-1 ]
  • [ 72345-23-4 ]
  • (Sa)-6,6'-[(2R,4R)-2,4-dimethyl-1,5-dioxapent-1,5-diyl]-2,2'-dibromo-[1,1']biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; Sonication;
  • 70
  • [ 197243-48-4 ]
  • [ 72345-23-4 ]
  • [ 1192675-27-6 ]
YieldReaction ConditionsOperation in experiment
91% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran Inert atmosphere;
86% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;
78.2% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 4h; Sonication;
78.2% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 35℃; Sonication;

  • 71
  • [ 72345-23-4 ]
  • 1,1'-dicyano-3,3',4',4-tetramethyl-5,5'-diphenyl-2,2'-biphosphole [ No CAS ]
  • [ 1190594-35-4 ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: (2S,4S)-pentane-2,4-diol With n-butyllithium In tetrahydrofuran; hexane at -40 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,1'-dicyano-3,3',4',4-tetramethyl-5,5'-diphenyl-2,2'-biphosphole In tetrahydrofuran; hexane at -40 - 20℃; for 16h; Inert atmosphere;
  • 72
  • [ 111-88-6 ]
  • [ 72345-23-4 ]
  • [ 1225478-23-8 ]
  • [ 1225478-25-0 ]
YieldReaction ConditionsOperation in experiment
1: 52% 2: 15% With 4-Phenyl-2-butanone; 2,4-dinitrobenzenesulfonic acid In benzene for 2h; Reflux;
  • 73
  • [ 72345-23-4 ]
  • [ 58497-26-0 ]
  • [ 1227078-51-4 ]
YieldReaction ConditionsOperation in experiment
8% With pyridinium p-toluenesulfonate In benzene for 34h; Reflux;
  • 74
  • [ 696-63-9 ]
  • [ 2550-26-7 ]
  • [ 72345-23-4 ]
  • [ 2344-70-9 ]
  • [ 1233849-11-0 ]
  • [ 1243579-10-3 ]
YieldReaction ConditionsOperation in experiment
1: 56% 2: 50% 3: 12% With 2,4-dinitrobenzenesulfonic acid In benzene for 2.5h; Reflux;
  • 75
  • [ 7341-17-5 ]
  • [ 2550-26-7 ]
  • [ 72345-23-4 ]
  • [ 2344-70-9 ]
  • [ 1243579-13-6 ]
  • [ 1243579-07-8 ]
YieldReaction ConditionsOperation in experiment
1: 61% 2: 55% 3: 15% With 2,4-dinitrobenzenesulfonic acid In benzene for 2.5h; Reflux;
  • 76
  • [ 111-88-6 ]
  • [ 2550-26-7 ]
  • [ 72345-23-4 ]
  • [ 2344-70-9 ]
  • [ 1225478-23-8 ]
  • [ 1225478-25-0 ]
YieldReaction ConditionsOperation in experiment
1: 62% 2: 61% 3: 24% With 2,4-dinitrobenzenesulfonic acid In benzene for 3h; Reflux;
  • 77
  • [ 1272654-92-8 ]
  • [ 72345-23-4 ]
  • [ 1272654-77-9 ]
YieldReaction ConditionsOperation in experiment
44% In toluene Reflux; Dean stark trap; Intermediate 14: methyl(3S,7S,9S)-7,9-dimethyl-2-{A/-[(methyloxy)carbonyll-L-valyl)- 6,10-dioxa-2 azaspiro [4.51decane-3-carboxylateMethyl N-[(methyloxy)carbonyl]-L-valyl-4-oxo-L-prolinate (Intermediate 13) (650mg, 2.164mmol), (2S,4S)-2,4-pentanediol (902mg, 8.66mmol) and TsOH (82mg, 0.43mmol) were heated to reflux in toluene (40ml_) with Dean Stark trap overnight. After cooled down to rt and diluted with ethyl acetate, the resulting solution was washed with NaHC03 (ss) and brine. The organic later was dried over MgS04, filtered and evaporated. The crude product was purified by column chromatography (silica gel, 0 to 50% ethyl acetate in hexane) to give methyl (3S,7S,9S)-7,9-dimethyl- 2-{N-[(methyloxy)carbonyl]-L-valyl}-6,10-dioxa-2-azaspiro[4.5]decane-3-carboxylate (Intermediate 14) (366mg, yield: 44%) as an oil. 1H NMR (400 MHz,CHLOROFORM-c ) δ ppm 5.38 - 5.51 (m, 1 H) 4.54 (t, J=8.03 Hz, 1 H) 4.25 - 4.36 (m, 1 H) 3.91 - 4.05 (m, 2 H) 3.85 (d, J=10.04 Hz, 1 H) 3.54 - 3.77 (m, 6 H) 2.46 - 2.53 (m, 1 H) 2.12 (dd, J=12.92, 7.65 Hz, 1 H) 2.00 - 2.06 (m, 1 H) 1.54 - 1.75 (m, 3 H) 1.10 - 1.25 (m, 6 H) 1.03 (d, J=6.78 Hz, 3 H) 0.84 - 0.96 (m, 3 H). ES LC-MS m/z =409.3 (M+Na)+.
With toluene-4-sulfonic acid Inert atmosphere;
  • 78
  • C18H20ClN2P [ No CAS ]
  • [ 72345-23-4 ]
  • [ 1384619-23-1 ]
YieldReaction ConditionsOperation in experiment
387 mg With triethylamine In benzene at 0 - 95℃; for 1.25h; Inert atmosphere;
  • 79
  • [ 72345-23-4 ]
  • (R)-2-benzyl-5-oxohexanal [ No CAS ]
  • C18H26O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid In chloroform-d1 for 1h;
  • 80
  • [ 72345-23-4 ]
  • (S)-2-ethyl-5-oxohexanal [ No CAS ]
  • C13H24O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid In chloroform-d1 for 1h;
  • 81
  • [ 1394046-55-9 ]
  • [ 72345-23-4 ]
  • C19H28O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid In chloroform-d1 for 1h;
  • 82
  • [ 1394046-56-0 ]
  • [ 72345-23-4 ]
  • C18H25FO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid In chloroform-d1 for 1h;
  • 83
  • [ 1394046-57-1 ]
  • [ 72345-23-4 ]
  • C19H28O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid In chloroform-d1 for 1h;
  • 84
  • [ 909900-48-7 ]
  • [ 72345-23-4 ]
  • diethyl 2-(1-oxo-3-phenylpropan-2-yl)propanedioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid In dichloromethane
Same Skeleton Products
Historical Records

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Chemical Structure| 5978-70-1

[ 5978-70-1 ]

(R)-2-Octanol

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Chemical Structure| 543-49-7

[ 543-49-7 ]

Heptan-2-ol

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Alcohols

Chemical Structure| 13074-06-1

[ 13074-06-1 ]

(2R,3S,4R,5S)-Hexane-1,2,3,4,5-pentaol

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Chemical Structure| 24621-61-2

[ 24621-61-2 ]

(S)-Butane-1,3-diol

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Chemical Structure| 123-96-6

[ 123-96-6 ]

Octan-2-ol

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Chemical Structure| 5978-70-1

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(R)-2-Octanol

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Chemical Structure| 543-49-7

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Heptan-2-ol

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