2'-Deamino-2'-hydroxyneamine

Base Information

• Chemical Name: 2'-Deamino-2'-hydroxyneamine
• CAS No.: 31077-71-1
• Molecular Formula: C12H25 N3 O7
• Molecular Weight: 323.346
• DSSTox Substance ID: DTXSID90953177
• Nikkaji Number: J122.689D
• Wikidata: Q27135699
• Metabolomics Workbench ID: 64987
• Mol file: 31077-71-1.mol

Synonyms:2'-Deamino-2'-hydroxyneamine;Kanamine;NK 1003;31077-71-1;Antibiotic NK 1003;Streptamine, 4-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl)-2-deoxy-, D-;(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxyoxane-3,4,5-triol;4-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl)-2-deoxystreptamine;(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl 6-amino-6-deoxy-alpha-D-glucopyranoside;2'-deamino-2'-hydroxy-neamine;CHEBI:67223;DTXSID90953177;NK-1003;LS-146919;C20350;Q27135699;4,6-Diamino-2,3-dihydroxycyclohexyl 6-amino-6-deoxyhexopyranoside

Chemical Property of 2'-Deamino-2'-hydroxyneamine

Chemical Property:

• Vapor Pressure: 8.04E-16mmHg at 25°C
• Boiling Point: 579.1°C at 760 mmHg
• PKA: 12.94±0.70(Predicted)
• Flash Point: 304°C
• PSA: 197.67000
• Density: 1.56g/cm³
• LogP: -2.98110
• XLogP3: -5.1
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 323.16925015
• Heavy Atom Count: 22
• Complexity: 377

Purity/Quality:

98% ^*data from raw suppliers

Kanamycin A Related Compound 1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)O)O)O)N
• Isomeric SMILES: C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)O)O)O)N

Technology Process of 2'-Deamino-2'-hydroxyneamine

There total 12 articles about 2'-Deamino-2'-hydroxyneamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(1S,2R,3R,4S,6R)-4,6-Diamino-3-((2R,3R,4S,5R,6R)-6-aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol → 4-O-(6-amino-6-deoxy-α-D-glucopyranosyl)-2-deoxystreptamine (31077-71-1)

Guidance literature:

With hydrogen; palladium dihydroxide; In water; acetic acid; for 22h; under 760 Torr; Ambient temperature;

DOI:10.1021/ja9910356

Reference yield:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) → 4-O-(6-amino-6-deoxy-α-D-glucopyranosyl)-2-deoxystreptamine (31077-71-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / pyridine / 20 h / 0 - 20 °C

2: 90 percent / NaN₃ / dimethylformamide / 5 h / 80 °C

3: 57 percent / NaH / dimethylformamide / 4.5 h / 0 - 20 °C

4: TfOH, NIS / diethyl ether; CH₂Cl₂ / 0.5 h / -15 °C

5: NaOMe / tetrahydrofuran; methanol / 19 h / Ambient temperature

6: NH₂NH₂ / 20 percent Pd(OH)2/C / methanol / 19 h / Heating

7: H₂ / 20 percent Pd(OH)2/C / acetic acid; H₂O / 22 h / 760 Torr / Ambient temperature

With pyridine; N-iodo-succinimide; sodium azide; trifluorormethanesulfonic acid; hydrogen; sodium methylate; sodium hydride; hydrazine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/ja9910356

Reference yield:

2-deoxystreptamine (2037-48-1,731753-11-0) → 4-O-(6-amino-6-deoxy-α-D-glucopyranosyl)-2-deoxystreptamine (31077-71-1)

Guidance literature:

Multi-step reaction with 7 steps

1: TfN₃, Et₃N, CuSO₄ / CH₂Cl₂; methanol / 21 h / Ambient temperature

2: pyridine, DMAP / 23 h / Ambient temperature

3: 71 percent / Novozym 435 (Candida antarctica lipase), sodium phosphate buffer (pH 6.2) / toluene / 72 h / Ambient temperature

4: TfOH, NIS / diethyl ether; CH₂Cl₂ / 0.5 h / -15 °C

5: NaOMe / tetrahydrofuran; methanol / 19 h / Ambient temperature

6: NH₂NH₂ / 20 percent Pd(OH)2/C / methanol / 19 h / Heating

7: H₂ / 20 percent Pd(OH)2/C / acetic acid; H₂O / 22 h / 760 Torr / Ambient temperature

With pyridine; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; sodium phosphate buffer; Novozym 435 (Candida antarctica lipase); triflic azide; hydrogen; sodium methylate; copper(II) sulfate; triethylamine; hydrazine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; toluene;

DOI:10.1021/ja9910356

upstream raw materials:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

2-deoxystreptamine

(1α,2β,3α,4β,6β)-4,6-Diazido-1,2,3-cyclohexantriol-triacetat

(1α,2β,3α,4β,6β)-4,6-Diazido-1,2,3-cyclohexantriol

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