Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; carbonic acid dimethyl ester In methanol at 90℃; for 24h; Time; | 92% |
With hydrogenchloride In water for 60h; Heating; | 72% |
With cation-exchange resin In 1,4-dioxane; ethyl acetate at 78 - 84℃; for 24h; Heating; | 35% |
Conditions | Yield |
---|---|
With Hβ zeolite at 139.84℃; for 3h; | A 63% B 12% |
D-sorbitol
carbonic acid dimethyl ester
A
1,4:3,6-dianhydro-D-mannitol
B
1,4:3,6-dianhydro-L-iditol
C
isosorbide dimethyl ether
Conditions | Yield |
---|---|
With triethylamine In biphenyl at 90 - 200℃; under 63756.4 Torr; for 48h; Reagent/catalyst; Autoclave; Inert atmosphere; | A 14% B 26% C 60% |
mannitol
A
1,4:3,6-dianhydro-D-mannitol
B
1,4-anhydro-D-mannitol
C
2,5-anhydro-D-glucitol
Conditions | Yield |
---|---|
With sulfuric acid at 139.84℃; for 1h; Reagent/catalyst; | A 28% B 11% C 52% |
With hydrogen fluoride; sodium methylate; acetic acid 1) 45 h, 20 deg C; Yield given. Multistep reaction; | |
With formic acid; hydrogen fluoride; water 1) 8 min, 20 deg C; Yield given. Multistep reaction; | |
With hydrogen fluoride; sodium methylate; acetic acid Product distribution; Mechanism; multistep reaction; effect of concentration and time, intermediate acyloxonium ions monitored by 13C-NMR; | |
With formic acid; hydrogen fluoride; water Product distribution; Mechanism; multistep reaction; effect of concentration and time, intermediate acyloxonium ions monitored by 13C-NMR; |
mannitol
A
1,4:3,6-dianhydro-D-mannitol
B
1,4-anhydro-D-mannitol
C
1,5-anhydro-D-mannitol
D
2,5-anhydro-D-glucitol
Conditions | Yield |
---|---|
In water at 249.84℃; for 36h; Kinetics; Temperature; Time; | A n/a B 25% C 6% D 41% |
With sulfuric acid In water at 104℃; Product distribution; Rate constant; reaction time dependence; |
mannitol
A
1,4:3,6-dianhydro-D-mannitol
B
1,4-anhydro-D-mannitol
C
2,5-anhydro-D-mannitol
Conditions | Yield |
---|---|
In water at 276.84℃; for 10h; Kinetics; Temperature; | A n/a B n/a C 40.5% |
mannitol
ethyl acetate
A
(3R,6R)-6-hydroxyhexahydrofuro[3,2 b]furan-3-yl acetate
B
1,4:3,6-dianhydro-D-mannitol
Conditions | Yield |
---|---|
With calcium sulfate In 1,4-dioxane at 78 - 84℃; for 120h; Heating; | A 11% B n/a |
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
at 180℃; unter vermindertem Druck; |
tetrachloromethane
mannitol
toluene-4-sulfonic acid
1,4:3,6-dianhydro-D-mannitol
Conditions | Yield |
---|---|
at 140℃; |
Conditions | Yield |
---|---|
With sulfuric acid unter vermindertem Druck; |
1,4:3,6-dianhydro-2,5-di-O-benzoyl-D-mannitol
1,4:3,6-dianhydro-D-mannitol
Conditions | Yield |
---|---|
With methanol; ammonia |
methanol
sodium methylate
(3R,3aS,6R,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(4-methylbenzenesulfonate)
1,4:3,6-dianhydro-D-mannitol
mannitol
A
1,4:3,6-dianhydro-D-mannitol
B
1,4-anhydro-D-mannitol
C
1,5-anhydro-D-mannitol
D
2,5-anhydro-D-mannitol
Conditions | Yield |
---|---|
With pyridine hydrochloride at 140℃; Product distribution; |
(3R,3aS,6R,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(4-methylbenzenesulfonate)
1,4:3,6-dianhydro-D-mannitol
diethyl ether
(3R,3aS,6R,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(4-methylbenzenesulfonate)
1,4:3,6-dianhydro-D-mannitol
ammonia
(3R,3aS,6R,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(4-methylbenzenesulfonate)
1,4:3,6-dianhydro-D-mannitol
hydrogenchloride
mannitol
