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| Type | HazMat fee for 500 gram (Estimated) |
| Excepted Quantity | USD 0.00 |
| Limited Quantity | USD 15-60 |
| Inaccessible (Haz class 6.1), Domestic | USD 80+ |
| Inaccessible (Haz class 6.1), International | USD 150+ |
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| Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
*Storage: {[sel_prStorage]}
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
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| CAS No. : | 27908-36-7 |
| Formula : | C13H20N3O9P |
| M.W : | 393.29 |
| SMILES Code : | OP(N1CCOCC1)(OC[C@@H]2[C@@H](O)[C@@H](O)[C@]([H])(N3C=CC(NC3=O)=O)O2)=O |
| English Name : | ((2R,3S,4R,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl hydrogen morpholinophosphonate |
| MDL No. : | N/A |
| GHS Pictogram: | |
| Signal Word: | |
| Hazard Statements: | |
| Precautionary Statements: | |
| Class: | |
| UN#: | |
| Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 52% 2: 50% | Stage #1: 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol With hydrogenchloride In benzene at 20℃; for 0.5h; Stage #2: tetra-n-butylammonium dihydrogen phosphate With triethylamine In acetonitrile at 20℃; for 3h; Inert atmosphere; Molecular sieve; Stage #3: uridine 5'-monophosphate morpholidate Further stages; | 1; 2; 3; 4; 5 Embodiment 1 first step synthesis general method General procedure: In a 25 mL round-bottomed flask, 1 g of acetylated glycal 1 was repeatedly dissolved in an appropriate amount of benzene for 3 times by rotary evaporation, and finally dissolved in 12 mL of benzene, and dried HCl (g) was poured into the reaction solution and stirred at room temperature. Reaction for 30min, TLC detects the reaction progress (petroleum ether: ethyl acetate=1:1), after the alkenose reaction is complete, HCl (g) and benzene are removed by distillation under reduced pressure to obtain a pale yellow syrupy mixture 2, which can be directly carried out next reaction. Embodiment 2 second step synthesis general method In a 50 mL round-bottomed flask, the mixture of 2 obtained above was dissolved in 25 mL of anhydrous CH3CN, the pH of the solution was adjusted to ≈ 9 with Et3N, the molecular sieves activated at high temperature were added, and the mixture was cooled in an ice-water bath. Dissolve 1.5g Bu4NH2PO4 in 12mL anhydrous CH3CN, under the protection of N2, add the Bu4NH2PO4 solution dropwise to the above 2 mixture, and the mixture reacts at room temperature for about 3h. The progress of the reaction was detected by TLC (with CH2Cl2:CH3OH:H2O:Et3N=16:8:0.2:0.3),After the reaction, the residual liquid was subjected to silica gel column chromatography with the system of CH2Cl2/CH3OH/H2O/Et3N=24/6/0.2/0.3 as eluent to obtain acetylated 2-deoxysugar-phosphate tetrabutylammonium salt 3. Embodiment 3 Synthesis general method of the third stepDissolve 0.05g of acetylated 2-deoxysugar-1-phosphate tetrabutylammonium salt 3 in a 25mL pear-shaped bottle, dissolve it with a small amount of anhydrous pyridine and rotate it, repeat 3 times, add 0.05g of UMP-morpholidate, and then add 0.01 g of UMP-morpholidate g tetrazole, finally added 0.5mL anhydrous pyridine as the reaction solvent, the whole reaction system was reacted under the protection of N2 gas for 48h, the reaction was detected by TLC, and the developing solvent was CHCl3:CH3OH:25%NH4OH:H2O=3.5:2:0.2:0.2 After the reaction, pyridine was evaporated, and pure uridine diphosphate acetylated-2-deoxysugar 4 was obtained by silica gel column chromatography (gradient elution with CHCl3:CH3OH:25% NH4OH:H2O system). The fourth step of embodiment 4 synthesis general method40.02g of uridine diphosphate acetylated-2-deoxysugar was dissolved in 2mL of CH3OH/H2O/Et3N (7/3/1) mixed solvent, reacted for 3h under stirring at room temperature, and the reaction progress was detected by TLC (with CHCl3:CH3OH: 25% NH4OH:H2O=1:1:0.2:0.2 system as a developing solvent), after the reaction, spin dry the solvent, and obtain uridine diphosphate 2-deoxysugar 5 in the form of triethylammonium salt by silica gel column chromatography . The acetyl group can also be removed by continuous reaction for 48 hours in a 25% NH4OH/H2O (1/5) solution system at 4°C. