130525-58-5

Basic information

• Product Name: D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID
• Synonyms: Methyl 5-acetamido-7,8,9-O-triacetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate;(4S,5R,6R)-5-ACETYLAMINO-4-AZIDO-6-(1S,2R,3-TRIACETOXYPROPYL)-5,6-DIHYDRO-4H-PYRAN-2-CARBOXYLIC ACID;Zanamivir Azide Triacetate Methyl Ester;Methyl7,8,9-tri-O-acetyl-N-acetyl-2-deoxy-2,3-didehydro-4a-azido-D-neuraminate;Methyl 5-acetaMido-7,8,9-O-triacetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonat;5-(AcetylaMino)-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic Acid Methyl Ester 7,8,9-Triacetate;ZanaMivir interMediate3;ZanaMivir Azide
• CAS NO: 130525-58-5
• Molecular Formula: C₁₈H₂₄N₄O₁₀
• Molecular Weight: 456.406
• Product Categories: Anti-virals;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 130525-58-5.mol

Chemical Properties

• Appearance: Off-white solid
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID(130525-58-5)
• EPA Substance Registry System: D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID(130525-58-5)

Safety Data

• Hazardous Substances Data: 130525-58-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID is used as an intermediate for the synthesis of Zanamivir derivatives, which are essential in the development of antiviral medications targeting influenza viruses. Its role in the pharmaceutical industry is vital for creating effective treatments against viral infections.
Used in Chemical Industry:
In the chemical industry, D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID serves as a key intermediate in the production of various chemical compounds. Its unique structure allows for further modification and synthesis, leading to the creation of a wide range of products with diverse applications in different sectors.

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

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

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 (78850-37-0) → methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5)

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 (80973-54-2) → methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5)

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 (366018-39-5) → methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5)

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 (80973-54-2) → 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-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5)

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 (163860-78-4) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5) + (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)

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 (639476-14-5) → methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5)

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 (691356-36-2) → methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5)

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

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)

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 (639476-04-3) → methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5)

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

(4R,5S,6R,7R,8R)-N4-benzyl-N4-acetyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene (639476-05-4) → methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5)

Conditions

Yield

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

Conditions

Yield

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

Conditions

Yield

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

Conditions

Yield

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Conditions

Yield

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

Conditions

Yield

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) → 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)

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

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

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) → (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	Yield
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) + N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (152120-54-2, 862686-58-6, 1143572-00-2) → (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	Yield
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) + methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5) → (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	Yield
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-2,7,8,9-tetra-O-acetyl-4-azido-3,4,5-trideoxy-3-iodo-D-erythro-α-L-manno-non-2-ulopyranosonate

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

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

Conditions	Yield
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 + methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5) → C38H48N4O14

Conditions	Yield
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) + 2,4,6-tris(prop-2-ynyloxy)-1,3,5-triazine (15911-93-0) → 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	Yield
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) + methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5) → (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	Yield
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) + 1,3,5-tris(prop-2-yn-1-yloxy)benzene (114233-80-6) → 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	Yield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 17h;	85%

C20H30N2O3S + methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5) → C37H52N4O13

Conditions	Yield
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) + methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5) → 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	Yield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 4h;	84%

1-chloro-4-pentyne (14267-92-6) + methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5) → 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	Yield
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) + methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5) → 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	Yield
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) + methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5) → 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 (171241-95-5)

Conditions	Yield
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) + propynoic acid benzylamide (87605-11-6) → 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	Yield
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) + 2-methyl-but-3-yn-2-ol (115-19-5) → 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	Yield
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) + trifluoroacetic anhydride (407-25-0) → 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	Yield
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) + methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5) → 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	Yield
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) + heptafluorobutyric anhydride (336-59-4) → 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	Yield
With triethylamine In acetonitrile at 0 - 135℃; Sealed tube;	78%

2-ethynylaniline (52670-38-9) + methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5) → 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	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In methanol; water at 45℃;	77%

Fmoc-N-propargylamine (127896-08-6) + methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5) → 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	Yield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 18h;	69%

Upstream product

• 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 
• 1372800-41-3 N-((4R,5R,6R,7R)-6,7,8-tris(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)oct-1-en-4-yl)acetamide 
• 1372800-42-4 N-((3R,4R,5R,6R)-5,6,7-tris(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)-1-oxoheptan-3-yl)acetamide 
• 1372800-43-5 (5R,6R,7R,8R,E)-methyl 5-acetamido-7,8,9-tris(benzyloxy)-2,6-bis((tert-butyldimethylsilyl)oxy)non-2-enoate 
• 1372800-46-8 C₂₅H₂₉NO₁₂ 
• 1372800-32-2 (4S,5R,E)-1-((4-methoxybenzyl)oxy)-5-nitroocta-2,7-dien-4-ol 
• 1372800-34-4 tert-butyl ((4R,5S,E)-5-hydroxy-8-((4-methoxybenzyl)oxy)octa-1,6-dien-4-yl)carbamate 
• 1372800-35-5 (4R,5S)-tert-butyl 4-allyl-5-((E)-3-((4-methoxybenzyl)oxy)prop-1-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1372800-36-6 (4R,5S)-tert-butyl 4-allyl-5-((E)-3-hydroxyprop-1-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1372800-37-7 (4R,5R)-tert-butyl 4-allyl-5-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1372800-38-8 (4R,5R)-tert-butyl 4-allyl-2,2-dimethyl-5-((1R,2R)-1,2,3-trihydroxypropyl)oxazolidine-3-carboxylate 
• 1372800-39-9 (4R,5R)-tert-butyl 4-allyl-2,2-dimethyl-5-((1S,2R)-1,2,3-tris(benzyloxy)propyl)oxazolidine-3-carboxylate 
• 1372800-40-2 N-((4R,5R,6S,7R)-6,7,8-tris(benzyloxy)-5-hydroxyoct-1-en-4-yl)acetamide 

Downstream Products

• 1304780-11-7 methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-cyclohexenyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate 
• 1304780-12-8 methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-phenyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate 
• 1304780-13-9 methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-(4-fluorophenyl)-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate 

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