2,3,5-tri-O-acetyl-1-O-methyl-β-D-ribofuranose
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
With tris(2,4,6-trimethoxyphenyl)phosphine In methanol at 20℃; for 28h; | 93% |
With potassium carbonate In methanol |
Conditions | Yield |
---|---|
With sodium for 12h; Ambient temperature; | 90% |
methanol
(2R,3R,4S,5R)-2-azido-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
With sodium 1.) reflux, 3 h, 2.) RT, overnight; | 89% |
methyl 2,3,3'-tri-O-benzoyl-β-D-apiofuranoside
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
With potassium hydroxide In methanol for 0.5h; Ambient temperature; | 82% |
methanol
D-ribose
A
1-O-methyl-D-ribofuranose
B
methyl α-D-ribofuranoside
Conditions | Yield |
---|---|
With hydrogenchloride | A 70.9% B 20% |
With hydrogenchloride | |
With iodine for 7h; Product distribution; Heating; HPLC analysis (used dihydrogen sulphate form column) of product distribution in iodine-catalyzed methyl glycosidation; |
methanol
D-Ribose
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
With Dowex-50 (HCl form) at 0 - 25℃; for 72h; Inert atmosphere; | 68% |
With hydrogenchloride; water at 20℃; for 3.5h; | 63% |
With hydrogenchloride at 20℃; for 3.5h; | 63% |
With sulfuric acid | |
With sulfuric acid for 20h; Ambient temperature; |
methanol
D-Ribose
A
1-O-methyl-D-ribofuranose
B
methyl α-D-ribofuranoside
Conditions | Yield |
---|---|
With sulfuric acid at 4℃; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With sulfuric acid at 0 - 4℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With hydrogenchloride at 25℃; for 1.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
sulfuric acid at 20℃; Cooling with ice; | |
With Dowex 50Wx8 H+ form at 4℃; for 20h; | A n/a B n/a |
Conditions | Yield |
---|---|
In tetrachloromethane for 24h; Ambient temperature; Yield given; |
β-D-ribofuranose
(1R,2R,4aS,5S,8aR)-2-(2-Hydroxy-ethyl)-5-methoxymethoxy-1-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
With hydrogenchloride Ambient temperature; |
methyl 5-benzoyl-2,3-benzoxonium-α-D-xylofuranoside
A
1-O-methyl-D-ribofuranose
B
methyl α-D-ribofuranoside
Conditions | Yield |
---|---|
With sodium methylate; sodium hydrogencarbonate 2.) CH3OH; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
hydrogenchloride
methanol
methyl β-D-ribopyranoside
A
methyl α-D-ribopyranoside
B
1-O-methyl-D-ribofuranose
C
methyl α-D-ribofuranoside
Conditions | Yield |
---|---|
at 35℃; Kinetics; |
methyl 5-azido-2,3-di-O-benzoyl-5-deoxy-α-D-xylofuranoside
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: nitrosonium hexafluorophosphate / acetonitrile / 0.25 h / 0 °C 2: 1.) NaHCO3 (aq.), 2.) NaOCH3 / 2.) CH3OH View Scheme |
methyl 2,3-di-O-benzoyl-5-O-p-toluenesulfonyl-α-D-xylofuranoside
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 0.8 g / NaN3 / dimethylformamide / 6 h / 90 °C 2: nitrosonium hexafluorophosphate / acetonitrile / 0.25 h / 0 °C 3: 1.) NaHCO3 (aq.), 2.) NaOCH3 / 2.) CH3OH View Scheme |
methyl 2-O-benzoyl-α-D-xylofuranoside
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 2.) pyridine 2: 0.8 g / NaN3 / dimethylformamide / 6 h / 90 °C 3: nitrosonium hexafluorophosphate / acetonitrile / 0.25 h / 0 °C 4: 1.) NaHCO3 (aq.), 2.) NaOCH3 / 2.) CH3OH View Scheme |
