Validamine supplier | CasNO.32780-32-8

Name
Validamine
EINECS
CAS No. 32780-32-8
Article Data15
CAS DataBase
Density 1.434 g/cm³
Solubility
Melting Point
Formula C₇H₁₅NO₄
Boiling Point 345.6 °C at 760 mmHg
Molecular Weight 177.2
Flash Point 162.8 °C
Transport Information
Appearance white powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1-Amino-1,5,6-trideoxy-5-(hydroxymethyl)-D-chiro-inositol;PT141 Acetate;(1R,2S,3S,4S,6R)-4-amino-6-(methoxymethyl)cyclohexane-1,2,3-triol;PT-141;1D-1-amino-1,5,6-trideoxy-5-(hydroxymethyl)-chiro-inositol;D-chiro-Inositol, 1-amino-1,5,6-trideoxy-5-(hydroxymethyl)-;(1R,2S,3S,4S,6R)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol;D-chiro-Inositol,1-amino-1,5,6-trideoxy-5- (hydroxymethyl)-;PT141;Bremelanotide (PT-141);(1R,2S,3S,4S)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol;Validamine PT 141 Acetate;Ac-Nle-Asp-His-D-Phe-Arg-Trp-Lys-OH;PT-141 (Bremelanotide);
PSA 106.94000
LogP -1.89110

Synthetic route

: 1316231-06-7
benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)carbamate

: 32780-32-8
validamine

Conditions

Conditions	Yield
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol; water; ethyl acetate under 760.051 Torr; for 20h;	95%

: 73411-05-9, 73651-21-5
β-D-Glucopyranosylvalidamin-octaacetat

: 32780-32-8
validamine

Conditions

Conditions	Yield
(i) NH3, MeOH, (ii) NaIO4, (iii) (hydrolysis); Multistep reaction;

: 68108-50-9
(1S)-(+)-(1,2,4/3,5)-1-acetamido-2,3,4-triacetoxy-5-acetoxymethylcyclohexane

: 32780-32-8
validamine

Conditions

Conditions	Yield
With sodium methylate; hydrazine hydrate 1.) RT, 2 h, 2.) 100 deg C, 72 h; Yield given. Multistep reaction;
With sodium methylate; hydrazine hydrate 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h; Yield given. Multistep reaction;
With hydrogenchloride at 80℃; for 2h;
Multi-step reaction with 2 steps 1: 10percent NaOMe / methanol / 3 h / 25 °C 2: 80percent aq. NH2NH2 / 72 h / 100 °C / sealed tube View Scheme

: 124492-65-5
N-((1S,2S,3S,4R,5R)-2,3,4-Trihydroxy-5-hydroxymethyl-cyclohexyl)-acetamide

: 32780-32-8
validamine

Conditions

Conditions	Yield
With hydrazine hydrate at 100℃; for 72h; sealed tube; Yield given;

: (1S,2R,3R,4R,6S)-6-Amino-2,3-bis-benzyloxy-4-benzyloxymethyl-cyclohexanol

: 32780-32-8
validamine

Conditions

Conditions	Yield
With ammonia; sodium In tetrahydrofuran at -40℃; for 1.5h;

: 3-O-acetyl 4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-(p-tolylsulfonyl)-5a-carba-D-glucopyranosylamine

A: 32780-32-8
validamine

B: 191740-46-2
2-epi-Validamine

Conditions

Conditions	Yield
With hydrogenchloride; sodium benzoate; barium dihydroxide 1) DMF, 140 deg C, 120 h, 2) MeOH, reflux, 30 min, 3) H2O, 80 deg C, 4 h; Yield given. Multistep reaction;

: 191723-81-6
2,3-di-O-acetyl-N-benzyloxycarbonyl-4,6-di-O-(p-tolylsulfonyl)-5a-carba-D-glucopyranosylamine

A: 32780-32-8
validamine

B: 4-epi-validamine

Conditions

Conditions	Yield
With sodium benzoate; barium dihydroxide 1) DMF, 140 deg C, 120 h, 2) H2O, 80 deg C, 4 h; Yield given. Multistep reaction;

