Product Name

  • Name

    D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID

  • EINECS
  • CAS No. 130525-58-5
  • Article Data22
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point
  • Formula C18H24N4O10
  • Boiling Point
  • Molecular Weight 456.409
  • Flash Point
  • Transport Information
  • Appearance Off-white solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 130525-58-5 (D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID)
  • Hazard Symbols
  • 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;
  • PSA 193.28000
  • LogP -0.10414

Synthetic route

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
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

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

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-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%
Methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-talo-non-2-enonate
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

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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%
C18H23NO10
366018-39-5

C18H23NO10

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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
Methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-talo-non-2-enonate
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

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
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

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

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
4064-06-6

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
130525-58-5

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
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;
...Expand
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
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

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

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

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

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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
(4R,5S,6R,7R,8R)-N4-benzyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene
639476-04-3

(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
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
(4R,5S,6R,7R,8R)-N4-benzyl-N4-acetyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene
639476-05-4

(4R,5S,6R,7R,8R)-N4-benzyl-N4-acetyl-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
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 13 steps
1: 82 percent / Li; NH3 / tetrahydrofuran / 1 h / -40 °C
2: 84 percent / Et3N / CH2Cl2 / 2 h / 20 °C
3: 87 percent / NaH / tetrahydrofuran / 24 h / 40 °C
4: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating
5: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C
6: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C
7: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C
8: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C
9: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C
10: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C
11: 65 percent / pyridine / 12 h / 20 °C
12: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C
13: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C
View Scheme
1-[(2R,3R)-2-Allyl-3-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-aziridin-1-yl]-ethanone
639476-15-6

1-[(2R,3R)-2-Allyl-3-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-aziridin-1-yl]-ethanone

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 10 steps
1: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating
2: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C
3: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C
4: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C
5: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C
6: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C
7: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C
8: 65 percent / pyridine / 12 h / 20 °C
9: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C
10: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C
View Scheme
(1R,2S)-2-Azido-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-pent-4-enylamine
639476-17-8

(1R,2S)-2-Azido-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-pent-4-enylamine

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 9 steps
1: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C
2: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C
3: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C
4: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C
5: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C
6: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C
7: 65 percent / pyridine / 12 h / 20 °C
8: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C
9: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C
View Scheme
N-[(1R,2S)-2-Azido-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-pent-4-enyl]-acetamide
639476-18-9

N-[(1R,2S)-2-Azido-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-pent-4-enyl]-acetamide

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 8 steps
1: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C
2: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C
3: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C
4: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C
5: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C
6: 65 percent / pyridine / 12 h / 20 °C
7: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C
8: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C
View Scheme
N-[(1R,2S)-2-Azido-4,5-dihydroxy-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-pentyl]-acetamide
725725-05-3

N-[(1R,2S)-2-Azido-4,5-dihydroxy-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-pentyl]-acetamide

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 7 steps
1: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C
2: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C
3: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C
4: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C
5: 65 percent / pyridine / 12 h / 20 °C
6: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C
7: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C
View Scheme
(2S,4S,5R,6R)-5-Acetylamino-4-azido-2-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
725725-09-7

(2S,4S,5R,6R)-5-Acetylamino-4-azido-2-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 3 steps
1: 65 percent / pyridine / 12 h / 20 °C
2: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C
3: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C
View Scheme
(4S,5R)-5-Acetylamino-4-azido-2-hydroxy-5-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-pentanoic acid

(4S,5R)-5-Acetylamino-4-azido-2-hydroxy-5-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-pentanoic acid

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 6 steps
1: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C
2: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C
3: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C
4: 65 percent / pyridine / 12 h / 20 °C
5: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C
6: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C
View Scheme
(4S,5R)-5-Acetylamino-4-azido-2-oxo-5-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-pentanoic acid methyl ester
725725-07-5

(4S,5R)-5-Acetylamino-4-azido-2-oxo-5-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-pentanoic acid methyl ester

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 4 steps
1: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C
2: 65 percent / pyridine / 12 h / 20 °C
3: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C
4: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C
View Scheme
(4S,5R)-5-Acetylamino-4-azido-2-hydroxy-5-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-pentanoic acid methyl ester
725725-06-4

(4S,5R)-5-Acetylamino-4-azido-2-hydroxy-5-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-pentanoic acid methyl ester