1-azido-2,3,4-tri-O-acetylribose
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 86 percent / methanol, sodium / 12 h / Ambient temperature 2: 89 percent / sodium / 1.) reflux, 3 h, 2.) RT, overnight View Scheme |
1,2,3,5-tetraacetylribose
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 98 percent / trimethylsilylazide, stannic chloride / CH2Cl2 / 48 h / Ambient temperature 2: 90 percent / sodium / 12 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: 98 percent / trimethylsilylazide, stannic chloride / CH2Cl2 / 48 h / Ambient temperature 2: 86 percent / methanol, sodium / 12 h / Ambient temperature 3: 89 percent / sodium / 1.) reflux, 3 h, 2.) RT, overnight View Scheme |
di-O-benzoyl-1,2-O-(α-methoxybenzylidene)-α-D-ribofuranose
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 92 percent / HgBr2, pyridinium toluene-p-sulphonate / CH2Cl2; methanol / Heating 2: 82 percent / KOH / methanol / 0.5 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
In methanol |
(6aR,8R,9R,9aS)-2,2,4,4-tetraisopropyl-8-methoxytetrahydro-6H-furo[3,2- f][1,3,5,2,4]trioxadisilocin-9-ol
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
With tetramethylammonium fluoride; acetic acid In N,N-dimethyl-formamide at 20℃; for 2h; |
methanol
1,2,3,5-tetra-O-acetyl-D-ribofuranose
A
1-O-methyl-D-ribofuranose
B
methyl α-D-ribofuranoside
Conditions | Yield |
---|---|
Stage #1: methanol; 1,2,3,5-tetra-O-acetyl-D-ribofuranose With sodium methylate at 20℃; Stage #2: In methanol at 20℃; for 15h; pH=3; optical yield given as %de; |
Conditions | Yield |
---|---|
With Dowex-50W | |
Stage #1: methanol With acetyl chloride at 0 - 5℃; for 0.333333h; Stage #2: β-D-ribofuranose at 20℃; for 24h; Time; | 55 mg |
With sulfuric acid | |
With toluene-4-sulfonic acid at 30 - 50℃; Temperature; Reagent/catalyst; |
D-Ribose
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
Stage #1: D-Ribose With sulfuric acid In methanol for 16h; Cooling with ice; Stage #2: In methanol |
methanol
D-ribose
A
methyl β-D-ribopyranoside
B
methyl α-D-ribopyranoside
C
1-O-methyl-D-ribofuranose
D
methyl α-D-ribofuranoside
Conditions | Yield |
---|---|
With QuadraPure sulfonic acid 450-800 micron beads at 120℃; for 0.0666667h; Flow reactor; | A 56 %Spectr. B 13 %Spectr. C 20 %Spectr. D 11 %Spectr. |
Conditions | Yield |
---|---|
Acidic conditions; |
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
With 5% active carbon-supported ruthenium; hydrogen; water-d2; sodium hydroxide at 80℃; for 24h; | 100% |
1-Methoxy-4-(1-methoxy-vinyl)-benzene
1-O-methyl-D-ribofuranose
methyl 2,3-O-<(methoxyphenyl)ethylidene>-β-D-ribofuranoside
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 0.5h; Ambient temperature; | 97% |
benzoyl chloride
1-O-methyl-D-ribofuranose
methyl 2,3,3'-tri-O-benzoyl-β-D-apiofuranoside
Conditions | Yield |
---|---|
With pyridine 1.) from 0 deg C to 4 deg C, 20 h, 2.) RT, 4 h; | 96.5% |
In pyridine; chloroform at 0℃; for 0.75h; | 95% |
With pyridine Ambient temperature; | |
Stage #1: 1-O-methyl-D-ribofuranose With dmap; triethylamine In 1,2-dichloro-ethane Stage #2: benzoyl chloride In 1,2-dichloro-ethane at 30℃; Solvent; Temperature; |
chlorophosphoric acid diphenyl ester
1-O-methyl-D-ribofuranose
β-methyl-5-(diphenoxyphosphoryl)ribofuranoside