: 37248-47-8
validamycin A

A: 38665-10-0
(+)-validoxylamine A

B: 32780-32-8
validamine

C: 38231-86-6
valienamine

Conditions

Conditions	Yield
With ammonium sulfate; Flavobacterium saccharophilum IFO 13984; magnesium sulfate In phosphate buffer for 96h; pH=7.1; Hydrolysis; Title compound not separated from byproducts;

...Expand

: 38231-86-6
valienamine

A: 32780-32-8
validamine

B: 38231-87-7
5-epi-validamine

Conditions

Conditions	Yield
With hydrogen; nickel In water at 20℃; under 2068.59 Torr; for 20h;	A 152 mg B n/a

: 2280-44-6
D-Glucose

culture medium: culture medium

A: 32780-32-8
validamine

B: 38231-86-6
valienamine

C: 39318-73-5, 81691-72-7, 81739-22-2
validoxylamine A

D: 37248-47-8
validamycin A

Conditions

Conditions	Yield
With Streptomyces hygroscopicus var. limoneus In water at 28℃; for 168h; Further byproducts.;

...Expand

: 2280-44-6
D-Glucose

culture medium: culture medium

A: 32780-32-8
validamine

B: 38231-86-6
valienamine

C: 37248-47-8
validamycin A

D: validamycin B

Conditions

Conditions	Yield
With Streptomyces hygroscopicus var. limoneus In water at 28℃; for 168h; Further byproducts.;

...Expand

: 89859-47-2
(1R)-(1,3,4/2,6)-1,7-O-benzylidene-4-<(benzyloxycarbonyl)amino>-6-C-(hydroxymethyl)-1,2,3-cyclohexanetriol

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 89.6 percent / pyridine / 8 h / Ambient temperature 2: 0.5 N HCl / methanol / 0.5 h / Heating 3: 4.5 g / pyridine; CH2Cl2 / 14 h / Ambient temperature 4: 1) sodium benzoate, 2) Ba(OH)2 / 1) DMF, 140 deg C, 120 h, 2) H2O, 80 deg C, 4 h View Scheme
Multi-step reaction with 3 steps 1: CH2Cl2; pyridine / 14 h / Ambient temperature 2: 4.8 g / pyridine; CH2Cl2 / 15 h / Ambient temperature 3: 1) sodium benzoate, 2) N HCl, 3) Ba(OH)2 / 1) DMF, 140 deg C, 120 h, 2) MeOH, reflux, 30 min, 3) H2O, 80 deg C, 4 h View Scheme

: Acetic acid (1S,2S,3S,5R,6R)-2-acetoxy-3-benzyloxycarbonylamino-6-hydroxy-5-hydroxymethyl-cyclohexyl ester

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 4.5 g / pyridine; CH2Cl2 / 14 h / Ambient temperature 2: 1) sodium benzoate, 2) Ba(OH)2 / 1) DMF, 140 deg C, 120 h, 2) H2O, 80 deg C, 4 h View Scheme

: 2,3-di-O-acetyl-4,6-O-benzylidene-N-benzyloxycarbonyl-5a-carba-D-glucopyranosylamine

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 0.5 N HCl / methanol / 0.5 h / Heating 2: 4.5 g / pyridine; CH2Cl2 / 14 h / Ambient temperature 3: 1) sodium benzoate, 2) Ba(OH)2 / 1) DMF, 140 deg C, 120 h, 2) H2O, 80 deg C, 4 h View Scheme

: Toluene-4-sulfonic acid (4aR,6S,7S,8S,8aR)-6-benzyloxycarbonylamino-8-hydroxy-2-phenyl-hexahydro-benzo[1,3]dioxin-7-yl ester

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 4.8 g / pyridine; CH2Cl2 / 15 h / Ambient temperature 2: 1) sodium benzoate, 2) N HCl, 3) Ba(OH)2 / 1) DMF, 140 deg C, 120 h, 2) MeOH, reflux, 30 min, 3) H2O, 80 deg C, 4 h View Scheme

