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Methyl 5-acetamido-7,8,9-O-triacetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate

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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 Molecular Structure of 130525-58-5 (D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID) 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-O-triacetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate Synthetic route

163860-77-3

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

130525-58-5

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 10℃; for 1h;98%
78850-37-0

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

130525-58-5

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

Conditions
ConditionsYield
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%
80973-54-2

Methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-talo-non-2-enonate

130525-58-5

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

Conditions
ConditionsYield
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 benzene85%
366018-39-5

C18H23NO10

130525-58-5

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

Conditions
ConditionsYield
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
80973-54-2

Methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-talo-non-2-enonate

A

130525-59-6

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

130525-58-5

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

Conditions
ConditionsYield
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%
163860-78-4

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

4064-06-6

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

A

130525-58-5

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

B

163860-80-8

(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
ConditionsYield
With methylsulfenyl bromide; 3 A molecular sieve; silver trifluoromethanesulfonate In 1,2-dichloro-ethane; acetonitrile at -38℃; for 16h; Yield given;
639476-14-5

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

130525-58-5

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

Conditions
ConditionsYield
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
691356-36-2

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

130525-58-5

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

Conditions
ConditionsYield
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

Benzyl-[(S)-2-benzyloxy-2-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-eth-(E)-ylidene]-amine

130525-58-5

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

Conditions
ConditionsYield
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
639476-04-3

(4R,5S,6R,7R,8R)-N4-benzyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene

130525-58-5

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

Conditions
ConditionsYield
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

Methyl 5-acetamido-7,8,9-O-triacetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate Specification

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

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