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 3h; | 96% |
Trimethyl orthoacetate
1-O-methyl-D-ribofuranose
methyl 5-O-acetyl-β-D-ribofuranoside
Conditions | Yield |
---|---|
With lanthanum chloride on silica gel In methanol | 94% |
p-Anisaldehyde dimethyl acetal
1-O-methyl-D-ribofuranose
methyl 2,3-O-p-methoxybenzylidene-β-D-ribofuranoside
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 70℃; for 4h; | 93% |
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 70℃; for 4h; | 93% |
1-O-methyl-D-ribofuranose
methyl β-D-2,3-dideoxyribofuranoside
Conditions | Yield |
---|---|
With hydrogen In 1,4-dioxane at 139.84℃; under 60006 Torr; for 24h; Autoclave; | 93% |
With hydrogen In 1,4-dioxane at 139.84℃; under 57755.8 Torr; for 8h; |
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane
1-O-methyl-D-ribofuranose
(6aR,8R,9R,9aS)-2,2,4,4-tetraisopropyl-8-methoxytetrahydro-6H-furo[3,2- f][1,3,5,2,4]trioxadisilocin-9-ol
Conditions | Yield |
---|---|
With pyridine for 2h; Ambient temperature; | 90% |
With pyridine at 0 - 20℃; for 24h; | 90% |
With pyridine at 20℃; for 1h; | 83% |
tert-butylchlorodiphenylsilane
1-O-methyl-D-ribofuranose
(2R,3S,4R,5R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-methoxytetrahydrofuran-3,4-diol
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 24h; | 90% |
With triethylamine In dichloromethane for 18h; Ambient temperature; | 54.8% |
Conditions | Yield |
---|---|
Stage #1: 1-O-methyl-D-ribofuranose With BDMDAP; dimethyltin dichloride In 1-methyl-pyrrolidin-2-one at 80℃; for 12h; Stage #2: triethylamine carbonate In 1-methyl-pyrrolidin-2-one; water regioselective reaction; | 90% |
trityl chloride
1-O-methyl-D-ribofuranose
(-)-Methyl-5-O-trityl-β-D-ribofuranosid
Conditions | Yield |
---|---|
With pyridine at 120℃; for 3h; | 87% |
With pyridine at 120℃; for 3h; tritylation; | 87% |
With pyridine; dmap for 24h; Ambient temperature; | |
With pyridine for 24h; Ambient temperature; | |
With pyridine at 120℃; for 3h; |
2,2-dimethoxy-propane
1-O-methyl-D-ribofuranose
((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid In acetone for 22h; Ambient temperature; | 87% |
With camphor-10-sulfonic acid In acetone at 25℃; for 18h; Inert atmosphere; | 73% |
With toluene-4-sulfonic acid In N,N-dimethyl-formamide for 24h; Etherification; |
4,4'-dimethoxytrityl chloride
1-O-methyl-D-ribofuranose
2-[bis(4-methoxyphenyl)phenylmethoxymethyl]-5-methoxy-tetrahydrofuran-3,4-diol
Conditions | Yield |
---|---|
With pyridine at 120℃; for 3h; | 87% |
triisopropylsilyl chloride
1-O-methyl-D-ribofuranose
(6aR,8R,9R,9aS)-2,2,4,4-tetraisopropyl-8-methoxytetrahydro-6H-furo[3,2- f][1,3,5,2,4]trioxadisilocin-9-ol
Conditions | Yield |
---|---|
In pyridine at 20℃; for 1h; | 83% |
1-O-methyl-D-ribofuranose
methyl 5-deoxy-5-iodo-β-D-ribofuranoside
Conditions | Yield |
---|---|
With 1H-imidazole; iodine; triphenylphosphine In tetrahydrofuran Heating; | 80% |
Conditions | Yield |
---|---|
With pyridine In chloroform at 20℃; for 5h; Tosylation; | 76% |
acetone
1-O-methyl-D-ribofuranose
((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol
Conditions | Yield |
---|---|
zeolite HY at 50℃; for 48h; | 75% |
With hydrogenchloride In methanol; water |
thioacetic acid
1-O-methyl-D-ribofuranose