: 151693-59-3
(1R,2R,3S,4R,5R)-3,4-di-O-benzyl-5-benzyloxymethyl-1,2-O,O-sulfonyl-cyclohexane-1,2,3,4-tetraol

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) LiN3, 2.) aq. H2SO4 / 1.) DMF, 105 deg C, 2.5 h, 2.) THF, 50 deg C, 30 min 2: 96 percent / pyridine / CH2Cl2 / 0.5 h / 0 °C 3: 89 percent / tetrahydrofuran / 3 h / 80 °C 4: 98 percent / NaOMe / methanol / 6 h / Ambient temperature 5: H2 / Raney nickel / ethyl acetate / 18 h / Ambient temperature 6: Na, NH3 / tetrahydrofuran / 1.5 h / -40 °C View Scheme

: 166376-50-7
(1R,2R,3R,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-3-O-(trifluoromethylsulfonyl)-1,2,3-cyclohexanetriol

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 89 percent / tetrahydrofuran / 3 h / 80 °C 2: 98 percent / NaOMe / methanol / 6 h / Ambient temperature 3: H2 / Raney nickel / ethyl acetate / 18 h / Ambient temperature 4: Na, NH3 / tetrahydrofuran / 1.5 h / -40 °C View Scheme

: 166376-48-3
(1R,2R,3R,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 96 percent / pyridine / CH2Cl2 / 0.5 h / 0 °C 2: 89 percent / tetrahydrofuran / 3 h / 80 °C 3: 98 percent / NaOMe / methanol / 6 h / Ambient temperature 4: H2 / Raney nickel / ethyl acetate / 18 h / Ambient temperature 5: Na, NH3 / tetrahydrofuran / 1.5 h / -40 °C View Scheme

: 166376-52-9
(1R,2R,3S,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Raney nickel / ethyl acetate / 18 h / Ambient temperature 2: Na, NH3 / tetrahydrofuran / 1.5 h / -40 °C View Scheme

: 166376-51-8
(1R,2R,3S,4S,6R)-3-O-Acetyl-4-azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 98 percent / NaOMe / methanol / 6 h / Ambient temperature 2: H2 / Raney nickel / ethyl acetate / 18 h / Ambient temperature 3: Na, NH3 / tetrahydrofuran / 1.5 h / -40 °C View Scheme

: 5040-08-4
1,2-O-isopropylidene-α-D-glucofuranurono-5-ulose-6,3-lactone

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 86 percent / KF / 6 h / 20 °C 2: 79 percent / D-camphorsulfonic acid / CH2Cl2 / 0.75 h / 25 °C 3: 83 percent / NaBH4 / propan-2-ol / 2 h / 25 °C 4: 178 mg / pyridine / CH2Cl2 / 0.5 h / 25 °C 5: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C 6: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C 7: 64 percent / p-TsOH / 2 h / 25 °C 8: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h 9: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C 10: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h 11: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h View Scheme
Multi-step reaction with 11 steps 1: 86 percent / KF / 6 h / 20 °C 2: 79 percent / D-camphorsulfonic acid / CH2Cl2 / 0.75 h / 25 °C 3: NaBH4 / ethanol / Ambient temperature 4: 178 mg / pyridine / CH2Cl2 / 0.5 h / 25 °C 5: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C 6: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C 7: 64 percent / p-TsOH / 2 h / 25 °C 8: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h 9: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C 10: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h 11: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h View Scheme

Yield

Multi-step reaction with 11 steps
1: 86 percent / KF / 6 h / 20 °C
2: 79 percent / D-camphorsulfonic acid / CH2Cl2 / 0.75 h / 25 °C
3: 83 percent / NaBH4 / propan-2-ol / 2 h / 25 °C
4: 178 mg / pyridine / CH2Cl2 / 0.5 h / 25 °C
5: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C
6: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C
7: 64 percent / p-TsOH / 2 h / 25 °C
8: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h
9: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C
10: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h
11: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h
View Scheme

