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130525-58-5

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Basic Information
CAS No.: 130525-58-5
Name: D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID
Article Data: 22
Molecular Structure:
Molecular Structure of 130525-58-5 (D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID)
Formula: C18H24N4O10
Molecular Weight: 456.409
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;
Appearance: Off-white solid
PSA: 193.28000
LogP: -0.10414
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Synthetic route
163860-77-3

methyl (5-acetamido-7,8,9-tri-O-acetyl-4-azido-2-chloro-3,4,5-trideoxy-β-D-glycerol-D-galacto-2-nonulopyranosid)onate

130525-58-5

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

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

methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate

130525-58-5

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

Conditions
ConditionsYield
With trimethylsilylazide In tert-butyl alcohol for 10h; Inert atmosphere; Reflux;96%
Stage #1: methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate With trimethylsilylazide In tert-butyl alcohol for 10h; Inert atmosphere; Reflux;
Stage #2: With hydrogenchloride; sodium nitrite In water; ethyl acetate; tert-butyl alcohol at 20℃; for 0.5h;		96%
Stage #1: methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate With trimethylsilylazide In tert-butyl alcohol for 10h; Inert atmosphere; Reflux;
Stage #2: With hydrogenchloride; sodium nitrite In water		96%
80973-54-2

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

130525-58-5

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

Conditions
ConditionsYield
With diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene for 23h; Ambient temperature;87%
With 1,8-diazabicyclo[5.4.0]-undecen-7-ene; diphenylphosphoranyl azide In benzene85%
366018-39-5

C18H23NO10

130525-58-5

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

Conditions
ConditionsYield
Stage #1: C18H23NO10 With trimethylsilylazide In tert-butyl alcohol Inert atmosphere; Reflux;
Stage #2: With hydrogenchloride; sodium nitrite In water; tert-butyl alcohol for 1h;		76%
With trimethylsilylazide In butan-1-ol
With trimethylsilylazide In butan-1-ol
80973-54-2

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

A

130525-59-6

methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-2,3-didehydro-2,3,4,5-tetradeoxy-D-glycero-D-talo-2-nonulopyranosidonate

B

130525-58-5

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

Conditions
ConditionsYield
With ammonia; triphenylphosphine; diethylazodicarboxylate In toluene at 0℃; for 14h;A 17%
B 67%
With ammonia; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 14h;A 52%
B 34%
163860-78-4

methyl (methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-3,4,5-trideoxy-2-thio-D-glycero-α-D-galacto-nonulopyranosid)onate

4064-06-6

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

A

130525-58-5

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

B

163860-80-8

(2R,4S,5R,6R)-5-Acetylamino-4-azido-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

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

N-{(R)-1-[(S)-Hydroxy-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-but-3-enyl}-acetamide

130525-58-5

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

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 84 percent / Et3N / CH2Cl2 / 2 h / 20 °C
2: 87 percent / NaH / tetrahydrofuran / 24 h / 40 °C
3: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating
4: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C
5: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C
6: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C
7: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C
8: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C
9: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C
10: 65 percent / pyridine / 12 h / 20 °C
11: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C
12: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C
View Scheme
691356-36-2

Methanesulfonic acid (1S,2R)-2-acetylamino-1-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-pent-4-enyl ester

130525-58-5

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

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 87 percent / NaH / tetrahydrofuran / 24 h / 40 °C
2: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating
3: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C
4: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C
5: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C
6: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C
7: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C
8: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C
9: 65 percent / pyridine / 12 h / 20 °C
10: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C
11: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C
View Scheme

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

130525-58-5

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

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1: 56 percent / diethyl ether / 0 - 25 °C
2: 88 percent / Et3N / CH2Cl2
3: 82 percent / Li; NH3 / tetrahydrofuran / 1 h / -40 °C
4: 84 percent / Et3N / CH2Cl2 / 2 h / 20 °C
5: 87 percent / NaH / tetrahydrofuran / 24 h / 40 °C
6: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating
7: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C
8: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C
9: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C
10: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C
11: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C
12: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C
13: 65 percent / pyridine / 12 h / 20 °C
14: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C
15: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C
View Scheme
639476-04-3

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

130525-58-5

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

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: 88 percent / Et3N / CH2Cl2
2: 82 percent / Li; NH3 / tetrahydrofuran / 1 h / -40 °C
3: 84 percent / Et3N / CH2Cl2 / 2 h / 20 °C
4: 87 percent / NaH / tetrahydrofuran / 24 h / 40 °C
5: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating
6: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C
7: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C
8: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C
9: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C
10: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C
11: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C
12: 65 percent / pyridine / 12 h / 20 °C
13: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C
14: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C
View Scheme
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  •  ZHEJIANG JIUZHOU CHEM CO.,LTD

    China (Mainland)  |  Contact Details

    Business Type:Trading Company

    Tel:+86 19334956669

    Address:Waisha Road,Jiaojiang

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

  • Casno:

    130525-58-5

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

    Min.Order: 100 Gram

    FOB Price:  USD $ 0.0-0.0

    Exhibition in shanghai Our Laboratoy Our factory Package & Shipment Appearance:White Solid Storage:2-8, cold storage, to avoid light storage.

    Henan Sunlake Enterprise Corporation is located in Henan Province , the central plain of China , which enjoys favorable geogeaphical position and convenient transportion. The compa

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     China (Mainland)  |  Contact Details

    Business Type:Trading Company

    Tel:+86-371- 86259723

    Address:Mingmen International Center, NO.222 Dongming Road,Zhengzhou,Henan,China

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  • High Quality D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID

  • Casno:

    130525-58-5

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

    Min.Order: 1 Gram

    FOB Price:  USD $ 1.0-1.0

    Qingdao Sigma Chemical Ltd is is a global chemical industry manufacturers and suppliers of pharmaceuticals and intermediates, peptide,Nootropis etc API, food and feed additives, herbal extracts, agrochemicals and fine chemicals etc. Our Labo

    QINGDAO SIGMA CHEMICAL is mainly engaged in R&D, manufacturing and marketing pharmaceuticals, chemical intermediates, Biochemicals, Veterinary medicines and Nutrition products. Wit

  • Qingdao Sigma Chemical Co., Ltd.

     China (Mainland)  |  Contact Details

    Business Type:Trading Company

    Tel:+86-18661891880

    Address:shandong qingdao

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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