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Name |
Methyl 5-acetamido-7,8,9-O-triacetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate |
EINECS | N/A |
CAS No. | 130525-58-5 | Density | N/A |
PSA | 193.28000 | LogP | -0.10414 |
Solubility | N/A | Melting Point |
N/A |
Formula | C18H24N4O10 | Boiling Point | N/A |
Molecular Weight | 456.409 | Flash Point | N/A |
Transport Information | N/A | Appearance | Off-white solid |
Safety | Risk Codes | N/A | |
Molecular Structure | Hazard Symbols | N/A | |
Synonyms |
methyl 7,8,9-tri-O-acetyl-5-(acetylamino)-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate;D-glycero-D-galacto-non-2-enonic acid, 5-(acetylamino)-2,6-anhydro-4-azido-3,4,5-trideoxy-, methyl ester, 7,8,9-triacetate; |
Article Data | 22 |
methyl (5-acetamido-7,8,9-tri-O-acetyl-4-azido-2-chloro-3,4,5-trideoxy-β-D-glycerol-D-galacto-2-nonulopyranosid)onate
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 10℃; for 1h; | 98% |
methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
Conditions | Yield |
---|---|
With trimethylsilylazide In tert-butyl alcohol for 10h; Inert atmosphere; Reflux; | 96% |
Stage #1: methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate With trimethylsilylazide In tert-butyl alcohol for 10h; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride; sodium nitrite In water; ethyl acetate; tert-butyl alcohol at 20℃; for 0.5h; | 96% |
Stage #1: methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate With trimethylsilylazide In tert-butyl alcohol for 10h; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride; sodium nitrite In water | 96% |
Methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-talo-non-2-enonate
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
Conditions | Yield |
---|---|
With diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene for 23h; Ambient temperature; | 87% |
With 1,8-diazabicyclo[5.4.0]-undecen-7-ene; diphenylphosphoranyl azide In benzene | 85% |
C18H23NO10
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
Conditions | Yield |
---|---|
Stage #1: C18H23NO10 With trimethylsilylazide In tert-butyl alcohol Inert atmosphere; Reflux; Stage #2: With hydrogenchloride; sodium nitrite In water; tert-butyl alcohol for 1h; | 76% |
With trimethylsilylazide In butan-1-ol | |
With trimethylsilylazide In butan-1-ol |
Methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-talo-non-2-enonate
A
methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-2,3-didehydro-2,3,4,5-tetradeoxy-D-glycero-D-talo-2-nonulopyranosidonate
B
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
Conditions | Yield |
---|---|
With ammonia; triphenylphosphine; diethylazodicarboxylate In toluene at 0℃; for 14h; | A 17% B 67% |
With ammonia; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 14h; | A 52% B 34% |
methyl (methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-3,4,5-trideoxy-2-thio-D-glycero-α-D-galacto-nonulopyranosid)onate
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
A
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
B
(2R,4S,5R,6R)-5-Acetylamino-4-azido-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With methylsulfenyl bromide; 3 A molecular sieve; silver trifluoromethanesulfonate In 1,2-dichloro-ethane; acetonitrile at -38℃; for 16h; Yield given; |
N-{(R)-1-[(S)-Hydroxy-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-but-3-enyl}-acetamide
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1: 84 percent / Et3N / CH2Cl2 / 2 h / 20 °C 2: 87 percent / NaH / tetrahydrofuran / 24 h / 40 °C 3: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating 4: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C 5: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C 6: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C 7: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C 8: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C 9: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C 10: 65 percent / pyridine / 12 h / 20 °C 11: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C 12: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C View Scheme |
Methanesulfonic acid (1S,2R)-2-acetylamino-1-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-pent-4-enyl ester
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: 87 percent / NaH / tetrahydrofuran / 24 h / 40 °C 2: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating 3: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C 4: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C 5: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C 6: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C 7: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C 8: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C 9: 65 percent / pyridine / 12 h / 20 °C 10: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C 11: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C View Scheme |
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1: 56 percent / diethyl ether / 0 - 25 °C 2: 88 percent / Et3N / CH2Cl2 3: 82 percent / Li; NH3 / tetrahydrofuran / 1 h / -40 °C 4: 84 percent / Et3N / CH2Cl2 / 2 h / 20 °C 5: 87 percent / NaH / tetrahydrofuran / 24 h / 40 °C 6: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating 7: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C 8: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C 9: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C 10: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C 11: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C 12: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C 13: 65 percent / pyridine / 12 h / 20 °C 14: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C 15: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C View Scheme |
(4R,5S,6R,7R,8R)-N4-benzyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 14 steps 1: 88 percent / Et3N / CH2Cl2 2: 82 percent / Li; NH3 / tetrahydrofuran / 1 h / -40 °C 3: 84 percent / Et3N / CH2Cl2 / 2 h / 20 °C 4: 87 percent / NaH / tetrahydrofuran / 24 h / 40 °C 5: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating 6: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C 7: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C 8: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C 9: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C 10: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C 11: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C 12: 65 percent / pyridine / 12 h / 20 °C 13: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C 14: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C View Scheme |
The Methyl 5-acetamido-7,8,9-O-triacetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate, with the CAS registry number 130525-58-5, has the systematic name of methyl 7,8,9-tri-O-acetyl-5-(acetylamino)-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate. And the molecular formula of the chemical is C18H24N4O10.
The characteristics of this chemical are as followings: (1)ACD/LogP: 0.74; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -1; (4)ACD/LogD (pH 7.4): -1; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 12; (8)ACD/KOC (pH 7.4): 12; (9)#H bond acceptors: 14; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 13; (12)Polar Surface Area: 155.89 Å2.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: CC(=O)NC1C(C=C(OC1C(C(COC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)N=[N+]=[N-]
(2)InChI: InChI=1/C18H24N4O10/c1-8(23)20-15-12(21-22-19)6-13(18(27)28-5)32-17(15)16(31-11(4)26)14(30-10(3)25)7-29-9(2)24/h6,12,14-17H,7H2,1-5H3,(H,20,23)/t12-,14+,15+,16+,17+/m0/s1
(3)InChIKey: ANKWFOHGBMGGAL-IIHMKKKEBE