Multi-step reaction with 11 steps
1: 86 percent / KF / 6 h / 20 °C
2: 79 percent / D-camphorsulfonic acid / CH2Cl2 / 0.75 h / 25 °C
3: NaBH4 / ethanol / Ambient temperature
4: 178 mg / pyridine / CH2Cl2 / 0.5 h / 25 °C
5: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C
6: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C
7: 64 percent / p-TsOH / 2 h / 25 °C
8: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h
9: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C
10: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h
11: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h
View Scheme

: (3aR,5R,6S,6aR)-5-((R)-1-Hydroxymethyl-2-nitro-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 178 mg / pyridine / CH2Cl2 / 0.5 h / 25 °C 2: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C 3: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C 4: 64 percent / p-TsOH / 2 h / 25 °C 5: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h 6: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C 7: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h 8: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h View Scheme

Yield

Multi-step reaction with 8 steps
1: 178 mg / pyridine / CH2Cl2 / 0.5 h / 25 °C
2: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C
3: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C
4: 64 percent / p-TsOH / 2 h / 25 °C
5: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h
6: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C
7: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h
8: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h
View Scheme

: 152434-60-1
(3aR,3bS,6S,6aS,7aR)-6-Hydroxy-2,2-dimethyl-6-nitromethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 79 percent / D-camphorsulfonic acid / CH2Cl2 / 0.75 h / 25 °C 2: 83 percent / NaBH4 / propan-2-ol / 2 h / 25 °C 3: 178 mg / pyridine / CH2Cl2 / 0.5 h / 25 °C 4: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C 5: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C 6: 64 percent / p-TsOH / 2 h / 25 °C 7: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h 8: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C 9: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h 10: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h View Scheme
Multi-step reaction with 10 steps 1: 79 percent / D-camphorsulfonic acid / CH2Cl2 / 0.75 h / 25 °C 2: NaBH4 / ethanol / Ambient temperature 3: 178 mg / pyridine / CH2Cl2 / 0.5 h / 25 °C 4: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C 5: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C 6: 64 percent / p-TsOH / 2 h / 25 °C 7: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h 8: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C 9: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h 10: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h View Scheme

Yield

Multi-step reaction with 10 steps
1: 79 percent / D-camphorsulfonic acid / CH2Cl2 / 0.75 h / 25 °C
2: 83 percent / NaBH4 / propan-2-ol / 2 h / 25 °C
3: 178 mg / pyridine / CH2Cl2 / 0.5 h / 25 °C
4: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C
5: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C
6: 64 percent / p-TsOH / 2 h / 25 °C
7: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h
8: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C
9: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h
10: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h
View Scheme

Multi-step reaction with 10 steps
1: 79 percent / D-camphorsulfonic acid / CH2Cl2 / 0.75 h / 25 °C
2: NaBH4 / ethanol / Ambient temperature
3: 178 mg / pyridine / CH2Cl2 / 0.5 h / 25 °C
4: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C
5: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C
6: 64 percent / p-TsOH / 2 h / 25 °C
7: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h
8: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C
9: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h
10: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h
View Scheme

: C21H21NO9

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C 2: 64 percent / p-TsOH / 2 h / 25 °C 3: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h 4: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C 5: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h 6: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h View Scheme

Yield

Multi-step reaction with 6 steps
1: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C
2: 64 percent / p-TsOH / 2 h / 25 °C
3: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h
4: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C
5: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h
6: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h
View Scheme

: 152434-63-4
C24H25NO9

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C 2: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C 3: 64 percent / p-TsOH / 2 h / 25 °C 4: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h 5: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C 6: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h 7: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h View Scheme

Yield

Multi-step reaction with 7 steps
1: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C
2: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C
3: 64 percent / p-TsOH / 2 h / 25 °C
4: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h
5: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C
6: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h
7: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h
View Scheme

: C27H29NO9

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h 2: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h View Scheme
Multi-step reaction with 2 steps 1: 1.) 1percent methanolic NaOMe, 2.) pyridine / 1.) RT, 3 h, 2.) RT, 3 h 2: 1.) 1percent methanolic NaOMe, 2.) 80percent aq. NH2NH2 / 1.) RT, 2 h, 2.) 100 deg C, 72 h View Scheme