1,3-Dichloro-2-propanol
1,4:3,6-dianhydro-D-mannitol
Conditions | Yield |
---|---|
at 140℃; |
tetrachloromethane
mannitol
sulfuric acid
1,4:3,6-dianhydro-D-mannitol
Conditions | Yield |
---|---|
at 140℃; |
mannitol
A
3,6-anhydro-D-altritol
B
1,4:3,6-dianhydro-D-mannitol
C
1,4-anhydro-D-mannitol
D
2,5-anhydro-D-glucitol
Conditions | Yield |
---|---|
With 3 A molecular sieve at 260℃; for 2h; Product distribution; Further Variations:; Temperatures; reaction time; |
mannitol
2-Methoxypropene
A
2,5-anhydro-1,3-O-isopropylidene-D-glucitol
B
1,4:3,6-dianhydro-D-mannitol
Conditions | Yield |
---|---|
Stage #1: mannitol With hydrogenchloride for 48h; Heating; Stage #2: 2-Methoxypropene In acetone Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid 2: sulfuric acid / unter vermindertem Druck View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Hydrogenation 2: concentrated aqueous hydrochloric acid View Scheme | |
Multi-step reaction with 2 steps 1: Hydrogenation 2: aqueous HCl View Scheme |
Isosorbide
A
1,4:3,6-dianhydro-D-mannitol
B
1,4:3,6-dianhydro-L-iditol
Conditions | Yield |
---|---|
With Raney nickel | |
With Raney nickel | |
With 5% active carbon-supported ruthenium; hydrogen In water at 220℃; under 35253.5 Torr; for 3h; Catalytic behavior; Concentration; pH-value; Pressure; Reagent/catalyst; Temperature; Time; | A 5 %Spectr. B 60 %Spectr. |
Conditions | Yield |
---|---|
With hydrogen; sodium hydroxide In water at 180℃; under 87758.8 Torr; for 3h; Temperature; |
Conditions | Yield |
---|---|
In water at 20℃; for 6h; Reagent/catalyst; UV-irradiation; | A 10 %Chromat. B 87 %Chromat. |
2-(2-bromoethoxy)tetrahydropyran
1,4:3,6-dianhydro-D-mannitol
2,5-di-O-<2'-(tetrahydropyran-2-yloxy)ethoxy>-1,4:3,6-dianhydro-D-mannitol
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide 1.) 50 deg C, 15 min, 2.) 50 deg C, 1 h, 3.) 70 deg C, 12 h; | 100% |
With sodium hydride In dimethyl sulfoxide 1.) 60 deg C, 12 h; | 100% |
1,4:3,6-dianhydro-D-mannitol
1,4:3,6-dianhydro-2,5-dideoxy-2,5-dibromo-L-iditol
Conditions | Yield |
---|---|
With 1H-imidazole; bromine; triphenylphosphine In acetonitrile for 72h; Heating; | 100% |
With 1H-imidazole; bromine; triphenylphosphine In acetonitrile for 48h; Heating; | 83% |
trifluoromethylsulfonic anhydride
1,4:3,6-dianhydro-D-mannitol
[(3R,3aS,6R,6aS)-6-(trifluoromethylsulfonyloxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]trifluoromethanesulfonate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; | 100% |
With pyridine In dichloromethane at 0 - 20℃; for 3h; | 99% |
With pyridine In dichloromethane at -10 - 0℃; for 2h; | 95% |
6-chloro-dibenzo[d,f][1,3,2]-dioxaphosphepin
1,4:3,6-dianhydro-D-mannitol
C30H24O8P2
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 3h; Ambient temperature; | 99% |
3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl phosphorochloridite
1,4:3,6-dianhydro-D-mannitol
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 3h; Ambient temperature; | 99% |
p-toluenesulfonyl chloride
1,4:3,6-dianhydro-D-mannitol
(3R,3aS,6R,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(4-methylbenzenesulfonate)
Conditions | Yield |
---|---|
96% | |
With pyridine at 0℃; for 3h; Inert atmosphere; | 92% |
With triethylamine In dichloromethane at 20 - 50℃; | 91.5% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 3h; Ambient temperature; | 96% |
propargyl bromide
1,4:3,6-dianhydro-D-mannitol