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Stage #1: 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol With hydrogenchloride In benzene at 20℃; for 0.5h; Stage #2: tetra-n-butylammonium dihydrogen phosphate With triethylamine In acetonitrile at 20℃; for 3h; Inert atmosphere; Molecular sieve; Stage #3: uridine 5'-monophosphate morpholidate With pyridine at 20℃; for 48h; Inert atmosphere; | 1; 2; 3 Embodiment 1 first step synthesis general method General procedure: In a 25 mL round-bottomed flask, 1 g of acetylated glycal 1 was repeatedly dissolved in an appropriate amount of benzene for 3 times by rotary evaporation, and finally dissolved in 12 mL of benzene, and dried HCl (g) was poured into the reaction solution and stirred at room temperature. Reaction for 30min, TLC detects the reaction progress (petroleum ether: ethyl acetate=1:1), after the alkenose reaction is complete, HCl (g) and benzene are removed by distillation under reduced pressure to obtain a pale yellow syrupy mixture 2, which can be directly carried out next reaction. Embodiment 2 second step synthesis general method In a 50 mL round-bottomed flask, the mixture of 2 obtained above was dissolved in 25 mL of anhydrous CH3CN, the pH of the solution was adjusted to ≈ 9 with Et3N, the molecular sieves activated at high temperature were added, and the mixture was cooled in an ice-water bath. Dissolve 1.5g Bu4NH2PO4 in 12mL anhydrous CH3CN, under the protection of N2, add the Bu4NH2PO4 solution dropwise to the above 2 mixture, and the mixture reacts at room temperature for about 3h. The progress of the reaction was detected by TLC (with CH2Cl2:CH3OH:H2O:Et3N=16:8:0.2:0.3),After the reaction, the residual liquid was subjected to silica gel column chromatography with the system of CH2Cl2/CH3OH/H2O/Et3N=24/6/0.2/0.3 as eluent to obtain acetylated 2-deoxysugar-phosphate tetrabutylammonium salt 3. Embodiment 3 Synthesis general method of the third stepDissolve 0.05g of acetylated 2-deoxysugar-1-phosphate tetrabutylammonium salt 3 in a 25mL pear-shaped bottle, dissolve it with a small amount of anhydrous pyridine and rotate it, repeat 3 times, add 0.05g of UMP-morpholidate, and then add 0.01 g of UMP-morpholidate g tetrazole, finally added 0.5mL anhydrous pyridine as the reaction solvent, the whole reaction system was reacted under the protection of N2 gas for 48h, the reaction was detected by TLC, and the developing solvent was CHCl3:CH3OH:25%NH4OH:H2O=3.5:2:0.2:0.2 After the reaction, pyridine was evaporated, and pure uridine diphosphate acetylated-2-deoxysugar 4 was obtained by silica gel column chromatography (gradient elution with CHCl3:CH3OH:25% NH4OH:H2O system). |
Tags: UMP-morpholidate | 27908-36-7
Precautionary Statements-General | |
| Code | Phrase |
| P101 | If medical advice is needed,have product container or label at hand. |
| P102 | Keep out of reach of children. |
| P103 | Read label before use |
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| Code | Phrase |
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| P202 | Do not handle until all safety precautions have been read and understood. |
| P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
| P211 | Do not spray on an open flame or other ignition source. |
| P220 | Keep/Store away from clothing/combustible materials. |
| P221 | Take any precaution to avoid mixing with combustibles |
| P222 | Do not allow contact with air. |
| P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
| P230 | Keep wetted |
| P231 | Handle under inert gas. |
| P232 | Protect from moisture. |
| P233 | Keep container tightly closed. |
| P234 | Keep only in original container. |
| P235 | Keep cool |
| P240 | Ground/bond container and receiving equipment. |
| P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
| P242 | Use only non-sparking tools. |
| P243 | Take precautionary measures against static discharge. |
| P244 | Keep reduction valves free from grease and oil. |
| P250 | Do not subject to grinding/shock/friction. |
| P251 | Pressurized container: Do not pierce or burn, even after use. |
| P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
| P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
| P262 | Do not get in eyes, on skin, or on clothing. |
| P263 | Avoid contact during pregnancy/while nursing. |
| P264 | Wash hands thoroughly after handling. |
| P265 | Wash skin thouroughly after handling. |
| P270 | Do not eat, drink or smoke when using this product. |
