1-(2'-Deoxy-β-D-erythro-pentafuranosyl)-7-nitroindole
A
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
In methanol for 15h; Irradiation; | A 97% B 59% |
Decomposition; Irradiation; |
3,4-O-(R)-benzylidene-2-deoxy-D-erythro-ribono-1,5-lactone
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With trifluoroacetic acid In chloroform; water at 70℃; for 10h; | 96% |
With trifluoroacetic acid In chloroform Heating; |
3-O-benzyl-2-deoxy-D-ribonolactone
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 24h; | 96% |
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With rhodium hydrido (PEt3)3 complex; 1-Phenylbut-1-en-3-one In N,N-dimethyl-formamide at 40℃; for 4h; | 93% |
With bromine In water at 20℃; for 24h; Sealed tube; | 76% |
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With bromine In water at 20℃; for 120h; Inert atmosphere; | 90% |
With bromine In water for 96h; Ambient temperature; | 86% |
With bromine In water at 20℃; for 120h; Sealed tube; | 75% |
3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-trimethylsilanyloxy-propionic acid ethyl ester
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With trifluoroacetic acid In tetrahydrofuran | 90% |
2-Deoxy-D-ribose
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With bromine In water at 25℃; for 120h; | 88% |
With bromine In water at 20℃; for 120h; | 78% |
With bromine; potassium carbonate In water at 20℃; for 8h; | 70% |
With bromine In water at 20℃; for 120h; Sealed tube; | |
With bromine In water at 20℃; for 120h; Sealed tube; |
Ethyl (4''R)-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypropionate
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With water; trifluoroacetic acid | 87% |
(-)-(S)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxypropanoic acid methyl ester
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With trifluoroacetic acid In water for 2h; Ambient temperature; | 83.1% |
With trifluoroacetic acid In water | |
With trifluoroacetic acid In water | |
With trifluoroacetic acid In water for 2h; Ambient temperature; | |
With water; trifluoroacetic acid In tetrahydrofuran at 20℃; for 4h; |
3-O-p-Nitrophenyl-D-glucose
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With 3-ethyl-4,5-dimethylthiazol-3-ium bromide; potassium carbonate; benzalacetophenone In acetonitrile at 130℃; for 0.25h; Microwave irradiation; | 53% |
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With chloro-trimethyl-silane at 20℃; for 4h; | 26% |
2,3-O-isopropylidene-D-ribofuranose
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With 2-mesityl-2,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]triazolium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 50℃; for 16h; | 13% |
2'-Deoxyguanosine
A
2,4-diamino-6-hydroxy-5-formylaminopyrimidine
B
9-(2-deoxy-β-D-erythropentopyranosyl)-2,4-diamino-5-formamidopyrimid-6-one
C
9-(2-deoxy-α-D-erythropentopyranosyl)-2,4-diamino-5-formamidopyrimid-6-one
D
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With Nitrogen dioxide In water Irradiation; Further byproducts given; | A 2.8% B 3.1% C 7.9% D 2.1% |
2'-Deoxyguanosine
A
2-amino-1,9-dihydro-6H-purin-6-one
B
2,4-diamino-6-hydroxy-5-formylaminopyrimidine
C
(2S,3S,5R)-5-(2-amino-6-oxo-1H-purin-9(6H)-yl)-3-hydroxytetrahydrofuran-2-carbaldehyde
D
9-(2-deoxy-β-D-erythropentopyranosyl)-2,4-diamino-5-formamidopyrimid-6-one
E
9-(2-deoxy-α-D-erythropentopyranosyl)-2,4-diamino-5-formamidopyrimid-6-one
F
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With Nitrogen dioxide In water Mechanism; Irradiation; gamma radio lysis; | A n/a B 2.8% C 2.2% D 3.1% E 7.9% F 2.1% G n/a |
D-Glucose
L-Lysine hydrochloride
A
2-furanoic acid
B
5-hydroxymethyl-furan-2-carboxylic acid
F
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
In water for 30h; Product distribution; Heating; pH 4.5; |
2-Bromo-2-deoxy-D-arabinono-γ-lactone
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With hydrogen; triethylamine; palladium on activated charcoal In ethyl acetate Yield given; |
(S)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-N,N-dimethyl-propionamide
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With trifluoroacetic acid In water 1) 90 deg C, 2 h 2) benzene, heating; Yield given; |
(S)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-N,N-diethyl-3-hydroxy-propionamide
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With trifluoroacetic acid In water 1) 90 deg C, 2 h 2) benzene, heating; Yield given; |