: C27H28N2O11

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C 2: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h 3: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h View Scheme
Multi-step reaction with 3 steps 1: 50 percent / n-Bu3SnH, 2,2'-azobisisobutyronitrile / toluene / 1 h / Heating 2: 1.) 1percent methanolic NaOMe, 2.) pyridine / 1.) RT, 3 h, 2.) RT, 3 h 3: 1.) 1percent methanolic NaOMe, 2.) 80percent aq. NH2NH2 / 1.) RT, 2 h, 2.) 100 deg C, 72 h View Scheme

: C21H21NO9

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 64 percent / p-TsOH / 2 h / 25 °C 2: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h 3: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C 4: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h 5: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h View Scheme

: C27H27NO12

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h 2: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C 3: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h 4: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h View Scheme
Multi-step reaction with 4 steps 1: 1.) liq. NH3, 2.) p-TsOH 2: 50 percent / n-Bu3SnH, 2,2'-azobisisobutyronitrile / toluene / 1 h / Heating 3: 1.) 1percent methanolic NaOMe, 2.) pyridine / 1.) RT, 3 h, 2.) RT, 3 h 4: 1.) 1percent methanolic NaOMe, 2.) 80percent aq. NH2NH2 / 1.) RT, 2 h, 2.) 100 deg C, 72 h View Scheme

: 152434-61-2
(3aR,3bS,6S,6aS,7aR)-6-(2-Ethoxy-ethoxy)-2,2-dimethyl-6-nitromethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one

: 32780-32-8
validamine

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 83 percent / NaBH4 / propan-2-ol / 2 h / 25 °C 2: 178 mg / pyridine / CH2Cl2 / 0.5 h / 25 °C 3: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C 4: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C 5: 64 percent / p-TsOH / 2 h / 25 °C 6: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h 7: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C 8: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h 9: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h View Scheme
Multi-step reaction with 9 steps 1: NaBH4 / ethanol / Ambient temperature 2: 178 mg / pyridine / CH2Cl2 / 0.5 h / 25 °C 3: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C 4: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C 5: 64 percent / p-TsOH / 2 h / 25 °C 6: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h 7: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C 8: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h 9: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h View Scheme

Yield

Multi-step reaction with 9 steps
1: 83 percent / NaBH4 / propan-2-ol / 2 h / 25 °C
2: 178 mg / pyridine / CH2Cl2 / 0.5 h / 25 °C
3: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C
4: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C
5: 64 percent / p-TsOH / 2 h / 25 °C
6: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h
7: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C
8: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h
9: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h
View Scheme

Multi-step reaction with 9 steps
1: NaBH4 / ethanol / Ambient temperature
2: 178 mg / pyridine / CH2Cl2 / 0.5 h / 25 °C
3: 84 mg / aq.trifluoroacetic acid / 1 h / 40 °C
4: 140 mg / CsF / dimethylformamide / 0.5 h / 25 °C
5: 64 percent / p-TsOH / 2 h / 25 °C
6: 1.) liq.NH3, 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 9 min; 2.) 25 deg C, 2 h
7: 50 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C
8: 1.) sodium methoxide, 2.) pyridine / 1.) MeOH, 25 deg C, 3 h; 25 deg C, 12 h
9: 1.) sodium methoxide, 2.) aq. hydrazine / 1.) MeOH, 25 deg C, 2 h; 2.) 100 deg C, 72 h
View Scheme

: 32780-32-8
validamine

: 93173-26-3
2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl isothiocyanate

: 162414-07-5
N-<(1S)-(1,2,4/3,5)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl>-N'-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)thiourea

Conditions

Conditions	Yield
In water; N,N-dimethyl-formamide for 0.666667h; Ambient temperature;	92.8%

