| Identification | More | [Name]
Isomannide | [CAS]
641-74-7 | [Synonyms]
1,4:3,6-DIANHYDRO-D-MANNITOL
1,4:3,6-DIANHYDROMANNITOL
ISOMANNIDE
1,4
Perhydro-3,6-dihydroxyfuro[3,2-b]furan
3-Nitro-4-hydroxy diphenyl
Isomannide,98%
3,6-Dianhydro-D-mannitol
3-NITRO-HYDROXYDIPHENYL
1,4,3,6-Dianhydro-D-mannitolIsomannide
4,8-Dioxabicyclo[3.3.0]octane-2,6-diol
(3aα,6aα)-Hexahydrofuro[3,2-b]furan-3β,6β-diol
(3R,3aα,6aα)-Hexahydrofuro[3,2-b]furan-3β,6β-diol
2,3,3aα,5,6,6aα-Hexahydrofuro[3,2-b]furan-3β,6β-diol
D-Isomannide | [EINECS(EC#)]
211-374-1 | [Molecular Formula]
C6H10O4 | [MDL Number]
MFCD00064818 | [Molecular Weight]
146.14 | [MOL File]
641-74-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
80-85 °C (lit.) | [alpha ]
89 º (c=3, H2O) | [Boiling point ]
150 °C / 12mmHg | [density ]
1.0945 (rough estimate) | [refractive index ]
1.4128 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly), Water | [form ]
Solid | [pka]
13.17±0.40(Predicted) | [color ]
White to Off-White | [Optical Rotation]
[α]25/D +89°, c = 3 in H2O | [Water Solubility ]
almost transparency | [BRN ]
80509 | [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 | [InChIKey]
KLDXJTOLSGUMSJ-KVTDHHQDSA-N | [SMILES]
O[C@@H]1CO[C@@H]2[C@H](O)CO[C@H]12 | [CAS DataBase Reference]
641-74-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [F ]
10-21 | [HS Code ]
29329990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white powder | [Uses]
1,4:3,6-Dianhydro-D-mannitol is a reagent used in the synthesis of new isomannide-based peptidomimetic as human tissue kallikrein 1 inhibitor using Ugi multicomponent reaction. It also functions as a chiral ligand for stereoselective synthesis. | [Synthesis]
The general procedure for the synthesis of 1,4:3,6-bis-anhydromannitol from D-mannitol was as follows: 1350 g of crystalline D-mannitol was added to a reduced-pressure reactor equipped with a stirrer and heated to 170 °C to melt it. Subsequently, 10 g of 98% concentrated sulfuric acid was added to the melt, and the reaction lasted for 20 h at 170 °C and 2 kPa with nitrogen gas being passed at a flow rate of 200 mL/min. Upon completion of the reaction, the product was cooled to 90 °C and 30 g of 48% (w/w) aqueous sodium hydroxide solution was added to give crude 1,4:3,6-bis-anhydromannitol. Next, 39 g of horseshoe-based wood activated carbon (trade name: Tyco K, produced by Futamura Chemical Co., Ltd.) was added to the crude product and stirred for 3 h for decolorization to obtain a mixture to be distilled. Water was distilled from the mixture at 120 °C and 5 kPa. Subsequently, a reduced pressure distillation was carried out at 170 °C and 0.3 kPa under reduced pressure by passing nitrogen at a flow rate of 200 mL/min, resulting in 491 g of product. A portion of the distilled product was taken and the pH of the mixture was determined to be 10 according to the method of Example 1. | [References]
[1] Green Chemistry, 2015, vol. 17, # 2, p. A1176 - A1185
[2] Journal of Chemical Crystallography, 1997, vol. 27, # 3, p. 161 - 166
[3] Carbohydrate Research, 1980, vol. 79, p. 133 - 141
[4] Journal of Organometallic Chemistry, 1983, vol. 253, # 2, p. 249 - 252
[5] Journal of the American Chemical Society, 1946, vol. 68, p. 930,934 |
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