4-O-<6-amino-4-O-(6-amino-2,3,6-trideoxy-α-D-erythro-hexopyranosyl)-2.3.6-trideoxy-α-D-erythro-hexopyranosyl>-2-deoxystreptamine tetrahydrochloride

Base Information

• Chemical Name: 4-O-<6-amino-4-O-(6-amino-2,3,6-trideoxy-α-D-erythro-hexopyranosyl)-2.3.6-trideoxy-α-D-erythro-hexopyranosyl>-2-deoxystreptamine tetrahydrochloride
• CAS No.: 110611-75-1
• Molecular Formula: C₁₈H₃₆N₄O₇*4ClH
• Molecular Weight: 566.35

Synonyms:

Chemical Property of 4-O-<6-amino-4-O-(6-amino-2,3,6-trideoxy-α-D-erythro-hexopyranosyl)-2.3.6-trideoxy-α-D-erythro-hexopyranosyl>-2-deoxystreptamine tetrahydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-<6-amino-4-O-(6-amino-2,3,6-trideoxy-α-D-erythro-hexopyranosyl)-2.3.6-trideoxy-α-D-erythro-hexopyranosyl>-2-deoxystreptamine tetrahydrochloride

There total 16 articles about 4-O-<6-amino-4-O-(6-amino-2,3,6-trideoxy-α-D-erythro-hexopyranosyl)-2.3.6-trideoxy-α-D-erythro-hexopyranosyl>-2-deoxystreptamine tetrahydrochloride 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:

3',4':5,6-di-O-cyclohexylidene-tetra-N-methoxycarbonylneamine (82472-81-9) → 4-O-<6-amino-4-O-(6-amino-2,3,6-trideoxy-α-D-erythro-hexopyranosyl)-2.3.6-trideoxy-α-D-erythro-hexopyranosyl>-2-deoxystreptamine tetrahydrochloride (110611-75-1)

Guidance literature:

Multi-step reaction with 14 steps

1: 83 percent / sodium hydride, N,N-dimethylformamide / 24 h / 25 °C

2: 81 percent / 1:1 acetic acid / 7 h / 56 °C

3: periodic acid / tetrahydrofuran / 1 h

4: 0.15 g / triethylamine / methanol / 24 h / 25 °C

5: 81 percent / sodium methoxide / methanol / 2 h / 70 °C

6: 75 percent / boron trifluoride etherate, triethylamine / CHCl₃ / 2 h / -5 °C

7: 92 mg / hydrogen / 10 percent Pd-C / methanol / 3 h / 1520 Torr

8: 35 mg / MeONa / methanol

9: 1) CCl₄, tris(dimethylamino)phosphine 2) sodium azide / 1) N,N-dimethylformamid, -45 deg C, 1.5 h 2) 60 deg C, 48 h

10: 88 percent / BF₃-etherate, 6-toluene-p-sulphonate, sodium azide, triethylamine / 1,2-dichloro-ethane; dimethylformamide / 1.5 h / -5 °C

11: 96 percent / MeONa / methanol

13: 1) 90 percent aq. hydrazin hydrate 2) hydrogen / 1)Pd-C 2) 20 percent palladium hydroxide / 1) 1-propanol, reflux, 24 h 2) 3.5 atm, 18 h

14: 1) 15 percent hydrochloric acid 2) water / 1) 80 deg C, 3 h 2) 80 deg C, 1 h

With hydrogenchloride; tetrachloromethane; sodium azide; 6-toluene-p-sulphonate; boron trifluoride diethyl etherate; water; hydrogen; sodium methylate; sodium hydride; hydrazine hydrate; acetic acid; periodic acid; triethylamine; N,N-dimethyl-formamide; Hexamethylphosphorous triamide; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)90217-9

Reference yield:

1,3-di-N-benzyl-4-O-<(1R,2R)-2-(N-benzylmethoxycarbonylamino)-1-<(1R)-2-(N-benzylmethoxycarbonylamino)-1-formylethoxy>-2-formylethyl>-5,6-O-cyclohexylidene-2-deoxy-1,3-di-N-methoxycarbonylstreptamine (110537-71-8) → 4-O-<6-amino-4-O-(6-amino-2,3,6-trideoxy-α-D-erythro-hexopyranosyl)-2.3.6-trideoxy-α-D-erythro-hexopyranosyl>-2-deoxystreptamine tetrahydrochloride (110611-75-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 0.15 g / triethylamine / methanol / 24 h / 25 °C