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 5 steps
1: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C
2: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C
3: 65 percent / pyridine / 12 h / 20 °C
4: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C
5: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C
View Scheme
(2R,4S,5R,6R)-2-Acetoxy-5-acetylamino-4-azido-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
725725-10-0

(2R,4S,5R,6R)-2-Acetoxy-5-acetylamino-4-azido-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 2 steps
1: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C
2: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C
View Scheme
N-acetylneuraminic acid methyl ester
20298-35-5, 22900-11-4, 100678-43-1, 109121-98-4, 109122-00-1, 119241-60-0, 119241-61-1, 119241-62-2

N-acetylneuraminic acid methyl ester

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 6 steps
1: 42 h / Ambient temperature
2: HCl(g) / acetonitrile / 20 h / -42 - 20 °C
3: 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Ambient temperature
4: BF3*Et2O / benzene; methanol / 18 h / Ambient temperature
5: 50percent aq. AcOH / ethyl acetate / Ambient temperature
6: 87 percent / diphenylphosphoryl azide, 1,8-diazabicyclo<5.4.0>undec-7-ene / 23 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: pyridine
2: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 3 h / 50 °C
3: trimethylsilylazide / tert-butyl alcohol / 9 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: pyridine; dmap
2: trimethylsilyl trifluoromethanesulfonate / ethyl acetate
3: trimethylsilylazide / tert-butyl alcohol
View Scheme
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate
73960-72-2

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 3 steps
1: BF3*Et2O / benzene; methanol / 18 h / Ambient temperature
2: 50percent aq. AcOH / ethyl acetate / Ambient temperature
3: 87 percent / diphenylphosphoryl azide, 1,8-diazabicyclo<5.4.0>undec-7-ene / 23 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 96 percent / MeOH, BF3*Et2O / CH2Cl2 / 16 h / 25 - 30 °C
2: 82.5 percent / Me3Si-azide / 2-methyl-propan-2-ol / 4 h / 80 °C
View Scheme
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl chloride
132883-18-2

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl chloride

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 4 steps
1: 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Ambient temperature
2: BF3*Et2O / benzene; methanol / 18 h / Ambient temperature
3: 50percent aq. AcOH / ethyl acetate / Ambient temperature
4: 87 percent / diphenylphosphoryl azide, 1,8-diazabicyclo<5.4.0>undec-7-ene / 23 h / Ambient temperature
View Scheme
methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate
6931-68-6, 72690-21-2, 74006-95-4, 108740-37-0, 108740-38-1, 108740-39-2, 119241-63-3, 119241-64-4, 119241-65-5, 147129-72-4, 147129-73-5, 73208-82-9

methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 5 steps
1: HCl(g) / acetonitrile / 20 h / -42 - 20 °C
2: 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Ambient temperature
3: BF3*Et2O / benzene; methanol / 18 h / Ambient temperature
4: 50percent aq. AcOH / ethyl acetate / Ambient temperature
5: 87 percent / diphenylphosphoryl azide, 1,8-diazabicyclo<5.4.0>undec-7-ene / 23 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 3 h / 50 °C
2: trimethylsilylazide / tert-butyl alcohol / 9 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 3 h / 50 °C
2: trimethylsilylazide / tert-butyl alcohol / 9 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: trimethylsilyl trifluoromethanesulfonate / ethyl acetate
2: trimethylsilylazide / tert-butyl alcohol
View Scheme
Multi-step reaction with 2 steps
1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 50 °C
2: trimethylsilylazide / tert-butyl alcohol / 80 °C
View Scheme
(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate
108740-39-2, 6931-68-6, 72690-21-2, 73208-82-9, 108740-37-0, 108740-38-1, 119241-63-3, 119241-64-4, 119241-65-5, 147129-72-4, 147129-73-5, 74006-95-4