| P271 | Use only outdoors or in a well-ventilated area. |
| P272 | Contaminated work clothing should not be allowed out of the workplace. |
| P273 | Avoid release to the environment. |
| P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
| P281 | Use personal protective equipment as required. |
| P282 | Wear cold insulating gloves/face shield/eye protection. |
| P283 | Wear fire/flame resistant/retardant clothing. |
| P284 | Wear respiratory protection. |
| P285 | In case of inadequate ventilation wear respiratory protection. |
| P231 + P232 | Handle under inert gas. Protect from moisture. |
| P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
| Code | Phrase |
| P301 | IF SWALLOWED: |
| P304 | IF INHALED: |
| P305 | IF IN EYES: |
| P306 | IF ON CLOTHING: |
| P307 | IF exposed: |
| P308 | IF exposed or concerned: |
| P309 | IF exposed or if you feel unwell: |
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| P311 | Call a POISON CENTER or doctor/physician. |
| P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
| P313 | Get medical advice/attention. |
| P314 | Get medical advice/attention if you feel unwell. |
| P315 | Get immediate medical advice/attention. |
| P320 | |
| P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
| P321 | |
| P322 | |
| P330 | Rinse mouth. |
| P331 | Do NOT induce vomiting. |
| P332 | IF SKIN irritation occurs: |
| P333 | If skin irritation or rash occurs: |
| P334 | Immerse in cool water/wrap n wet bandages. |
| P335 | Brush off loose particles from skin. |
| P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
| P337 | If eye irritation persists: |
| P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
| P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
| P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
| P342 | If experiencing respiratory symptoms: |
| P350 | Gently wash with plenty of soap and water. |
| P351 | Rinse cautiously with water for several minutes. |
| P352 | Wash with plenty of soap and water. |
| P353 | Rinse skin with water/shower. |
| P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
| P361 | Remove/Take off immediately all contaminated clothing. |
| P362 | Take off contaminated clothing and wash before reuse. |
| P363 | Wash contaminated clothing before reuse. |
| P370 | In case of fire: |
| P371 | In case of major fire and large quantities: |
| P372 | Explosion risk in case of fire. |
| P373 | DO NOT fight fire when fire reaches explosives. |
| P374 | Fight fire with normal precautions from a reasonable distance. |
| P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
| P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
| P378 | |
| P380 | Evacuate area. |
| P381 | Eliminate all ignition sources if safe to do so. |
| P390 | Absorb spillage to prevent material damage. |
| P391 | Collect spillage. Hazardous to the aquatic environment |
| P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
| P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
| P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
| P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
| P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
| P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
| P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
| P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
| P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
| P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
| P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
| P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
| P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
| P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
| P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
| P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
| P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
| P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
| P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
| P370 + P376 | In case of fire: Stop leak if safe to Do so. |
| P370 + P378 | In case of fire: |
| P370 + P380 | In case of fire: Evacuate area. |
| P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
| P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
| Code | Phrase |
| P401 | |
| P402 | Store in a dry place. |
| P403 | Store in a well-ventilated place. |
| P404 | Store in a closed container. |