: 32780-32-8
validamine

: 501-53-1
benzyl chloroformate

: 85281-05-6
N-(benzyloxycarbonyl)validamine

Conditions

Conditions	Yield
Stage #1: validamine; benzyl chloroformate In 1,4-dioxane; water at 0 - 20℃; for 2h; Stage #2: With sodium hydrogencarbonate In 1,4-dioxane; water pH=7 - 7.5;	92%
In 1,4-dioxane; water at 0 - 20℃; for 1h;	88%
In 1,4-dioxane; water 1.) 0-5 deg C, 1 h, 2.) room temp., 1 h;	31.8 g

: 32780-32-8
validamine

: S-tert-butoxycarbonyl-2-thioxo-4,6-dimethylpyrimidine

: N-(tert-butyloxycarbonyl)-validamine

Conditions

Conditions	Yield
In 1,4-dioxane; water at 0 - 20℃; for 18h;	88.4%

: 96-26-4
dihydroxyacetone

: 32780-32-8
validamine

: 83470-79-5
N-<2-hydroxy-1-(hydroxymethyl)ethyl>validamine

Conditions

Conditions	Yield
With hydrogenchloride; sodium cyanoborohydride In N,N-dimethyl-formamide at 50 - 60℃; for 15h;	55%

: 32780-32-8
validamine

: 108-24-7
acetic anhydride

: 68108-50-9
(1S)-(+)-(1,2,4/3,5)-1-acetamido-2,3,4-triacetoxy-5-acetoxymethylcyclohexane

Conditions

Conditions	Yield
With pyridine; dmap Inert atmosphere;	52%
With pyridine; dmap for 24h; Ambient temperature; Yield given;

: 133-99-3, 490-37-9, 2152-98-9, 4482-75-1, 5965-66-2, 13299-27-9, 13360-52-6, 14641-93-1, 15548-43-3, 16462-44-5, 16984-36-4, 16984-38-6, 20869-27-6, 22688-72-8, 27452-49-9, 29276-55-9, 30608-12-9, 34481-13-5, 37169-60-1, 37169-64-5, 64234-01-1, 64234-02-2, 75281-88-8, 80446-85-1, 84413-57-0, 92344-56-4, 93221-87-5, 93301-77-0, 94799-29-8, 100427-98-3, 100428-00-0, 101312-82-7, 102046-24-2, 102046-25-3, 109432-00-0, 109432-02-2, 109432-04-4, 109432-08-8, 135268-49-4, 138231-26-2, 140461-59-2, 145414-22-8, 145414-26-2, 146339-75-5, 146339-76-6, 149116-55-2, 528-50-7
Cellobiose

: 32780-32-8
validamine

A: 73410-98-7, 145554-75-2
1-O-β-D-glucopyranosyl-1L-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol

B: 139541-64-3
validamine 2-β-glucoside

C: 145531-76-6, 145554-76-3
7-O-β-D-glucosyl validamine

Conditions

Conditions	Yield
In water at 27℃; for 72h; β-glucosidase (from Rhodotorula lactosa);	A 48 mg B 51 mg C 125 mg

...Expand

: 133-99-3, 490-37-9, 2152-98-9, 4482-75-1, 5965-66-2, 13299-27-9, 13360-52-6, 14641-93-1, 15548-43-3, 16462-44-5, 16984-36-4, 16984-38-6, 20869-27-6, 22688-72-8, 27452-49-9, 29276-55-9, 30608-12-9, 34481-13-5, 37169-60-1, 37169-64-5, 64234-01-1, 64234-02-2, 75281-88-8, 80446-85-1, 84413-57-0, 92344-56-4, 93221-87-5, 93301-77-0, 94799-29-8, 100427-98-3, 100428-00-0, 101312-82-7, 102046-24-2, 102046-25-3, 109432-00-0, 109432-02-2, 109432-04-4, 109432-08-8, 135268-49-4, 138231-26-2, 140461-59-2, 145414-22-8, 145414-26-2, 146339-75-5, 146339-76-6, 149116-55-2, 6363-53-7
Maltose