(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 3 steps
1: 82 percent / Me3SiSO3CF3 / acetonitrile / 2 h / 50 °C
2: 77 percent / trifluoroacetic acid / tetrahydrofuran / Ambient temperature
3: 67 percent / PPh3, NH3, DEAD / toluene / 14 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1.1: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 3 h / 30 - 52 °C / Inert atmosphere
2.1: trimethylsilylazide / tert-butyl alcohol / Inert atmosphere; Reflux
2.2: 1 h
View Scheme
Multi-step reaction with 2 steps
1: trimethylsilyl trifluoromethanesulfonate / ethyl acetate
2: trimethylsilylazide / butan-1-ol
View Scheme
N-acetyl neuraminic acid
6813-81-6, 14120-72-0, 19342-33-7, 21646-00-4, 82349-00-6, 99395-98-9, 99395-99-0, 99396-00-6, 102734-10-1, 489-46-3, 140671-47-2, 140850-42-6, 140850-43-7, 140850-44-8, 145375-13-9

N-acetyl neuraminic acid

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 4 steps
1: Amberlite IR120 (H+)
2: pyridine
3: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 3 h / 50 °C
4: trimethylsilylazide / tert-butyl alcohol / 9 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: H+ resin
2: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 50 °C
3: trimethylsilylazide / tert-butyl alcohol / 80 °C
View Scheme
N-acetyl neuraminic acid
19342-33-7

N-acetyl neuraminic acid

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 4 steps
1.1: Dowex-50 (H+) / 40 - 45 °C
2.1: pyridine / 20 °C / Cooling with ice
3.1: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 3 h / 30 - 52 °C / Inert atmosphere
4.1: trimethylsilylazide / tert-butyl alcohol / Inert atmosphere; Reflux
4.2: 1 h
View Scheme
Multi-step reaction with 4 steps
1: Dowex H+
2: pyridine
3: trimethylsilyl trifluoromethanesulfonate / ethyl acetate
4: trimethylsilylazide / butan-1-ol
View Scheme
Multi-step reaction with 4 steps
1: Dowex 50W-X4(H+) / 20 °C
2: dmap / pyridine / 0.25 h / Cooling with ice
3: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 3.5 h / 30 - 52 °C / Inert atmosphere
4: trimethylsilylazide / tert-butyl alcohol / 10 h / Inert atmosphere; Reflux
View Scheme
N-acetylneuraminic acid methyl ester
20298-35-5, 22900-11-4, 100678-43-1, 109121-98-4, 109122-00-1, 119241-60-0, 119241-61-1, 119241-62-2

N-acetylneuraminic acid methyl ester

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 3 steps
1.1: pyridine / 20 °C / Cooling with ice
2.1: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 3 h / 30 - 52 °C / Inert atmosphere
3.1: trimethylsilylazide / tert-butyl alcohol / Inert atmosphere; Reflux
3.2: 1 h
View Scheme
Multi-step reaction with 3 steps
1: pyridine
2: trimethylsilyl trifluoromethanesulfonate / ethyl acetate
3: trimethylsilylazide / butan-1-ol
View Scheme
Multi-step reaction with 3 steps
1: dmap / pyridine / 0.25 h / Cooling with ice
2: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 3.5 h / 30 - 52 °C / Inert atmosphere
3: trimethylsilylazide / tert-butyl alcohol / 10 h / Inert atmosphere; Reflux
View Scheme
N-((4R,5R,6R,7R)-6,7,8-tris(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)oct-1-en-4-yl)acetamide
1372800-41-3

N-((4R,5R,6R,7R)-6,7,8-tris(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)oct-1-en-4-yl)acetamide

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere
2: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere
3: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere
4: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
5: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere
6: 30% Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere
7: pyridine; dmap / 5.5 h / 20 °C / Inert atmosphere
8: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere
9: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere
10: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere
11: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere
View Scheme
N-((3R,4R,5R,6R)-5,6,7-tris(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)-1-oxoheptan-3-yl)acetamide
1372800-42-4

N-((3R,4R,5R,6R)-5,6,7-tris(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)-1-oxoheptan-3-yl)acetamide

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
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 9 steps
1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere
2: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
3: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere
4: 30% Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere
5: pyridine; dmap / 5.5 h / 20 °C / Inert atmosphere
6: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere
7: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere
8: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere
9: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere
View Scheme
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-amino-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester
139110-70-6

5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-amino-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester

Conditions
ConditionsYield
With hydrogen In ethanol at 20℃; for 9h;100%
With ammonium chloride; zinc In ethanol; water at 20 - 30℃; for 0.5h;94%
With ammonium chloride; zinc In water at 20 - 30℃;94%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

