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| | 3-O-Benzyl-4-(hydroxymethyl-1,2-O-isopropylidene)-alpha-D-erythropentofuranose Basic information |
| Product Name: | 3-O-Benzyl-4-(hydroxymethyl-1,2-O-isopropylidene)-alpha-D-erythropentofuranose | | Synonyms: | ((3aR,6S,6aR);-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5,5-diyl);3-O-benzyl-4-C-(hydroxymethyl)-1,2-O-isopropylidene-a-D-ribofuranose;3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE;3-O-Benzyl-4-(hydroxymethyl)-1,2-O-isopropylidene-a-D-ribofuranose;3-O-Benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose;3-O-Benzyl-4-(hydroxyMethyl)-1,2-O-isopropylidene-alfa-D-ribofuranose;((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5,5-diyl)dimethanol | | CAS: | 63593-03-3 | | MF: | C16H22O6 | | MW: | 310.34 | | EINECS: | 613-267-9 | | Product Categories: | | | Mol File: | 63593-03-3.mol |  |
| | 3-O-Benzyl-4-(hydroxymethyl-1,2-O-isopropylidene)-alpha-D-erythropentofuranose Chemical Properties |
| Boiling point | 442.5±45.0 °C(Predicted) | | density | 1.29 | | storage temp. | 2-8°C | | pka | 13.95±0.10(Predicted) | | Appearance | White to off-white Solid | | Optical Rotation | Consistent with structure | | InChI | InChI=1/C16H22O6/c1-15(2)20-12-13(19-8-11-6-4-3-5-7-11)16(9-17,10-18)22-14(12)21-15/h3-7,12-14,17-18H,8-10H2,1-2H3/t12-,13+,14+/s3 | | InChIKey | QVXXTLFHRGMIHD-AEMUBKJBNA-N | | SMILES | [C@]12([H])OC(C)(C)O[C@@]1([H])OC(CO)(CO)[C@H]2OCC1C=CC=CC=1 |&1:0,7,15,r| |
| | 3-O-Benzyl-4-(hydroxymethyl-1,2-O-isopropylidene)-alpha-D-erythropentofuranose Usage And Synthesis |
| Chemical Properties | White powder | | Synthesis | The general procedure for the synthesis of ((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxazole-5,5-diyl)dimethanol from formaldehyde and the compound (CAS: 63593-02-2) was as follows: to a 3000 mL round-bottomed flask at room temperature was added compound 269-4 (100 g 359.32 mmol, 1.00 equiv) to a solution of tetrahydrofuran (500 mL). Water (500 mL) was then added. After the mixture was cooled to 0 °C, sodium hydroxide solution (600 mL, 2N aqueous solution) was slowly added, followed by aqueous formaldehyde solution (240 mL, 37%). The reaction mixture was stirred at room temperature overnight. After the reaction was completed, the mixture was diluted with ethyl acetate (1500 mL) and washed with saturated aqueous sodium bicarbonate solution. Finally, the mixture was washed with aqueous sodium chloride solution (3 x 500 mL). | | References | [1] Tetrahedron, 2002, vol. 58, # 26, p. 5335 - 5345
[2] Patent: US2015/366888, 2015, A1. Location in patent: Paragraph 1083; 1087
[3] Patent: US2015/366887, 2015, A1. Location in patent: Paragraph 1015; 1019
[4] Patent: US2015/105341, 2015, A1. Location in patent: Paragraph 1148 |
| | 3-O-Benzyl-4-(hydroxymethyl-1,2-O-isopropylidene)-alpha-D-erythropentofuranose Preparation Products And Raw materials |
| Raw materials | α-D-ribo-Hexofuranose, 1,2:5,6-bis-O-(1-methylethylidene)-3-O-(phenylmethyl)-, (5ξ)--->(3aR,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol:methane-->1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose-->1,2-O-ISOPROPYLIDENE-3-BENZYLOXY-D-ALLOFURANOSE-->3-o-benzyl-1,2-o-isopropylidene-a-d-ribo-pentadialdo-1,4-furanose-->3-O-Benzyl-1,2:5,6-bis-O-isopropylidene-alpha-D-galactofuranose-->Formaldehyde-->Tetrahydrofuran-->Water-->Benzyl bromide | | Preparation Products | N4-Banzoyl-5-methyl-2'-O,4'-C-methylenecytidine-->3-O-Benzyl4-C-(methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-a-D-ribofuranose-->1,2-O-(1-methylethylidene)-4-C-[(phenylmethoxy)methyl]-3-O-(phenylmethyl)-L-Lyxofuranose |
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