: 32780-32-8
validamine

A: 145531-77-7
validamine 7-α-isomaltoside

B: 73410-98-7, 145554-75-2
validamine 4-α-glucoside

C: 145531-76-6, 145554-76-3
validamine 7-α-glucoside

Conditions

Conditions	Yield
In water at 27℃; for 72h; α-glucosidase (from Rhodotorula lactosa);	A 22 mg B 44 mg C 106 mg

...Expand

: 32780-32-8
validamine

: 108-24-7
acetic anhydride

: 24578-12-9
Methyl 3,4-anhydro-α-D-galactopyranoside

A: Acetic acid (2R,3R,4R,5R,6S)-5-acetoxy-2-acetoxymethyl-6-methoxy-4-((1S,2S,3S,4R,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexylamino)-tetrahydro-pyran-3-yl ester

B: Acetic acid (2S,3R,4S,5R,6S)-3-acetoxy-6-acetoxymethyl-2-methoxy-5-((1S,2S,3S,4R,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexylamino)-tetrahydro-pyran-4-yl ester

Conditions

Conditions	Yield
With pyridine 1.) isopropanol, 120 deg C, 6 d, 2.) room temp., overnight; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 32780-32-8
validamine

: 162414-09-7
(1S,5S,7R,8S,1''R)-3-(5a'-carba-α-D-glucopyranosylamino)-7-(1'',2''-dihydroxyethyl)-2,6-dioxa-4-azabicyclo<3.3.0>oct-3-en-8-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 92.8 percent / dimethylformamide; H2O / 0.67 h / Ambient temperature 2: 94.8 percent / HgO / diethyl ether / 46 h / Ambient temperature 3: 85.7 percent / Na / liquid ammonia; tetrahydrofuran / 0.25 h / -78 °C View Scheme

: 32780-32-8
validamine

: 162414-08-6
(1S,3R,4R,5S,6S)-3-hydroxymethyl-8-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosylamino)-7-oxa-9-azabicyclo<4.3.0>non-8-ene-4,5-diol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 92.8 percent / dimethylformamide; H2O / 0.67 h / Ambient temperature 2: 94.8 percent / HgO / diethyl ether / 46 h / Ambient temperature View Scheme

Validamine Chemical Properties

Molecule structure of Validamine (CAS NO.32780-32-8):

IUPAC Name: (1R,2S,3S,4S,6R)-4-Amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol
Molecular Formula: C₇H₁₅NO₄
Molecular Weight: 177.198300 g/mol
Appearance: white powder
Density: 1.434 g/cm³
Boiling Point: 345.6 °C at 760 mmHg
Flash Point: 162.8 °C
Index of Refraction: 1.599
Molar Refractivity: 42.22 cm³
Molar Volume: 123.5 cm³
Surface Tension: 65.3 dyne/cm
XLogP3-AA: -2.2
H-Bond Donor: 5
H-Bond Acceptor: 5
Rotatable Bond Count: 1
Exact Mass: 177.100108
MonoIsotopic Mass: 177.100108
Topological Polar Surface Area: 107
Heavy Atom Count: 12
Canonical SMILES: C1C(C(C(C(C1N)O)O)O)CO
Isomeric SMILES: C1[C@@H]([C@H]([C@@H]([C@H]([C@H]1N)O)O)O)CO
InChI: InChI=1S/C7H15NO4/c8-4-1-3(2-9)5(10)7(12)6(4)11/h3-7,9-12H,1-2,8H2/t3-,4+,5-,6+,7+/m1/s1
InChIKey: GSQYAWMREAXBHF-UOYQFSTFSA-N
Product Categories: Amino Acid Derivatives; Peptide

Validamine Uses

Validamine (CAS NO.32780-32-8) is a kind of hormones regulating endocrine.

Validamine Specification

Validamine (CAS NO.32780-32-8) is also named as 1-Amino-1,5,6-trideoxy-5-(hydroxymethyl)-D-chiro-inositol ; D-chiro-Inositol, 1-amino-1,5,6-trideoxy-5-(hydroxymethyl)- .

Product Name

Validamine

Synthetic route

Validamine Chemical Properties

Validamine Uses

Validamine Specification

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