5-acetamido-7,8,9-tri-O-acetyl-4-(N-tert-butoxycarbonyl)-amino-2,3,4,5-tetradeoxy-D-glycero-D-galacto-non-2-enopyranosonic acid methyl ester

5-acetamido-7,8,9-tri-O-acetyl-4-(N-tert-butoxycarbonyl)-amino-2,3,4,5-tetradeoxy-D-glycero-D-galacto-non-2-enopyranosonic acid methyl ester

Conditions
ConditionsYield
With hydrogen In ethyl acetate at 50℃; under 760.051 Torr; for 48h;98%
Stage #1: methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate With triphenylphosphine In tetrahydrofuran; water at 85℃; for 4h;
Stage #2: di-tert-butyl dicarbonate With triethylamine In tetrahydrofuran; water at 0 - 20℃; for 3h;		82%
With 5%-palladium/activated carbon; hydrogen In methanol at 20℃; for 1h;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

methyl 5-[acetyl(tert-butoxycarbonyl)amino]-7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate
171886-97-8

methyl 5-[acetyl(tert-butoxycarbonyl)amino]-7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate

Conditions
ConditionsYield
With dmap In tetrahydrofuran at 60℃; Inert atmosphere;96%
With dmap In 1,4-dioxane 1.) RT, 89 h, 2.) 80 deg C, 2 h;86%
With dmap In 1,4-dioxane at 20℃; for 12h;50%
With dmap In tetrahydrofuran for 2h; Reflux;
N-propargyl 3β-hydroxyolean-12-en-28-amide

N-propargyl 3β-hydroxyolean-12-en-28-amide

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

(5R)-acetylamino-(4S)-[4-[(3β-hydroxyolean-12-en-28-oyl)amino]methyl-1,2,3-triazol-1-yl]-(6R)-((1S,2R)-1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

(5R)-acetylamino-(4S)-[4-[(3β-hydroxyolean-12-en-28-oyl)amino]methyl-1,2,3-triazol-1-yl]-(6R)-((1S,2R)-1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate In dichloromethane; water at 20℃; for 12h;93%
N-propargyl 3β-dihydroxyurs-12-en-28-amide

N-propargyl 3β-dihydroxyurs-12-en-28-amide

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

(5R)-acetylamino-(4S)-[4-[(3β-hydroxyurs-12-en-28-oyl)amino]methyl-1,2,3-triazol-1-yl]-(6R)-((1S,2R)-1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

(5R)-acetylamino-(4S)-[4-[(3β-hydroxyurs-12-en-28-oyl)amino]methyl-1,2,3-triazol-1-yl]-(6R)-((1S,2R)-1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate In dichloromethane; water at 20℃; for 12h;93%
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine
152120-54-2, 862686-58-6, 1143572-00-2

N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine

(1S,2R)-1-((2R,3R,45)-3-acetamido-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-6-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

(1S,2R)-1-((2R,3R,45)-3-acetamido-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-6-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

Conditions
ConditionsYield
Stage #1: methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate With triphenylphosphine In tetrahydrofuran at 13 - 20℃; for 2.33333h;
Stage #2: With water; lithium hydroxide In tetrahydrofuran for 28h;
Stage #3: N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine With dmap In tetrahydrofuran; water for 36h;		92.8%
Stage #1: methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate With hydrogen In ethanol under 760.051 Torr; for 8h;
Stage #2: N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine In tetrahydrofuran at 20℃; for 18h;		50%
Stage #1: methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate With Lindlar's catalyst In ethanol under 760.051 Torr; for 8h;
Stage #2: N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine In tetrahydrofuran; ethanol at 20℃; for 18h;		50%
N-propargyl 3β, 16α-dihydroxyolean-12-en-28-amide
1438766-95-0

N-propargyl 3β, 16α-dihydroxyolean-12-en-28-amide

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

(5R)-acetylamino-(4S)-[4-[(3β,16α-dihydroxyolean-12-en-28-oyl)amino]methyl-1,2,3-triazol-1-yl]-(6R)-((1S,2R)-1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