(S)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-N-methoxy-N-methyl-3-trimethylsilanyloxy-propionamide
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With trifluoroacetic acid for 2h; Heating; |
tert-butyl (4R)-4,5-O-isopropylidene-3,4,5-trihydroxypentanoate
A
(4R,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one
B
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With trifluoroacetic acid at 90 - 95℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
3,5-O-Benzylidene-2-deoxy-D-ribonic Acid γ-Lactone
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
In chloroform; water; trifluoroacetic acid at 70℃; for 10h; |
methyl (3S,4R)-3-(tert-butyldimethylsiloxy)-4,5-(isopropylidenedioxy)pentanoate
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With trifluoroacetic acid for 3h; Ambient temperature; Yield given; |
2-deoxy-D-lyxonic acid
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
at 90℃; for 2h; Yield given; |
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With hydrogen; nickel; triethylamine In methanol for 3h; |
1-(2-deoxy-2-iodo-β-D-ribofuranosyl)uracil
A
2,2'-Anhydrouridine
B
(5S)-5-(hydroxymethyl)-5H-furan-2-one
F
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
In water-d2 for 4h; Product distribution; Mechanism; Irradiation; var. solvents, in the presence of O2, also <1'-D>-2'α-iodo-2'-deoxyuridine, other deoxyoligonucleotides; | A 2.0 % Spectr. B 2.0 % Spectr. C 1.0 % Spectr. D 4.0 % Spectr. E 13 % Spectr. F 1.0 % Spectr. |
1,6-anhydro-2,3-dideoxy-β-D-erythro-hexopyranos-2-ulose
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With hydrogenchloride; peracetic acid; dimethylsulfide; acetic acid Yield given. Multistep reaction; |
1-[(2S,4S,5R)-2-(2,2-Dimethyl-propionyl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With air; water for 6h; Ambient temperature; Irradiation; |
2'-Deoxyguanosine
B
9-(2-deoxy-α-D-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one
C
2-amino-1,9-dihydro-6H-purin-6-one
D
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
at 20℃; Decomposition; Radiolysis; Further byproducts given; |
2'-deoxyuridin-1'-yl radical
A
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With tetranitromethane; oxygen In water at 20℃; Rate constant; |
2'-Deoxycytidine
A
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With menadione; water; oxygen at 10℃; Irradiation; Further byproducts given; | A 9 mg B 8 mg C 6 mg D 2 mg |
tert-butyldimethylsilyl nitrate
2-deoxy-D-ribonolactone
3,5-di-O-(tert-butyldimethylsilyl)-2-deoxy-D-ribono-1,4-lactone
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran for 8h; | 99% |
triisopropylsilyl chloride
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With 1H-imidazole; dmap In acetonitrile at 20℃; | 98% |
With 1H-imidazole; dmap In ethyl acetate; toluene; acetonitrile | 98% |
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 40℃; for 41h; | 94% |
tert-butyldimethylsilyl chloride
2-deoxy-D-ribonolactone
3,5-di-O-(tert-butyldimethylsilyl)-2-deoxy-D-ribono-1,4-lactone
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane Ambient temperature; | 97.8% |
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; | 96% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; | 80% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; zinc In tetrahydrofuran at 20℃; for 4h; Barbier Coupling Reaction; | 86% |
tert-butylchlorodiphenylsilane
2-deoxy-D-ribonolactone
2-deoxy-3,5-di-O-(tert-butyldiphenylsilyl)-D-ribonolactone
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; | 85% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; | 83% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; | 83% |
With 1H-imidazole In N,N-dimethyl-formamide for 18h; Ambient temperature; | |
With 1H-imidazole In N,N-dimethyl-formamide for 12h; |
2-deoxy-D-ribonolactone
2-Deoxy-D-ribitol
Conditions | Yield |
---|---|
With hydrogen; Rh/C In water at 130℃; under 60006 Torr; | 85% |
trityl chloride
2-deoxy-D-ribonolactone
5-O-trityl-2-deoxy-D-erythro-pentono-1,5-lactone
Conditions | Yield |
---|---|
In pyridine for 4h; Ambient temperature; | 84% |
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With bis-(1,2-dimethylpropyl)borane for 24h; Ambient temperature; | 79% |
With bis-(1,2-dimethylpropyl)borane In tetrahydrofuran for 22h; Ambient temperature; | |
With bis-(1,2-dimethylpropyl)borane In tetrahydrofuran | |
With sodium tetrahydroborate In acetic acid Yield given; | |