1,4:3,6-dianhydro-2,5-di-O-propargyl-D-mannitol
Conditions | Yield |
---|---|
Stage #1: 1,4:3,6-dianhydro-D-mannitol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Inert atmosphere; Stage #2: propargyl bromide With 18-crown-6 ether In N,N-dimethyl-formamide; toluene; mineral oil at 20℃; for 2h; Inert atmosphere; | 96% |
Stage #1: 1,4:3,6-dianhydro-D-mannitol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: propargyl bromide With tetrabutylammomium bromide In N,N-dimethyl-formamide Inert atmosphere; | 82% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 2h; Yields of byproduct given; | A 95% B n/a |
allyl bromide
1,4:3,6-dianhydro-D-mannitol
(3R,3aR,6R,6aR)-3,6-bis(allyloxy)hexahydrofuro[3,2-b]furan
Conditions | Yield |
---|---|
With potassium tert-butylate In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 94% |
With sodium hydroxide | |
With sodium hydroxide; acetone | |
With 1,4-dioxane; sodium hydroxide |
1,4:3,6-dianhydro-D-mannitol
(3S,3aS,6S,6aS)-3,6-dichlorohexahydrofuro[3,2-b]furan
Conditions | Yield |
---|---|
With pyridine; thionyl chloride at 0 - 70℃; for 20h; | 94% |
With pyridine; thionyl chloride |
Conditions | Yield |
---|---|
With palladium diacetate; triphenylphosphine; benzoic acid In 1,4-dioxane at 90℃; under 30003 Torr; for 20h; | 94% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -10 - 20℃; for 4h; | 93% |
Conditions | Yield |
---|---|
Stage #1: 1,4:3,6-dianhydro-D-mannitol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: bromopentene In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere; | 91% |
2-Bromoethyl ethyl ether
1,4:3,6-dianhydro-D-mannitol
(3R,3aR,6R,6aR)-3,6-Bis-(2-ethoxy-ethoxy)-hexahydro-furo[3,2-b]furan
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide 1.) 50 deg C, 15 min, 2.) 50 deg C, 1 h, 3.) 70 deg C, 12 h; | 90% |
With sodium hydroxide In dimethyl sulfoxide 1.) 60 deg C, 12 h; | 90% |
Bromoacetaldehyde diethyl acetal
1,4:3,6-dianhydro-D-mannitol
(3R,3aR,6R,6aR)-3,6-Bis-(2,2-diethoxy-ethoxy)-hexahydro-furo[3,2-b]furan
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide 1.) 50 deg C, 15 min, 2.) 50 deg C, 1 h, 3.) 70 deg C, 12 h; | 90% |
Bromoacetaldehyde diethyl acetal
1,4:3,6-dianhydro-D-mannitol
A
(3R,3aR,6R,6aR)-3,6-Bis-(2,2-diethoxy-ethoxy)-hexahydro-furo[3,2-b]furan
B
(3R,3aR,6R,6aR)-6-(2,2-Diethoxy-ethoxy)-hexahydro-furo[3,2-b]furan-3-ol
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide 1.) 60 deg C, 12 h; | A 90% B 8% |
With sodium hydride In dimethyl sulfoxide 1.) 50 deg C, 2 h, 2.) 70 deg C, 12 h; | A 29% B 20% |
benzoic acid
1,4:3,6-dianhydro-D-mannitol
(3S,3aR,6S,6aR)-6-(benzoyloxy)hexahydrofuro[3,2-b]furan-3-yl benzoate
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 25℃; for 21h; Mitsunobu reaction; | 90% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 21h; | 88% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; | |
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃; | |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 12h; |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 3h; Ambient temperature; | 89% |
1,4:3,6-dianhydro-D-mannitol
Methacryloyl chloride
isomannide bis-methacrylate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 24h; | 89% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 3h; Ambient temperature; | 87% |
Conditions | Yield |
---|---|