(5R)-acetylamino-(4S)-[4-[(3β,16α-dihydroxyolean-12-en-28-oyl)amino]methyl-1,2,3-triazol-1-yl]-(6R)-((1S,2R)-1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate In dichloromethane; water at 20℃; for 12h;91%
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

methyl 5-acetamido-2,7,8,9-tetra-O-acetyl-4-azido-3,4,5-trideoxy-3-iodo-D-erythro-α-L-manno-non-2-ulopyranosonate

methyl 5-acetamido-2,7,8,9-tetra-O-acetyl-4-azido-3,4,5-trideoxy-3-iodo-D-erythro-α-L-manno-non-2-ulopyranosonate

Conditions
ConditionsYield
With N-iodo-succinimide; sodium acetate; acetic acid at 20℃; for 1.5h;90%
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid

5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid

Conditions
ConditionsYield
Stage #1: methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate With sodium methylate In methanol
Stage #2: With sodium hydroxide		89%
Stage #1: methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate With sodium methylate In methanol at 0℃; for 0.5h;
Stage #2: With lithium hydroxide monohydrate In tetrahydrofuran; water at 0℃; for 0.5h;
Stage #3: In tetrahydrofuran; water		61%
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester
152178-79-5

5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester

Conditions
ConditionsYield
With methanol; sodium methylate at 20℃; for 3h;88%
With sodium methylate In methanol at 21℃; for 2.5h;71.2%
Stage #1: methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate With sodium methylate In methanol at 20℃; for 2h;
Stage #2: With hydrogenchloride In 1,4-dioxane; methanol pH=6 - 7;		69%
Stage #1: methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate; sodium methylate In methanol at 20℃; for 1h;
Stage #2: With Dowex-50x8 (H+) In methanol		66%
With methanol; sodium methylate for 2h; Cooling with ice;
C21H26N2O4S

C21H26N2O4S

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

C38H48N4O14

C38H48N4O14

Conditions
ConditionsYield
Stage #1: methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate With hydrogen In methanol at 20℃; for 14h; Inert atmosphere;
Stage #2: C21H26N2O4S With triethylamine; mercury dichloride In dichloromethane at 20℃; for 6h; Inert atmosphere;		88%
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

2,4,6-tris(prop-2-ynyloxy)-1,3,5-triazine
15911-93-0

2,4,6-tris(prop-2-ynyloxy)-1,3,5-triazine

2,4,6-tris-2-yloxymethyl-{5-acetylamino-6-(1,2,3-triacetoxypropyl)-4-[1,2,3]-2-yloxymethyl-1-yl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester}-[1,3,5]triazine

2,4,6-tris-2-yloxymethyl-{5-acetylamino-6-(1,2,3-triacetoxypropyl)-4-[1,2,3]-2-yloxymethyl-1-yl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester}-[1,3,5]triazine

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 4h;87%
N-propargyl-3β-hydroxy-lup-20(29)-en-28-amide
1596376-96-3

N-propargyl-3β-hydroxy-lup-20(29)-en-28-amide

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

(5R)-acetylamino-(4S)-[4-[(3β-hydroxylup-20(29)-en-28-oyl)amino]methyl-1,2,3-triazol-1-yl]-(6R)-((1S,2R)-1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

(5R)-acetylamino-(4S)-[4-[(3β-hydroxylup-20(29)-en-28-oyl)amino]methyl-1,2,3-triazol-1-yl]-(6R)-((1S,2R)-1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate In dichloromethane; water at 20℃; for 12h;87%
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

1,3,5-tris(prop-2-yn-1-yloxy)benzene
114233-80-6

1,3,5-tris(prop-2-yn-1-yloxy)benzene

2,4,6-tris-2-yloxymethyl-{5-acetylamino-6-(1,2,3-triacetoxypropyl)-4-[1,2,3]-2-yloxymethyl-1-yl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester}-[1,3,5]benzene

2,4,6-tris-2-yloxymethyl-{5-acetylamino-6-(1,2,3-triacetoxypropyl)-4-[1,2,3]-2-yloxymethyl-1-yl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester}-[1,3,5]benzene

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 17h;85%
C20H30N2O3S

C20H30N2O3S

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

C37H52N4O13

C37H52N4O13

Conditions
ConditionsYield
Stage #1: methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate With hydrogen In methanol at 20℃; for 14h; Inert atmosphere;
Stage #2: C20H30N2O3S With triethylamine; mercury dichloride In dichloromethane at 20℃; for 6h; Inert atmosphere;		85%
1-Pentyne
627-19-0