Multi-step reaction with 3 steps 1: imidazole / dimethylformamide / 3 h / Ambient temperature 2: 90.4 percent / DIBAL / toluene / 0.25 h / -78 °C 3: 62 percent / AcOH / tetrahydrofuran; H2O / 24 h / 60 - 70 °C View Scheme |
tetradecanoyl chloride
2-deoxy-D-ribonolactone
5-O-tetradecanoyl-2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With pyridine for 12h; Ambient temperature; | 78% |
tert-butylchlorodiphenylsilane
2-deoxy-D-ribonolactone
(4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxydihydrofuran-2(3H)-one
Conditions | Yield |
---|---|
With pyridine for 12h; Ambient temperature; | 78% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h; chemoselective reaction; | 5.1 g |
4,4'-dimethoxytrityl chloride
2-deoxy-D-ribonolactone
5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With pyridine at 20℃; for 4h; | 78% |
O-benzyl 2,2,2-trichloroacetimidate
2-deoxy-D-ribonolactone
3O,5O-dibenzyl-2-deoxy-1,4-ribonolactone
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In 1,4-dioxane pH 3; | 74% |
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane
2-deoxy-D-ribonolactone
(6aR,9aS)-2,2,4,4-tetraisopropyltetrahydro-8H-furo[3,2-f ][1,3,5,2,4]trioxadisilocin-8-one
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 25℃; Schlenk technique; Inert atmosphere; | 73% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; | 72% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 28% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; | |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; | 2.42 g |
tert-butyldimethylsilyl chloride
2-deoxy-D-ribonolactone
5-tert-butyldimethylsilyl ether of (4S,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one
Conditions | Yield |
---|---|
With pyridine; silver nitrate In acetonitrile | 70% |
With 1H-imidazole In N,N-dimethyl-formamide; acetonitrile for 16h; | 65% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Cooling with ice; | 58% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 8h; | 56.4% |
2-deoxy-D-ribonolactone
2,5-dideoxy-5-iodo-D-ribonic acid-γ-lactone
Conditions | Yield |
---|---|
With 1H-imidazole; carbon tetraiodide; triphenylphosphine In dichloromethane at 20℃; for 12h; Iodination; | 67% |
With 1H-imidazole; carbon tetraiodide; triphenylphosphine In dichloromethane |
p-toluenesulfonyl chloride
2-deoxy-D-ribonolactone
(2S,3R)-(3-hydroxy-5-oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
In pyridine at -5℃; for 6h; | 57% |
Stage #1: 2-deoxy-D-ribonolactone With pyridine at -15℃; Stage #2: p-toluenesulfonyl chloride at -15 - 0℃; for 7h; | 54% |
acetic anhydride
2-deoxy-D-ribonolactone
(-)-(4S,5R)-4-acetoxy-5-acetoxymethyl-4,5-dihydrofuran-2(3H)-one
Conditions | Yield |
---|---|
With pyridine; dmap | 55% |
With 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate In pyridine Ambient temperature; overnight; | |
With pyridine at 20℃; for 24h; Inert atmosphere; | 166 mg |
benzaldehyde
2-deoxy-D-ribonolactone
A
3,4-O-(R)-benzylidene-2-deoxy-D-erythro-ribono-1,5-lactone
Conditions | Yield |
---|---|
With hydrogenchloride for 20h; Ambient temperature; | A 52% B 8% |
With hydrogenchloride for 20h; Ambient temperature; | A 52% B 8% |
benzoyl chloride
2-deoxy-D-ribonolactone
Conditions | Yield |
---|---|
With pyridine | 43% |
acetone
2-deoxy-D-ribonolactone
3,4-O-isopropylidene-2-deoxy-D-ribono-1,5-lactone
Conditions | Yield |
---|---|
With hydrogenchloride for 20h; Ambient temperature; | 36% |
The CAS register number of D-(+)-Ribonic acid-gamma-lactone is 34371-14-7. It also can be called as D-erythro-Pentonicacid, 2-deoxy-, g-lactone and the IUPAC name about this chemical is (4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-one.
Physical properties about D-(+)-Ribonic acid-gamma-lactone are: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 1; (4)ACD/KOC (pH 7.4): 1; (5)#H bond acceptors: 4; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 3; (8)Polar Surface Area: 66.76Å2; (9)Index of Refraction: 1.522; (10)Molar Refractivity: 28.002 cm3; (11)Molar Volume: 91.815 cm3; (12)Polarizability: 11.101x10-24cm3; (13)Surface Tension: 60.509 dyne/cm; (14)Flash Point: 179.1 °C; (15)Enthalpy of Vaporization: 74.617 kJ/mol.
You can still convert the following datas into molecular structure:
(1)SMILES: C1[C@@H]([C@H](OC1=O)CO)O
(2)InChI: InChI=1/C5H8O4/c6-2-4-3(7)1-5(8)9-4/h3-4,6-7H,1-2H2/t3-,4+/m0/s1
(3)InChIKey: YIXDEYPPAGPYDP-IUYQGCFVBX
(4)Std. InChI: InChI=1S/C5H8O4/c6-2-4-3(7)1-5(8)9-4/h3-4,6-7H,1-2H2/t3-,4+/m0/s1
(5)Std. InChIKey: YIXDEYPPAGPYDP-IUYQGCFVSA-N
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