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

Basic information

  • Product 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
  • CasNo.:130525-58-5
  • MF:C18H24N4O10
  • MW:456.409

Physical and Chemical Properties

  • Boiling Point:
  • Packing:
  • Throughput:
Inquiry

Product Details

CasNo: 130525-58-5

MF: C18H24N4O10

Appearance: Off-white solid

Cost-effective and customizable Methyl 5-acetamido-7,8,9-O-triacetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate 130525-58-5 in stock

  • Molecular Formula:C18H24N4O10
  • Molecular Weight:456.409
  • Appearance/Colour:Off-white solid 
  • PSA:193.28000 
  • LogP:-0.10414 

D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID(Cas 130525-58-5) Usage

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

130525-58-5 Relevant articles

Catalytic asymmetric anti-selective nitroaldol reaction en Route to Zanamivir

Nitabaru, Tatsuya,Kumagai, Naoya,Shibasaki, Masakatsu

, p. 1644 - 1647 (2012)

Battling the flu: Zanamivir (Relenza) is...

A convenient method for the introduction of nitrogen and sulfur at C-4 on a sialic acid analogue

Itzstein, Mark von,Jin, Betty,Wu, Wen-Yang,Chandler, Malcolm

, p. 181 - 186 (1993)

-

SMALL MOLECULE LIGAND-TARGETED DRUG CONJUGATES FOR ANTI-INFLUENZA CHEMOTHERAPY AND IMMUNOTHERAPY

-

Page/Page column 20, (2020/02/16)

Disclosed herein is a small molecule tar...

N-ACETYLATED SIALIC ACIDS AND RELATED SIALOSIDES

-

Paragraph 0268; 0269, (2018/06/12)

The present invention provides N-acetyl ...

Synthesis of novel pentacyclic triterpene-Neu5Ac2en derivatives and investigation of their: In vitro anti-influenza entry activity

Shi, Yongying,Si, Longlong,Han, Xu,Fan, Zibo,Wang, Shouxin,Li, Man,Sun, Jiaqi,Zhang, Yongmin,Zhou, Demin,Xiao, Sulong

, p. 1531 - 1541 (2017/07/25)

Sialic acid derivatives, analogs, and th...

FATTY ACID ANTIVIRAL CONJUGATES AND THEIR USES

-

Paragraph 0755; 0763, (2016/06/01)

The invention relates to fatty acid anti...

130525-58-5 Process route

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
Conditions Yield
With trimethylsilylazide; In tert-butyl alcohol; for 10h; Inert atmosphere; Reflux;
96%
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;
With hydrogenchloride; sodium nitrite; In water; ethyl acetate; tert-butyl alcohol; at 20 ℃; for 0.5h;
96%
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;
With hydrogenchloride; sodium nitrite; In water;
96%
With trimethylsilylazide; In tert-butyl alcohol; for 10h; Reflux; Inert atmosphere;
84%
With trimethylsilylazide; In tert-butyl alcohol; at 80 ℃; for 4h;
82.5%
With trimethylsilylazide; In tert-butyl alcohol; at 80 ℃;
78%
With trimethylsilylazide; In tert-butyl alcohol; for 10.5h; Heating;
76%
With trimethylsilylazide; In tert-butyl alcohol; at 80 ℃; for 12h; Inert atmosphere;
73%
With trimethylsilylazide; In tert-butyl alcohol; at 37 ℃; for 11.5h;
60%
Multi-step reaction with 2 steps
1: 50percent aq. AcOH / ethyl acetate / Ambient temperature
2: 87 percent / diphenylphosphoryl azide, 1,8-diazabicyclo<5.4.0>undec-7-ene / 23 h / Ambient temperature
With diphenylphosphoranyl azide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethyl acetate;
Multi-step reaction with 2 steps
1: 77 percent / trifluoroacetic acid / tetrahydrofuran / Ambient temperature
2: 67 percent / PPh3, NH3, DEAD / toluene / 14 h / 0 °C
With ammonia; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; toluene;
With trimethylsilylazide; In tert-butyl alcohol; for 9h; Reflux;
With trimethylsilylazide; In tert-butyl alcohol; for 9h; Reflux;
With trimethylsilylazide;
With trimethylsilylazide; In tert-butyl alcohol;
With trimethylsilylazide; In tert-butyl alcohol;
C<sub>18</sub>H<sub>23</sub>NO<sub>10</sub>
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
Conditions Yield
C18H23NO10; With trimethylsilylazide; In tert-butyl alcohol; Inert atmosphere; Reflux;
With hydrogenchloride; sodium nitrite; In water; tert-butyl alcohol; for 1h;
76%
With trimethylsilylazide; In butan-1-ol;
With trimethylsilylazide; In butan-1-ol;

130525-58-5 Upstream products

  • 80973-54-2
    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

  • 78850-37-0
    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

  • 163860-78-4
    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
    4064-06-6

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

130525-58-5 Downstream products

  • 139110-70-6
    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

  • 139110-80-8
    139110-80-8

    zanamivir

  • 130525-61-0
    130525-61-0

    ammonium 5-acetamido-2,3-didehydro-2,3,4,5-tetradeoxy-4-(triphenylphosphoranylidenamino)-D-glycero-D-galacto-2-nonulopyranosidonate

  • 915946-73-5
    915946-73-5

    C26H29FN4O10