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192126-76-4

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Basic Information
CAS No.: 192126-76-4
Name: D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]-
Article Data: 5
Molecular Structure:
Molecular Structure of 192126-76-4 (D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]-)
Formula: C17H30 N2 O12 S
Molecular Weight: 486.497
Synonyms: Mycothiol;U 17
PSA: 284.28000
LogP: -4.77140
Related products
Synthetic route
1228173-37-2

1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol

192126-76-4

1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol

Conditions
ConditionsYield
Stage #1: 1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol With trifluoroacetic acid
Stage #2: With pyridine		100%
668481-15-0

Acetic acid (1S,2R,3R,4S,5S,6R)-2,3,4,5-tetraacetoxy-6-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-((R)-2-acetylamino-3-acetylsulfanyl-propionylamino)-tetrahydro-pyran-2-yloxy]-cyclohexyl ester

A

669091-43-4

1-D-myo-inosityl-2-(N-acetyl-L-cysteinyl)amino-2-deoxy-α-D-glucopyranoside disulfide

B

192126-76-4

1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol

Conditions
ConditionsYield
With magnesium methanolate In methanol at 20℃; for 2h;A 29%
B 40%
669091-43-4

1-D-myo-inosityl-2-(N-acetyl-L-cysteinyl)amino-2-deoxy-α-D-glucopyranoside disulfide

192126-76-4

1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol

Conditions
ConditionsYield
With Bis(2-mercaptoethyl) Sulfone In water at 20℃; for 120h;
With ethylenediaminetetraacetic acid; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid; NADPH-dependent mycothiol disulfide reductase In water; dimethyl sulfoxide at 30℃; pH=7.5; Enzyme kinetics;
18725-37-6

(R)-2-acetylamino-3-(acetylthio)propionic acid

192126-76-4

1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1,3-dicyclohexylcarbodiimide
2: 29 percent / Mg(OMe)2 / methanol / 2 h / 20 °C
3: bis(2-mercaptoethyl)sulfone / H2O / 120 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 1,3-dicyclohexylcarbodiimide
2: 40 percent / Mg(OMe)2 / methanol / 2 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 25 percent / 2,4,6-collidine; 1-hydroxy-7-azabenzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium PF6 / dimethylformamide / 0 - 20 °C
2: 29 percent / Mg(OMe)2 / methanol / 2 h / 20 °C
3: bis(2-mercaptoethyl)sulfone / H2O / 120 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 25 percent / 2,4,6-collidine; 1-hydroxy-7-azabenzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium PF6 / dimethylformamide / 0 - 20 °C
2: 40 percent / Mg(OMe)2 / methanol / 2 h / 20 °C
View Scheme
668481-13-8

Acetic acid (1S,2R,3R,4S,5S,6R)-2,3,4,5-tetraacetoxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester

192126-76-4

1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 81 percent / hydrogen; HCl / palladium on carbon / ethyl acetate / 6 h / 20 °C / 760.21 Torr
2: 1,3-dicyclohexylcarbodiimide
3: 29 percent / Mg(OMe)2 / methanol / 2 h / 20 °C
4: bis(2-mercaptoethyl)sulfone / H2O / 120 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 81 percent / hydrogen; HCl / palladium on carbon / ethyl acetate / 6 h / 20 °C / 760.21 Torr
2: 1,3-dicyclohexylcarbodiimide
3: 40 percent / Mg(OMe)2 / methanol / 2 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 81 percent / hydrogen; HCl / palladium on carbon / ethyl acetate / 6 h / 20 °C / 760.21 Torr
2: 25 percent / 2,4,6-collidine; 1-hydroxy-7-azabenzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium PF6 / dimethylformamide / 0 - 20 °C
3: 29 percent / Mg(OMe)2 / methanol / 2 h / 20 °C
4: bis(2-mercaptoethyl)sulfone / H2O / 120 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 81 percent / hydrogen; HCl / palladium on carbon / ethyl acetate / 6 h / 20 °C / 760.21 Torr
2: 25 percent / 2,4,6-collidine; 1-hydroxy-7-azabenzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium PF6 / dimethylformamide / 0 - 20 °C
3: 40 percent / Mg(OMe)2 / methanol / 2 h / 20 °C
View Scheme
668481-15-0

Acetic acid (1S,2R,3R,4S,5S,6R)-2,3,4,5-tetraacetoxy-6-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-((R)-2-acetylamino-3-acetylsulfanyl-propionylamino)-tetrahydro-pyran-2-yloxy]-cyclohexyl ester

192126-76-4

1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 29 percent / Mg(OMe)2 / methanol / 2 h / 20 °C
2: bis(2-mercaptoethyl)sulfone / H2O / 120 h / 20 °C
View Scheme

Acetic acid (1S,2R,3R,4S,5S,6R)-2,3,4,5-tetraacetoxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-amino-tetrahydro-pyran-2-yloxy)-cyclohexyl ester; hydrochloride

192126-76-4

1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1,3-dicyclohexylcarbodiimide
2: 29 percent / Mg(OMe)2 / methanol / 2 h / 20 °C
3: bis(2-mercaptoethyl)sulfone / H2O / 120 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 1,3-dicyclohexylcarbodiimide
2: 40 percent / Mg(OMe)2 / methanol / 2 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 25 percent / 2,4,6-collidine; 1-hydroxy-7-azabenzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium PF6 / dimethylformamide / 0 - 20 °C
2: 29 percent / Mg(OMe)2 / methanol / 2 h / 20 °C
3: bis(2-mercaptoethyl)sulfone / H2O / 120 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 25 percent / 2,4,6-collidine; 1-hydroxy-7-azabenzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium PF6 / dimethylformamide / 0 - 20 °C
2: 40 percent / Mg(OMe)2 / methanol / 2 h / 20 °C
View Scheme

C2HF3O2*C17H30N2O12S

192126-76-4

1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol

Conditions
ConditionsYield
With pyridine for 0.5h;3.3 mg
1228173-30-5

1-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol hydrochloride

192126-76-4

1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 4 - 20 °C / Inert atmosphere
2: trifluoroacetic acid / 0.33 h / 4 °C
3: pyridine / 0.5 h / 20 °C
View Scheme

C17H30N2O12S

192126-76-4

1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol

Conditions
ConditionsYield
With pyridine at 20℃; for 0.5h;4.4 mg
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