Stage #1: pyrocatechol phosphorochloridite; 1,4:3,6-dianhydro-D-mannitol With triethylamine In N,N-dimethyl-formamide at 20℃; for 20h; Stage #2: With sulfur In N,N-dimethyl-formamide at 20℃; for 20h; | 87% |
1,4:3,6-dianhydro-D-mannitol
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 3h; Ambient temperature; | 86% |
Conditions | Yield |
---|---|
Stage #1: chloro-diphenylphosphine; 1,4:3,6-dianhydro-D-mannitol With triethylamine In N,N-dimethyl-formamide at 20℃; for 144h; Stage #2: With 1,3-dibromo-propane In N,N-dimethyl-formamide at 20℃; for 336h; | 86% |
Conditions | Yield |
---|---|
Stage #1: 1,4:3,6-dianhydro-D-mannitol With triethylamine; trichlorophosphate In 1,4-dioxane at 10 - 20℃; Stage #2: diethylamine In 1,4-dioxane at 20 - 75℃; for 3h; | 85% |
Conditions | Yield |
---|---|
Stage #1: 1,4:3,6-dianhydro-D-mannitol With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 2h; Stage #2: monomethyl oxalyl chloride In tetrahydrofuran at 0 - 20℃; for 48h; | 84% |
Stage #1: 1,4:3,6-dianhydro-D-mannitol With n-butyllithium In tetrahydrofuran at -78 - 30℃; for 2h; Stage #2: monomethyl oxalyl chloride In tetrahydrofuran at 0 - 30℃; for 48h; | 84% |
Quinoline-6-carboxylic acid
1,4:3,6-dianhydro-D-mannitol
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere; | 84% |
Conditions | Yield |
---|---|
Stage #1: bis(diethylamino)chlorophosphine; 1,4:3,6-dianhydro-D-mannitol With triethylamine In 1,4-dioxane at 20℃; for 18h; Stage #2: With sulfur In 1,4-dioxane at 20℃; for 4h; | A n/a B n/a C 83% |
Stage #1: bis(diethylamino)chlorophosphine; 1,4:3,6-dianhydro-D-mannitol With triethylamine In chloroform at 20℃; for 24h; Stage #2: With sulfur In chloroform at 20℃; for 4h; | |
Stage #1: bis(diethylamino)chlorophosphine; 1,4:3,6-dianhydro-D-mannitol With pyridine at 20℃; for 24h; Stage #2: With sulfur at 20℃; for 4h; |
2-ethoxyethyl p-toluenesulfonate
1,4:3,6-dianhydro-D-mannitol
(3R,3aR,6R,6aR)-3,6-Bis-(2-ethoxy-ethoxy)-hexahydro-furo[3,2-b]furan
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide 1.) 50 deg C, 15 min, 2.) 50 deg C, 1 h, 3.) 70 deg C, 12 h; | 82% |
With sodium hydroxide In dimethyl sulfoxide 1.) 60 deg C, 12 h; | 82% |
The D-Mannitol,1,4:3,6-dianhydro-, with CAS registry number 641-74-7, belongs to the following product categories: (1)Alcohols and Derivatives; (2)Heterocycles. It has the systematic name of 1,4:3,6-dianhydro-D-mannitol. And the chemical formula of this chemical is C6H10O4. When use this chemical, do not breathe dust and avoid contact with skin and eyes.
Physical properties of D-Mannitol,1,4:3,6-dianhydro-: (1)ACD/LogP: -1.19; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 3; (6)ACD/KOC (pH 7.4): 3; (7)#H bond acceptors: 4; (8)#H bond donors: 2; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 58.92 Å2; (11)Index of Refraction: 1.562; (12)Molar Refractivity: 32.114 cm3; (13)Molar Volume: 99.011 cm3; (14)Polarizability: 12.731×10-24cm3; (15)Surface Tension: 56.653 dyne/cm; (16)Enthalpy of Vaporization: 71.639 kJ/mol; (17)Vapour Pressure: 0 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: O[C@H]1[C@H]2OC[C@@H](O)[C@H]2OC1
(2)InChI: InChI=1/C6H10O4/c7-3-1-9-6-4(8)2-10-5(3)6/h3-8H,1-2H2/t3-,4-,5-,6-/m1/s1
(3)InChIKey: KLDXJTOLSGUMSJ-KVTDHHQDBJ
(4)Std. InChI: InChI=1S/C6H10O4/c7-3-1-9-6-4(8)2-10-5(3)6/h3-8H,1-2H2/t3-,4-,5-,6-/m1/s1
(5)Std. InChIKey: KLDXJTOLSGUMSJ-KVTDHHQDSA-N
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