1-Pentyne

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,4,5-trideoxy-4-(4-propyl-[1,2,3]triazol-1-yl)-D-glycero-D-galacto-non-2-enonate

methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,4,5-trideoxy-4-(4-propyl-[1,2,3]triazol-1-yl)-D-glycero-D-galacto-non-2-enonate

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 4h;84%
1-chloro-4-pentyne
14267-92-6

1-chloro-4-pentyne

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

5-acetylamino-4-[4-(3-chloropropyl)-[1,2,3]triazol-1-yl]-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

5-acetylamino-4-[4-(3-chloropropyl)-[1,2,3]triazol-1-yl]-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 4h;83%
pent-1-yn-5-ol
5390-04-5

pent-1-yn-5-ol

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

5-acetylamino-4-[4-(3-hydroxypropyl)-[1,2,3]triazol-1-yl]-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

5-acetylamino-4-[4-(3-hydroxypropyl)-[1,2,3]triazol-1-yl]-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 1.5h;82%
With copper(II) sulfate; sodium L-ascorbate In ethanol; water at 25℃;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

methyl 7,8,9-tri-O-acetyl-2,6-anhydro-5-(tert-butoxycarboxyamido)-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enoate
171241-95-5

methyl 7,8,9-tri-O-acetyl-2,6-anhydro-5-(tert-butoxycarboxyamido)-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enoate

Conditions
ConditionsYield
Stage #1: di-tert-butyl dicarbonate; methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate With dmap In tetrahydrofuran for 2h; Reflux;
Stage #2: With sodium methylate In methanol at 0℃; for 1h;		82%
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

propynoic acid benzylamide
87605-11-6

propynoic acid benzylamide

5-acetylamino-4-(4-benzoylaminocarbonyl-[1,2,3]triazol-1-yl)-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

5-acetylamino-4-(4-benzoylaminocarbonyl-[1,2,3]triazol-1-yl)-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 1.5h;81%
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

5-acetylamino-4-[4-(1-hydroxy-1-methylethyl)-[1,2,3]triazol-1-yl]-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

5-acetylamino-4-[4-(1-hydroxy-1-methylethyl)-[1,2,3]triazol-1-yl]-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 1.5h;80%
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

methyl 7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-5-(2,2,2-trifluoroacetamido)-D-glycero-D-galacto-non-2-enonate

methyl 7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-5-(2,2,2-trifluoroacetamido)-D-glycero-D-galacto-non-2-enonate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 0 - 135℃; Sealed tube;80%
In acetonitrile at 135℃; for 0.166667h; Microwave irradiation;75%
2,2,3,3,3-pentafluoropropanoic anhydride
356-42-3

2,2,3,3,3-pentafluoropropanoic anhydride

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

methyl 7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-5-(2,2,3,3,3-pentafluoropropionamido)-D-glycero-D-galacto-non-2-enonate

methyl 7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-5-(2,2,3,3,3-pentafluoropropionamido)-D-glycero-D-galacto-non-2-enonate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 0 - 135℃; Sealed tube;78%
methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

heptafluorobutyric anhydride
336-59-4

heptafluorobutyric anhydride

methyl 7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-5-(2,2,3,3,4,4,4-heptafluorobutyramido)-D-glycero-D-galacto-non-2-enonate

methyl 7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-5-(2,2,3,3,4,4,4-heptafluorobutyramido)-D-glycero-D-galacto-non-2-enonate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 0 - 135℃; Sealed tube;78%
2-ethynylaniline
52670-38-9

2-ethynylaniline

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

methyl 5-acetamido-7,8,9-tri-O-acetyl-4-(4-((2-aminophenyl)-1H-1,2,3-triazol-1-yl))-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate

methyl 5-acetamido-7,8,9-tri-O-acetyl-4-(4-((2-aminophenyl)-1H-1,2,3-triazol-1-yl))-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In methanol; water at 45℃;77%
Fmoc-N-propargylamine
127896-08-6

Fmoc-N-propargylamine

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
130525-58-5

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

5-acetylamino-4-{4-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-[1,2,3]triazol-1-yl}-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

5-acetylamino-4-{4-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-[1,2,3]triazol-1-yl}-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 18h;69%

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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