(1R,3S,4R,6S)-4,6-diaminocyclohexane-1,2,3-triol dihydrochloride

Base Information

• Chemical Name: (1R,3S,4R,6S)-4,6-diaminocyclohexane-1,2,3-triol dihydrochloride
• CAS No.: 14429-30-2
• Molecular Formula: C6H14 N2 O3 . 2 Cl H
• Molecular Weight: 235.111
• Mol file: 14429-30-2.mol

Synonyms:Streptamine,2-deoxy-, dihydrochloride (8CI,9CI); 2-Deoxystreptamine dihydrochloride;Deoxystreptamine dihydrochloride

Chemical Property of (1R,3S,4R,6S)-4,6-diaminocyclohexane-1,2,3-triol dihydrochloride

Chemical Property:

• Vapor Pressure: 5.52E-05mmHg at 25°C
• Boiling Point: 310.1°Cat760mmHg
• Flash Point: 141.3°C
• Density: g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,3S,4R,6S)-4,6-diaminocyclohexane-1,2,3-triol dihydrochloride

There total 15 articles about (1R,3S,4R,6S)-4,6-diaminocyclohexane-1,2,3-triol dihydrochloride 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: 100.0%

6-azido-4-nitro-1,2,3-cyclohexanetriol → 2-Desoxy-streptamin-dihydrochlorid (14429-30-2)

Guidance literature:

With hydrogenchloride; hydrogen; platinum(IV) oxide; In water; at ordinary temperature and pressure;

DOI:10.1139/v87-246

Reference yield: 87.0%

(+/-)-4-O-acetyl-1,5,6-trideoxy-2,3-di-O-formyl-1-phthalimido-5-trichloroacetamido-muco-inositol (135743-87-2) → 1,5-diamino-1,5,6-trideoxy-muco-inositol dihydrochloride (14429-30-2,14844-05-4,15486-77-8,20183-93-1,20325-19-3,68035-83-6,89937-54-2,135820-87-0,138233-49-5)

Guidance literature:

With hydrazine; In ethanol; chloroform; at 80 ℃; for 20h;

DOI:10.1016/0008-6215(91)84073-N

Reference yield:

1,2-dideoxy-1-nitro-D-manno-heptitol (35988-91-1) → 2-Desoxy-streptamin-dihydrochlorid (14429-30-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 81 percent / CuSO₄, conc. H₂SO₄ / acetone / 20 h / Ambient temperature

2: 76 percent / pyridine / 1.5 h / 0 °C

3: 92 percent / 90 percent trifluoroacetic acid / toluene / 0.5 h / -20 °C / in two repeated steps

4: sodium metaperiodate / H₂O / 0.25 h / with ice-cooling

5: 70 percent / NaOCH₃ / methanol / 0.5 h / 25 °C

6: 90 percent trifluoroacetic acid / diethyl ether / 3 h / Heating

7: 72 percent / LiN₃ / dimethylformamide / 3 h / 100 °C

8: 100 percent / H₂, 1 M HCl / Adams catalyst / H₂O / at ordinary temperature and pressure

With hydrogenchloride; sodium periodate; lithium azide; sulfuric acid; hydrogen; sodium methylate; copper(II) sulfate; trifluoroacetic acid; platinum(IV) oxide; In pyridine; methanol; diethyl ether; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1139/v87-246

upstream raw materials:

methanol

Sisomicin sulfate

1,2-dideoxy-1-nitro-D-manno-heptitol

1,2-dideoxy-4,5;6,7-di-O-isopropylidene-1-nitro-D-manno-heptitol

Downstream raw materials:

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

(1,3/2,4,6)-di-(ethoxycarbonylamido)-1,2,3-cyclohexanetriol

1,3-Bis-N-(benzyloxycarbonyl)-2-desoxystreptamin

2-deoxystreptamine

Refernces

• 1、 Schuerrle, Karsten,Beier, Barbara,Piepersberg, Wolfgang. "Asymmetric Synthesis of cis-1,3-Diamino-1,3-dideoxycyclitols". . p. 2407 - 2412. Retrieved 2007/10/02.
• 2、 Paulsen,Jansen,Stadler. "Building units for oligosaccharides, XXV. Selective degradation of sisomicin to sisamine". . p. 837 - 842. Retrieved 2007/10/02.