| P405 | Store locked up. |
| P406 | Store in corrosive resistant/ container with a resistant inner liner. |
| P407 | Maintain air gap between stacks/pallets. |
| P410 | Protect from sunlight. |
| P411 | |
| P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
| P413 | |
| P420 | Store away from other materials. |
| P422 | |
| P402 + P404 | Store in a dry place. Store in a closed container. |
| P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
| P403 + P235 | Store in a well-ventilated place. Keep cool. |
| P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
| P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
| P411 + P235 | Keep cool. |
Disposal | |
| Code | Phrase |
| P501 | Dispose of contents/container to ... |
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Physical hazards | |
| Code | Phrase |
| H200 | Unstable explosive |
| H201 | Explosive; mass explosion hazard |
| H202 | Explosive; severe projection hazard |
| H203 | Explosive; fire, blast or projection hazard |
| H204 | Fire or projection hazard |
| H205 | May mass explode in fire |
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| H221 | Flammable gas |
| H222 | Extremely flammable aerosol |
| H223 | Flammable aerosol |
| H224 | Extremely flammable liquid and vapour |
| H225 | Highly flammable liquid and vapour |
| H226 | Flammable liquid and vapour |
| H227 | Combustible liquid |
| H228 | Flammable solid |
| H229 | Pressurized container: may burst if heated |
| H230 | May react explosively even in the absence of air |
| H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
| H240 | Heating may cause an explosion |
| H241 | Heating may cause a fire or explosion |
| H242 | Heating may cause a fire |
| H250 | Catches fire spontaneously if exposed to air |
| H251 | Self-heating; may catch fire |
| H252 | Self-heating in large quantities; may catch fire |
| H260 | In contact with water releases flammable gases which may ignite spontaneously |
| H261 | In contact with water releases flammable gas |
| H270 | May cause or intensify fire; oxidizer |
| H271 | May cause fire or explosion; strong oxidizer |
| H272 | May intensify fire; oxidizer |
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| H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
| H290 | May be corrosive to metals |
Health hazards | |
| Code | Phrase |
| H300 | Fatal if swallowed |
| H301 | Toxic if swallowed |
| H302 | Harmful if swallowed |
| H303 | May be harmful if swallowed |
| H304 | May be fatal if swallowed and enters airways |
| H305 | May be harmful if swallowed and enters airways |
| H310 | Fatal in contact with skin |
| H311 | Toxic in contact with skin |
| H312 | Harmful in contact with skin |
| H313 | May be harmful in contact with skin |
| H314 | Causes severe skin burns and eye damage |
| H315 | Causes skin irritation |
| H316 | Causes mild skin irritation |
| H317 | May cause an allergic skin reaction |
| H318 | Causes serious eye damage |
| H319 | Causes serious eye irritation |
| H320 | Causes eye irritation |
| H330 | Fatal if inhaled |
| H331 | Toxic if inhaled |
| H332 | Harmful if inhaled |
| H333 | May be harmful if inhaled |
| H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
| H335 | May cause respiratory irritation |
| H336 | May cause drowsiness or dizziness |
| H340 | May cause genetic defects |
| H341 | Suspected of causing genetic defects |
| H350 | May cause cancer |
| H351 | Suspected of causing cancer |
| H360 | May damage fertility or the unborn child |
| H361 | Suspected of damaging fertility or the unborn child |
| H361d | Suspected of damaging the unborn child |
| H362 | May cause harm to breast-fed children |
| H370 | Causes damage to organs |
| H371 | May cause damage to organs |
| H372 | Causes damage to organs through prolonged or repeated exposure |
| H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
| Code | Phrase |
| H400 | Very toxic to aquatic life |
| H401 | Toxic to aquatic life |
| H402 | Harmful to aquatic life |
| H410 | Very toxic to aquatic life with long-lasting effects |
| H411 | Toxic to aquatic life with long-lasting effects |
| H412 | Harmful to aquatic life with long-lasting effects |
| H413 | May cause long-lasting harmful effects to aquatic life |
| H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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