6-Amino-3-[glycyl(methyl)amino]-2-hydroxy-4-methoxycyclohexyl 2-amino-2,3,4,6-tetradeoxy-6-(methylamino)hexopyranoside → Carbonate Ion

HRID 848443Notes

Reaction equation

[CH3:1][NH:2][CH2:3][C@H:4]1[O:9][C@H:8]([O:10][C@H:11]2[C@H:16]([OH:17])[C@H:15]([N:18]([C:20]([CH2:22][NH2:23])=[O:21])[CH3:19])[C@@H:14]([O:24][CH3:25])[CH2:13][C@H:12]2[NH2:26])[C@H:7]([NH2:27])[CH2:6][CH2:5]1.CNC[C@H]1[O:36][C@H:35]([O:37][C@H]2[C@H](O)[C@H](N(C(CN)=O)C)[C@@H](OC)C[C@@H]2N)[C@H](N)CC1>>[CH3:1][NH:2][CH2:3][C@H:4]1[O:9][C@H:8]([O:10][C@H:11]2[C@H:16]([OH:17])[C@H:15]([N:18]([C:20]([CH2:22][NH2:23])=[O:21])[CH3:19])[C@@H:14]([O:24][CH3:25])[CH2:13][C@H:12]2[NH2:26])[C@H:7]([NH2:27])[CH2:6][CH2:5]1.[C:35](=[O:37])([O-:9])[O-:36]

Participants

Reactant 2

HCID 1560866-Amino-3-[glycyl(methyl)amino]-2-hydroxy-4-methoxycyclohexyl 2-amino-2,3,4,6-tetradeoxy-6-(methylamino)hexopyranoside

HCID 156088Istamycin B2×

Product 2

HCID 19660Carbonate Ion

HCID 156088Istamycin B

Procedure

Istamycin B is very similar to istamycin A in its properties, and istamycin B is also a basic compound. Istamycin B isolated as a carbonate thereof is in the form of a colorless powder which has no definite melting point, decomposes at 112°-124° C. and gives a specific optical rotation [α]D25 =+165° (c 0.4, water) and of which the elemental analysis is coincident with the theoretical values of the molecular formula C17H35N5O5.1/2H2CO3 (C 49.99%, H 8.63%, N 16.65%, O 24.73%). This molecular formula has been confirmed by high-resolution mass-spectrometry (Found: m/e 389.2625; Calcd. for C17H35N5O5 : m/e 389.2635). The infra-red absorption spectrum of istamycin B hemicarbonate pelleted in potassium bromide is shown in FIG. 2 of the attached drawings. The ultraviolet absorption spectrum of the istamycin B hemi-carbonate in water shows only end absorption. In the proton (1H) nuclear magnetic resonance absorption spectrum (external standard: TMS, pD 5.4) of istamycin B hemi-carbonate in deutero-water, there are shown characteristic signals at δ 3.26 (s, N--CH3), 3.59 (s, N--CH3), 3.95 (s, O--CH3), 4.57 (s, CH2) and 5.96 (d, J=3.5 Hz, CH). Like istamycin A, istamycin B is soluble in water and methanol but sparingly soluble or insoluble in ethanol and other common organic solvents, and it is positive to the ninhydrin reaction and to the Rydon-Smith reaction. As stated hereinbefore, istamycin B is separable from istamycin A by thin layer chromatography on cellulose.

Sources & evidence

ORD record: ord-ba75406e0d4e478c8f03683de8b9a84b
Source dataset: uspto-grants-1981_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04296106

Reaction notes

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