Methyl 5-S-acetyl-5-thio-β-D-ribofuranoside
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; | 71% |
tert-butyldimethylsilyl chloride
1-O-methyl-D-ribofuranose
methyl 5-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranoside
Conditions | Yield |
---|---|
With dmap; triethylamine In N,N-dimethyl-formamide at 25℃; for 20h; Inert atmosphere; | 68% |
phenyl isocyanate
1-O-methyl-D-ribofuranose
A
methyl 2-O-(phenylcarbamoyl)-β-D-ribofuranoside
Conditions | Yield |
---|---|
With Zn naphthenate In N,N-dimethyl-formamide at -15℃; Product distribution; | A 9% B 63% |
With Zn naphthenate In N,N-dimethyl-formamide at -15℃; | A 9% B 63% |
Dibenzyl N,N-diisopropylphosphoramidite
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
Stage #1: Dibenzyl N,N-diisopropylphosphoramidite; 1-O-methyl-D-ribofuranose With 4,5-dicyano-1H-imidazole In N,N-dimethyl-formamide at -10℃; for 5h; Inert atmosphere; Stage #2: With 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl-d6-formamide at -10 - 25℃; for 0.5h; Inert atmosphere; | 60% |
1-chloromethyl-3-methyl-benzene
1-O-methyl-D-ribofuranose
methyl 2,3,5-tri-O-(3-methylbenzyl)-β-D-ribofuranoside
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide at 25℃; for 2h; | 57% |
tert-butylchlorodiphenylsilane
1-O-methyl-D-ribofuranose
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane | 54.8% |
With dmap; triethylamine In dichloromethane |
m-methoxybenzyl chloride
1-O-methyl-D-ribofuranose
methyl 2,3,5-tri-O-(3-methoxybenzyl)-β-D-ribofuranoside
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide for 2h; Ambient temperature; | 28.5% |
The CAS register number of Methyl beta-D-ribofuranoside is 7473-45-2. It also can be called as β-D-Ribofuranoside, methyl and the IUPACc name about this chemical is (2R,3S,4R,5R)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol. The molecular formula about this chemical is C6H12O5 and molecular weight is 164.16. It belongs to the following product categories which include 13C & 2H Sugars; Biochemistry; Nucleosides, Nucleotides & Related Reagents; Ribose; Riboses and 2'-Deoxyriboses; Sugars; Carbohydrates & Derivatives; Carbohydrates; Carbohydrates A to; Carbohydrates M-OBiochemicals and Reagents; Monosaccharide and so on.
Physical properties about Methyl beta-D-ribofuranoside are: (1)ACD/LogP: -0.83; (2)ACD/LogD (pH 5.5): -0.83; (3)ACD/LogD (pH 7.4): -0.83; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 8.38; (7)ACD/KOC (pH 7.4): 8.38; (8)#H bond acceptors: 5; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 46.15Å2; (12)Index of Refraction: 1.522; (13)Molar Refractivity: 35.77 cm3; (14)Molar Volume: 117.2 cm3; (15)Polarizability: 14.18x10-24cm3; (16)Surface Tension: 58.4 dyne/cm; (17)Enthalpy of Vaporization: 68.68 kJ/mol; (18)Boiling Point: 348.7 °C at 760 mmHg; (19)Vapour Pressure: 3.01E-06 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: O[C@@H]1[C@H](O[C@@H](OC)[C@@H]1O)CO
(2)InChI: InChI=1/C6H12O5/c1-10-6-5(9)4(8)3(2-7)11-6/h3-9H,2H2,1H3/t3-,4-,5-,6-/m1/s1
(3)InChIKey: NALRCAPFICWVAQ-KVTDHHQDBI
(4)Std. InChI: InChI=1S/C6H12O5/c1-10-6-5(9)4(8)3(2-7)11-6/h3-9H,2H2,1H3/t3-,4-,5-,6-/m1/s1
(5)Std. InChIKey: NALRCAPFICWVAQ-KVTDHHQDSA-N
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