2: 81 percent / sodium methoxide / methanol / 2 h / 70 °C

3: 75 percent / boron trifluoride etherate, triethylamine / CHCl₃ / 2 h / -5 °C

4: 92 mg / hydrogen / 10 percent Pd-C / methanol / 3 h / 1520 Torr

5: 35 mg / MeONa / methanol

6: 1) CCl₄, tris(dimethylamino)phosphine 2) sodium azide / 1) N,N-dimethylformamid, -45 deg C, 1.5 h 2) 60 deg C, 48 h

7: 88 percent / BF₃-etherate, 6-toluene-p-sulphonate, sodium azide, triethylamine / 1,2-dichloro-ethane; dimethylformamide / 1.5 h / -5 °C

8: 96 percent / MeONa / methanol

10: 1) 90 percent aq. hydrazin hydrate 2) hydrogen / 1)Pd-C 2) 20 percent palladium hydroxide / 1) 1-propanol, reflux, 24 h 2) 3.5 atm, 18 h

11: 1) 15 percent hydrochloric acid 2) water / 1) 80 deg C, 3 h 2) 80 deg C, 1 h

With hydrogenchloride; tetrachloromethane; sodium azide; 6-toluene-p-sulphonate; boron trifluoride diethyl etherate; water; hydrogen; sodium methylate; hydrazine hydrate; triethylamine; Hexamethylphosphorous triamide; palladium dihydroxide; palladium on activated charcoal; In methanol; chloroform; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)90217-9

Reference yield:

tetra-N-benzyl-3',4':5,6-di-O-cyclohexylidene-tetra-N-methoxycarbonylneamine (110537-69-4) → 4-O-<6-amino-4-O-(6-amino-2,3,6-trideoxy-α-D-erythro-hexopyranosyl)-2.3.6-trideoxy-α-D-erythro-hexopyranosyl>-2-deoxystreptamine tetrahydrochloride (110611-75-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 81 percent / 1:1 acetic acid / 7 h / 56 °C

2: periodic acid / tetrahydrofuran / 1 h

3: 0.15 g / triethylamine / methanol / 24 h / 25 °C

4: 81 percent / sodium methoxide / methanol / 2 h / 70 °C

5: 75 percent / boron trifluoride etherate, triethylamine / CHCl₃ / 2 h / -5 °C

6: 92 mg / hydrogen / 10 percent Pd-C / methanol / 3 h / 1520 Torr

7: 35 mg / MeONa / methanol

8: 1) CCl₄, tris(dimethylamino)phosphine 2) sodium azide / 1) N,N-dimethylformamid, -45 deg C, 1.5 h 2) 60 deg C, 48 h

9: 88 percent / BF₃-etherate, 6-toluene-p-sulphonate, sodium azide, triethylamine / 1,2-dichloro-ethane; dimethylformamide / 1.5 h / -5 °C

10: 96 percent / MeONa / methanol

12: 1) 90 percent aq. hydrazin hydrate 2) hydrogen / 1)Pd-C 2) 20 percent palladium hydroxide / 1) 1-propanol, reflux, 24 h 2) 3.5 atm, 18 h

13: 1) 15 percent hydrochloric acid 2) water / 1) 80 deg C, 3 h 2) 80 deg C, 1 h

With hydrogenchloride; tetrachloromethane; sodium azide; 6-toluene-p-sulphonate; boron trifluoride diethyl etherate; water; hydrogen; sodium methylate; hydrazine hydrate; acetic acid; periodic acid; triethylamine; Hexamethylphosphorous triamide; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)90217-9

upstream raw materials:

4-O-<6-amino-4-O-(6-amino-2,3,6-trideoxy-α-D-erythro-hexopyranosyl)-2,3,6-trideoxy-α-D-erythro-hexopyranosyl>-5,6-O-cyclohexylidene-2-deoxystreptamine

1L-N¹,N³-dibenzyl-N¹,O⁶-carbonyl-O⁴,O⁵-cyclohexane-1,1-diyl-N³-methoxycarbonyl-2-deoxy-streptamine

6-O-p-tolylsulfonyl-3,4-di-O-acetyl-D-glucal

3',4':5,6-di-O-cyclohexylidene-tetra-N-methoxycarbonylneamine

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