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32780-32-8

Basic Information
CAS No.: 32780-32-8
Name: Validamine
Article Data: 15
Molecular Structure:
Molecular Structure of 32780-32-8 (Validamine)
Formula: C7H15NO4
Molecular Weight: 177.2
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);
Density: 1.434 g/cm3
Boiling Point: 345.6 °C at 760 mmHg
Flash Point: 162.8 °C
Appearance: white powder
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
ConditionsYield
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
ConditionsYield
(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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With ammonium sulfate; Flavobacterium saccharophilum IFO 13984; magnesium sulfate In phosphate buffer for 96h; pH=7.1; Hydrolysis; Title compound not separated from byproducts;
38231-86-6

valienamine

A

32780-32-8

validamine

B

38231-87-7

5-epi-validamine

Conditions
ConditionsYield
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

D

37248-47-8

validamycin A

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

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

Uses

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

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)- .

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